Cozy Cottages in Holmes Beach

Best Cottage Rentals in Holmes Beach

Experience the beauty of Holmes Beach with our selection of delightful cottages, perfect for travelers seeking tranquility and style. Each listing promises a unique getaway experience.

Cottages in Holmes Beach
Seabreeze Cottage
House
5009 2nd Ave, US, Holmes Beach, FL, 34217, USA

Seabreeze Cottage is located in Holmes Beach, just a 4-minute walk from Anna Maria Island and 17 miles from The John and Mable Ringling Museum of Art. This property offers access to a balcony, free private parking, and free Wifi. Outdoor seating is also available at the vacation home. Seabreeze Cottage features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with a hair dryer. Towels and bed linen are featured in the vacation home. For added privacy, the accommodation features a private entrance. Anna Maria City Pier is 2.8 miles from the accommodation, while Greens Of Manatee Golf Club is 12 miles away. Sarasota Bradenton International Airport is 16 miles from the property.

Amenities:

Fireplace/Heating • Parking • Sports/Activities • Security/Safety • Accessibility • Internet • Child Friendly • Pool

Cottages in Holmes Beach
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
Cottage
Holmes Beach, Florida, USA

Our five unit property was featured in the January/February 2020 issue of Southern Living, and we are honored and thrilled!

Welcome to our Cottage! If you are looking for a simple, quiet, stress-free place to enjoy the beach, this is it. It's not a fancy condo-- no long hallways, distant parking, elevators, or crowds-- and there are no streets to cross to reach the beach--just a sandy walk from your screened porch door. The Cottage is a duplex, and this listing is for the larger side. VRBO #327896 will show you the smaller side. The two sides share a screened porch facing the beach.

The cottage was constructed in 1916 or so, as a caretaker's home for a larger house which is now gone. It has been carefully maintained and updated, but has retained the charm of a bygone era.

The interior walls are heart pine, and so are the floors, refinished by hand. Furnishings have been chosen for comfort-- a rattan recliner and matching sleeper sofa in the living room, dining table with leaf (in case you would like to have a guest or two for supper), and king size bed in the bedroom.

The cottage is shaded by ancient Australian pine trees and has a comfortable shared screened porch for a front-row view of the sunsets and stars. With the windows open at night, you can hear the surf!

Walk directly out the screen porch door, and down to the beach--no streets to cross. Or, sit out on the patio and enjoy your coffee and newspaper, or cocktails. Our guests tell us that the best part of the patio area, (besides the view) is it's size-- plenty of room for spreading out.

We are located a block away from the Cafe on the Beach, convenient for all-you-can-eat pancake breakfasts, quick lunches, and relaxing dinners. The beach-front playground is a block and a half away. Take the free trolley and see the rest of the island.

The other side of this duplex, which is a little smaller, VRBO 327896 is also available. See our other units available on the same property, VRBO 82848, 1473396, and 738184.

Keywords: Cottage/Duplex

Guest Reviews:

- "Great Old Florida vibe. Suited our needs perfectly, which was a nice quiet time on a nice quiet beach. All good!" - "Easy to find. Great amenities! Helpful host! Enjoyed the location!" - "Alice was prompt and attentive. Can't beat the location!" - "Weekend getaway with family! Perfect place and location! Cottage has everything you need and we received a sweet welcome basket when we arrived at our cute little cottage! Very nice surprise! The owner was very friendly and caring! I loved the beach chairs, umbrella, and boogie board we had right on our porch to take to the beach. The beach was amazing and only steps away! The shower pressure was the best ever! Plenty of towels. Comfortable and cozy cottage. Great location! We will be back! We made some sweet memories at the charming cottage!!"

Cottages in Holmes Beach
Castaway Cottage
House
307 59th St, Unit A-1, US, Holmes Beach, FL, 34217, USA

Castaway Cottage is located in Holmes Beach, just a 5-minute walk from Anna Maria Island and 18 miles from The John and Mable Ringling Museum of Art. This property offers access to a balcony, free private parking, and free Wifi. Outdoor seating is also available at the vacation home. Castaway Cottage features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are featured in the vacation home. For added privacy, the accommodation features a private entrance. Anna Maria City Pier is 2.3 miles from the accommodation, while Greens Of Manatee Golf Club is 12 miles away. Sarasota Bradenton International Airport is 16 miles from the property.

Amenities:

Pet Friendly • Fireplace/Heating • Security/Safety • Internet • Sports/Activities • Pool • Child Friendly • Parking

Cottages in Holmes Beach
Quiet Nights of Quiet Stars on Anna Maria Island
Cottage
Holmes Beach, Florida, USA

Quiet nights of quiet stars, quiet walks by quiet sea, quiet thoughts on quiet location, oh how lovely . . .

A guest had this to day: "Songbird is a cute little purple house on a quiet side street on Anna Maria Island. I referred to the house as little, it is really quite spacious & comfortable. This is our 6th stay at Songbird & we are looking forward to our next stay. This trip we were on side B but have also stayed on Side A, both are equally as nice.
The kitchen is well stocked with all the cooking essentials. Pots, pans, coffee maker, toaster, blender etc. There is also a charcoal BBQ in the backyard.
The living room is open and airy with a love-seat, comfortable couch & a large TV. The master bedroom has a king bed with a comfortable and supportive mattress. Nightstands, a dresser and closet gives plenty of room to unpack so you won`t feel like you are living out of your suitcase while staying here. The 2nd bedroom is quite large & has twin beds. According to my daughter and travel companion the beds and room are very comfortable.
Washer & dryer are located in a porch outback and shared with people renting the other side of the house. We have never had a problem with this, as knowing it is shared anyone keeps their eye on the laundry and removes it as soon as it is finished.
The wi-fi reaches the backyard and there is free US/Canada wide long distance on the house phone.
I hope this helps with your decision to stay here. We highly recommend it."

Is it perfect? No way, but it is clean and comfortable.

1. The Gulf beach access is 4 blocks but 3 are short blocks and it ends up being 3 in length and having done it a number of times you cut the corners at 64th street and Holmes Blvd and when you arrive at Gulf Drive and 65th there is the beach access and a few parking places. The real good thing is that you don't cross Marina Drive [busy street]. Some guests have driven over and parked or dropped off people and headed back to Songbird and walked back to the beach access.

2. Located in the middle of the block on a quiet street.

3. Free fast wifi and Washer and Dryer at no charge. Hair dryer also.

4. Everpure H-300 under sink mounted water filter with glass filler faucet and hooked up to the ice maker too.

5. There is central air installed in 2019.

6. New refrigerator 2025 with automatic ice maker in the freezer. New stove and microwave too.

7. The BBQ is a charcoal type 2025 and I do not supply coals.

8. The kitchen has been updated with upper white cabinets in early 2000's and is fully stocked with cooking utensils and almost always salt and pepper. Also all linens, towels and so on.

9. New base kitchen cabinets 2025 with a very quiet dishwasher. Quartz countertops.

10. House landline phone provided for local calls and free long distance to North America and Territories. Canadians like this idea a lot.

11. New 2025 King Bed mattress and box spring. New 2025 medium firm twin mattresses and box springs Maximum 4 people and maximum 3 adults minimum age 25.

12. The closest restaurant Ugly Grouper is about 5 blocks and is popular. Scott’s Deli is 3 blocks and top shelf Key Lime Pie.

13. 7 blocks to Island Shopping Center [think 1960] with restaurants, clothing stores, hardware store, art gallery, parrots and more.

14. Holmes Beach public library is 5 blocks away. Sweet library!

15. Updated kitchen and bath fixtures 2025

16. No stairs here as an easy living ground level place.

17. TV is a 65" flat thin screen 2025. Samsung QLED

18. 2 bedrooms and 1 Bathroom with step-in shower.

19. No pets and no smoking. A number of people verify no pets as they have allergies and, yes, no pets.

20. The cleaner has been cleaning for about 3 years and does nice work.

21. The patio is covered and has a table with chairs.

22. Outdoor shower when home from the beach.

23. I supply dish soap, dishwasher pods, hand soap, one or more rolls of paper towels, more than one roll of TP, dish sponge, laundry soap no scent and garbage bags.

24. A free trolley has a stop 1 block away to go north and a stop to go south is 3 blocks at the beach access. 6am-10pm and runs at 20 minute intervals.

25. Parking space for two cars.

26. Backyard is a nice size.

I have found that people arrive and unload luggage and head to the beach. The busiest street on the island in this spot is Marina Drive and you do NOT cross it on the way to the beach. The access is a 3-4 block stroll. And the property is located in the middle of the street not on a busy corner or street.

Again, thank you for your time.

Guest Reviews:

- "What you see on line is what you get. Small space as advertised great for a single or couple. Clean and efficient. Host was great with any support needed. This is old Florida type cottage. Great central location on the island. Make sure to stop at Scotty's Deli." - "We had a wonderful stay!The place was spotless and very well-maintained.The location couldn't be better-just a short walk to the beach and super convenient for getting around the island.Everything was exactly as described, and communication with the host was smooth and easy. Highly recommend for anyone looking for a relaxing beach getaway. "

Cottages in Holmes Beach
Sea Palm Cottage
House
Ilexhurst, FL, USA

Sea Palm Cottage offers accommodations in Ilexhurst, 15 miles from The John and Mable Ringling Museum of Art and 4.1 miles from Anna Maria City Pier. The air-conditioned accommodation is a 3-minute walk from Holmes Beach. The vacation home also offers facilities for disabled guests. Offering a patio, this vacation home also has a satellite TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a walk-in shower and a hair dryer. The property has an outdoor dining area. Guests can enjoy the outdoor swimming pool at the vacation home. Greens Of Manatee Golf Club is 10 miles from Sea Palm Cottage. Sarasota Bradenton International Airport is 13 miles away.

Amenities:

Accessibility • Laundry • Child Friendly • Air Conditioner • Guest Services • Pool • Fireplace/Heating • Barbecue/Outdoor Cooking • Security/Safety • Wheelchair Accessible • Balcony/Terrace

Cottages in Holmes Beach
END OF SUMMER RATES! Cozy cottage central location-Private patio-3 min to beach!
Cottage
Holmes Beach, Florida, USA

Discover this boutique-styled cottage and the white sandy beaches that make Anna Maria Island so famous. The Cottage is just 20 yards from the Gulf ocean and is one house off the beach as the crow flies.

A large open room with lots of sunlight will give your vacation the perfect vibe. The modern kitchen is fully loaded with a dishwasher, microwave, stove and a fridge...and of course there's an ice maker! Plus lots of storage for longer stays makes this cozy kitchen easy to enjoy.

The comfortable living room is a great place to chill. Wifi and television will also keep you occupied if you've had enough sun. Fans in the living and bedroom mean you can enjoy the perfect weather without sacrificing airflow. Naturally, if you like it cooler, AC is always available. Need extra sleeping room? The living room features a very comfortable pull-out couch for guests.

The bathroom has a tub for soaking and a marble-topped vanity as well as custom one-of-a kind touches. The clean, white fluffy towels are all 100% cotton and will give you that fresh hotel feel.

Your bedroom comes with a high-end king bed that's not too firm, not too soft, and comes with 450-thread count cotton sheets. The room offers bedside reading lamps, a large closet and private television.

Just think... when the waves pick up, you can hear the ocean from your private patio, which is a great place to relax all day when you're not out on the beach. Feeling like a BBQ? Kick on the grill and enjoy.

This house has everything you could possibly need to enjoy time by the sea.

Your boutique chic, adorable cottage is just a 2-minute walk to coffee shops, the only late-night watering hole on the island, the local Walgreens, and a bike rental store so you never need to drive anywhere. But if you did want to head out, the free trolley that runs up and down the island makes getting around a cinch!

Lastly there is a washer & dryer located on the back of the property— this laundry area is shared by our two cottages (we have this "Sun Cottage" and a "Surf Cottage" which you can see on our website if you google Postcard Cottages AMI)

Guest Reviews:

- "Loved the property and the location. Only steps to the beach." - "First I wanted to say thanks for the fun place.They said it was a 3 minute walk to the beach, they were wrong, more like one. Easy walk. Great location to everything. Place looks just like you see. Bed was Fabulous and everything you need in kitchen. Will be back. Great beach location" - "This little cottage was absolutely perfect for my wife and I to enjoy Anna Maria Island. I was pleased that the owner was quick to respond to a couple questions I had before our arrival. It made for such a relaxing trip. The cottage itself was very clean, comfortable and well decorated, with a nice array of kitchen utensils and a great back patio. We really enjoyed the location as it was in between the busier areas of the island. It made for a beach that was not very crowded. It is an easy two minute walk to the beach, and the owners even have a wagon, beach chairs, umbrella, and floats. All you need for a day at the beach . The location also made for a short drive in either direction to see all the island has to offer. I would certainly stay here again."

Cottages in Holmes Beach
Sea Spray Private Beach Cottage
House
130 51st Street, Holmes Beach, FL, 34217, USA

Sea Spray Private Beach Cottage offers accommodations in Holmes Beach, 17 miles from Sarasota International Convention Center and 17 miles from John and Mable Ringling Museum of Art. Located around 17 miles from The John and Mable Ringling Museum of Art, the vacation home is also 2.7 miles away from Anna Maria City Pier. Free Wifi is available throughout the property and Anna Maria Island is a 4-minute walk away. The air-conditioned vacation home also offers a flat-screen TV, a fully equipped kitchen with a dishwasher, a seating area, washing machine, and 2 bathrooms with a bath and a shower. For added privacy, the accommodation features a private entrance. Guests at the vacation home will be able to enjoy activities in and around Holmes Beach, like cycling. Sarasota Bradenton International Airport is 16 miles from the property.

Amenities:

Air Conditioner • Barbecue/Outdoor Cooking • Laundry • Parking • Security/Safety • Fireplace/Heating • Internet • Ocean View • Other • Sports/Activities • View • Guest Services

Cottages in Holmes Beach
Coastal Home with Heated Pool, Close to Beach!
Cottage
Holmes Beach, Florida, USA

Pineapple Palms by Anna Maria Island Accommodations
308 64th St, Holmes Beach, FL 34217
VRC17-000041

Welcome to Pineapple Palms, the ultimate ocean-loving getaway just two-and-a-half blocks from the stunning beaches of Holmes Beach! Perfect for a small family or friends, this charming two-bedroom, two-bathroom home offers a private heated pool, lush, landscaped backyard, and a breezy open concept living space. Nestled just minutes from Anna Maria’s pristine shores, shops, and dining, Pineapple Palms is your perfect island retreat for fun, relaxation, and making lifelong memories!

Highlights
• 6-minute Walk to Holmes Beach
• 2 bedroom / 2 baths
• 1 King, 2 Twin beds
• Heated pool
• Outdoor dining
• Blackstone Grill
• Close to Marina Drive for shopping, dining, and local attractions
• 2 Car Parking

Enjoy your mornings or evenings on the paver deck around the private heated pool, surrounded by tropical landscaping for complete privacy. Fire up the Blackstone grill and gather around the outdoor dining table for delicious alfresco meals. After a day at Anna Maria’s beaches, unwind here with a cold drink or share a poolside laugh with family or friends. Just moments from the sand, shops, and local eateries, Pineapple Palms is your gateway to the perfect island escape.

Step inside this cozy island oasis to discover a stylish, open layout living area featuring tile floors and beautiful granite countertops in the kitchen. The nearby dining table seats four, perfect for family meals or inviting friends over. Relax in the sitting area with plush furnishings and a flat-screen TV, creating a peaceful spot to unwind after a day at the beach.

Retreat to the luxurious king bedroom, complete with a TV and an ensuite bath that includes a walk-in shower, your private sanctuary for rest and relaxation. The second bedroom, furnished with two twin beds, offers a bright and cheerful space for kids or guests. A hall bathroom with a shower and tub combo provides an additional convenient space for everyone. Perfectly suited for up to four people, Pineapple Palms ensures a restful night’s sleep for all.

Room Details
• Primary Bedroom: King bed, ensuite bathroom with walk-in shower
• Second Bedroom: Two twin beds

Book Pineapple Palms today and immerse yourself in the relaxed island lifestyle. With its unbeatable location, private pool, and cozy interiors, this charming home is the perfect spot for relaxing, exploring, and creating lifelong memories on Anna Maria Island!

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There are no pets allowed in this home.

*Please note: 2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

This home is managed by AMI Accommodations, an Anna Maria Island property management company.

We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.

Please see our AMI Accommodations Rental Policies for full details.

Please Remember:
"You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property."
*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Guest Reviews:

- "Proximity to the beach was great, not much of a walk at all compared to other places we have stayed. Appreciated the heavy-duty wagon, chairs and umbrellas for use at the beach. Also liked the addition of the washer and dryer. When we originally inquired before locking down the rental we were told there was none. Pool area was awesome - like our own tropical oasis ... that was the best part of the property. Enjoyed the balcony off the kitchen too. Teens enjoyed their own private balcony as well. Plenty of room for 4 people (2 adults and 2 teens). Thanks for the memories!"

Cottages in Holmes Beach
Coconut Cottage #3
House
108 39th St, Unit #3, US, Holmes Beach, FL, 34217, USA

Coconut Cottage #3 is located in Holmes Beach, just a 2-minute walk from Holmes Beach and 17 miles from The John and Mable Ringling Museum of Art. This property offers a private pool, free Wifi, and free private parking. The accommodation provides a 24-hour front desk. This vacation home includes 2 bedrooms, a living room and a flat-screen TV, an equipped kitchen with a dining area, and 2 bathrooms with a bath and a washing machine. Towels and bed linen are provided in the vacation home. For added privacy, the accommodation features a private entrance. Anna Maria City Pier is 3.5 miles from the vacation home, while Greens Of Manatee Golf Club is 11 miles away. Sarasota Bradenton International Airport is 15 miles from the property.

Amenities:

Parking • Pet Friendly • Internet • Guest Services • Sports/Activities • Pool • Security/Safety • Child Friendly

Cottages in Holmes Beach
Home with Private Pool, Two Blocks from the Beach! - Queen Palms
Cottage
Holmes Beach, Florida, USA

Queen Palm by Anna Maria Island Accommodations
5701 Holmes Blvd, Unit B (North), Holmes Beach, FL 34217
VRC19-000042

Welcome to Queen Palm by Anna Maria Island Accommodations, a cozy two-bedroom, one-bath ground-level retreat located less than a five-minute walk from the white-sand shores of Holmes Beach. Perfect for couples, small families, or friends, this tropical hideaway offers the perfect blend of comfort, convenience, and coastal charm. With a private pool, lush outdoor lounge area, and proximity to local restaurants, shops, and the free island trolley, Queen Palm sets the stage for a relaxing and memorable Anna Maria Island getaway.

Highlights
•6-minute walk to Holmes Beach
• 2 Bedrooms / 1 Bathroom
• 2 King beds and Full sleeper sofa
• Private pool
• BBQ grill and outdoor dining area
• Washer and dryer
• Outdoor shower
• Outdoor seating
• 2 parking spaces

Spend your days basking in the sun beside your private pool, surrounded by tropical palms and soft breezes. Cool off with a dip, rinse off at the outdoor shower, and fire up the BBQ grill for an easy, laid-back dinner. With plenty of seating for lounging or dining poolside, Queen Palm makes outdoor living effortless, perfect for relaxing afternoons and cozy evening gatherings under the stars.

Step inside to a bright living space designed for comfort and connection. The family room features two plush sofas, a comfy accent chair, and a large TV for streaming your favorite shows. The modern kitchen comes equipped with stainless steel appliances, cookware, and all the essentials to prepare meals with ease. Enjoy casual bites at the indoor table for four or savor your meal outdoors at the poolside dining table for a true island experience.

Each bedroom is a relaxing retreat with king beds, vibrant decor, and TVs, creating a cheerful yet soothing coastal atmosphere. The shared hall bathroom includes a convenient shower/tub combination, perfect for families. For additional sleeping flexibility, the living room offers a full sleeper sofa, and guests will appreciate the stacked washer and dryer for extended stays or easy clean-ups after beach days.

Room Details
-Primary Bedroom: King bed, TV
-Second Bedroom: King bed, TV
-Living Room: Full sleeper sofa

Queen Palm offers two parking spaces, a washer and dryer, and easy access to Holmes Beach and local attractions. Stroll to nearby restaurants, explore the island boutiques, or hop on the free Anna Maria Island trolley to discover everything the island has to offer. Whether you’re swimming, sunbathing, or simply relaxing by the pool, this Holmes Beach vacation home promises a stay filled with sunshine and serenity.

With its prime location, private pool, and inviting coastal charm, Queen Palm by Anna Maria Island Accommodations is the perfect retreat for your next Anna Maria Island vacation. Relax, unwind, and create lasting memories in this little slice of paradise.
Book your stay at Queen Palm today!

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There are no pets allowed in this home.

2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

This home is managed by Anna Maria Island Accommodations Accommodations, an Anna Maria Island property management company.

We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.

Please see our Anna Maria Island Accommodations Accommodations Rental Policies for full details.

Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Guest Reviews:

- "The home is definitely on the small side, but beautifully decorated and furnished. It was the perfect size for myself, and my three children. The pool was beautiful and very clean. The only thing I would change is to have access to the pool from inside the house - but that isn't a big deal. The kitchen had everything we needed to make a meal, the bedrooms were nice and clean. The bathroom was very nice, and they provided plenty of linens of the 4 of us. The washer/dryer was a plus for sure. The location was nice and only about a 5 minute walk to the beach access. Would definitely recommend this property to anyone interested in staying on Holmes beach/AMI!"

Cottages in Holmes Beach
Modern Beach Cottage with Heated Pool Close to Beach
House
5802 Imperiore Ave, Holmes Beach, FL, 34217, USA

Modern Beach Cottage with Heated Pool Close to Beach is located in Holmes Beach, just a 2-minute walk from Anna Maria Island and 17 miles from The John and Mable Ringling Museum of Art. This property offers a private pool and free Wifi. Guests can use a terrace. The air-conditioned vacation home consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a kettle, and 2 bathrooms with a shower. The accommodation is non-smoking. Anna Maria City Pier is 2.3 miles from the vacation home, while Greens Of Manatee Golf Club is 12 miles from the property. Sarasota Bradenton International Airport is 15 miles away.

Amenities:

Internet • Other • Fireplace/Heating • Child Friendly • Security/Safety • Pool • Balcony/Terrace • View • Pet Friendly • Air Conditioner

Cottages in Holmes Beach
Charming Ground Level Resort Style 3 units Condo of a TRIPLEX- unit A
Cottage
Holmes Beach, Florida, USA

Welcome to our newly updated ground level 2 beds/2bath unit A of the triplex located on the southern end of Holmes Beach, just a few steps from the beach(2-3 min walk).
There are no busy streets to cross and even footpath to the beach leading from the back of the property. We had minimal hurricane damage- just change flooring and updated furniture.
Large shared pool is located in the backyard as well as a separate patio and grill for each unit.
You have the option to heat the pool. Your room charge covers the the pool temperature up to 75F. It’s additional $150 for week stay or less to heat the pool above 75F.
Please let us know if you wish to heat the pool so we have it ready for your upcoming stay. Fire pit for colder nights is a great addition to all amenities.
Washer and dryer in each unit for your use. The property includes free wireless internet. Each unit has been updated and is comfortably furnished. We provide beach towels, beach chairs and beach trolley as well. Kitchen is fully equipped.It's quiet, yet close to shopping, restaurants and trolley stops.

Guest Reviews:

- "The unit is amazing and we loved it! There was actually kitchen supplies that other properties we have stayed at previous years didn’t have which was nice. The pool and outside was so pretty. Beach is walking distance and had great quality beach things. Would recommend more umbrellas for beach goers since there was only one during our stay but overall no issues there. Would recommend more towels for showering in unit as well. Beds were so comfortable and any time we needed to contact owner she was very fast at responding. Recommend 10/10 and will stay again! Thank you 💕"

Cottages in Holmes Beach
Beach Cottage with Heated Pool Short Walk to Beach
House
5805 Imperiore Ave, Holmes Beach, FL, 34217, USA

Beach Cottage with Heated Pool Short Walk to Beach is located in Holmes Beach, just a 2-minute walk from Anna Maria Island and 17 miles from The John and Mable Ringling Museum of Art. This property offers a private pool, free Wifi, and free private parking. Guests can use a terrace. Offering a patio, this vacation home also has a cable TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a shower and a hair dryer. The accommodation is non-smoking. Anna Maria City Pier is 2.3 miles from the vacation home, while Greens Of Manatee Golf Club is 12 miles away. Sarasota Bradenton International Airport is 15 miles from the property.

Amenities:

Parking • Child Friendly • Balcony/Terrace • Fireplace/Heating • Internet • Other • Security/Safety • Pool • Air Conditioner • View

Cottages in Holmes Beach
Cozy Cottage for 4 located steps from the beach. Heated Pool in private Patio.
Cottage
Holmes Beach, Florida, USA

Welcome to Yellowfin Cottage located just 2 houses from the Gulf beaches on Anna Maria Island. Yellowfin Cottage is a ground floor half duplex with 2 beds, 1 bath and its own private patio surrounded by tropical landscaping where you can enjoy the heated pool and outdoor shower. Inside you will find a generous amount of space through out the living room and kitchen area. The kitchen area includes bar seating and is open to the living area for easy entertaining. During the day take the provided beach wagon, chairs and umbrella down to the beach or enjoy some time around the pool. Relax in the living room or retreat to the master suite where you will enjoy our comfortable beds complete with 600 thread count wrinkle free sheets. This home includes a fully equipped kitchen, linens, towels, beach towels, and a Weber grill.

Lizzie Lu's Island Retreat is a full-service property manager on Anna Maria Island to ensure our guests enjoy some of the nicest, well stocked homes on the island. For an additional charge, we offer GEM cars among other services. Rest assured we are here to assist as needed in the most efficient manner possible.
While vacationing on Anna Maria Island, please adhere to our local rules and regulations for our residential community which are included in our homes as well as our arrival information.

City ordinance requires us to inform you that you are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.
Holmes Beach Rental License VRC16-000331

Guest Reviews:

- "The cottage we stayed in was awesome. Clean with all new appliances. The backyard area and pool was perfect for us and our dog. Very short walk to the beach. Lizzie Lu’s Island Retreat did a magnificent job." - "Clean. All needed amenities. Close to beach." - "This was exactly what we needed. We haven’t taken a vacation in several years. It was quiet, so close to the beach, clean and close to the things we needed. Everyone we had interaction with through this property were very professional and nice. The small pool in the back yard was perfect for our day of recovery from Universal Studios. Thank you so much for allowing us to stay here."

Cottages in Holmes Beach
Coveside Cottage
House
204 73rd St, US, Holmes Beach, FL, 34217, USA

Coveside Cottage is located in Holmes Beach, just a 3-minute walk from Anna Maria Island and 19 miles from The John and Mable Ringling Museum of Art. This property offers a private pool, free Wifi, and free private parking. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are available in the vacation home. For added privacy, the accommodation features a private entrance. Anna Maria City Pier is 1.6 miles from Coveside Cottage, while Greens Of Manatee Golf Club is 13 miles from the property. Sarasota Bradenton International Airport is 17 miles away.

Amenities:

Pool • Parking • Fireplace/Heating • Internet • Child Friendly • Sports/Activities • Security/Safety

Cottages in Holmes Beach
Prices cut by 20% for stays up to 31.01.26 - Seabreeze Cottage moments from the beach
Cottage
Holmes Beach, Anna Maria Island, Florida, USA

Seabreeze Cottage is situated on a quiet road with access to the beach, via a leafy lane, just 200 feet away.

The property, which is accessed via a set of exterior steps, is very well furnished and equipped offering everything we hope you would need to enjoy the perfect holiday. The master bedroom has a King size bed and benefits from an en-suite bathroom with bath with overhead shower, basin and WC. The 2nd bedroom has Twin beds which can be joined to make a King and the family bathroom has a shower, basin and WC. The sofa in the sitting room can also be made into a bed which allows the property to sleep up to 6 people.

As the property is built up on stilts it benefits from a lovely raised wooden deck area which is resonably private thanks to the palms trees and shrubs surrounding it. There is off street parking for 1 car (maybe 2 depending on size).

Shops, bars and restaurants can be found within easy walking distance and the free trolley bus stop is just a few minutes walk away which enables you to venture further afield on the island without having to use your car.

Guest Reviews:

- "This was our second stay at Seabreeze. It was just as perfect as our previous stay. Cottage was clean and well stocked. Hopefully you never have to contact Sheron, but if you do, just know she is amazing to work with. Beach is close and not too crowded. Can’t wait to return again." - "The location was awesome! House is close to the beach and far away from the main road so it stays quiet at night! House was clean. The property needs some updates, specifically electrical work and and a washer and dryer update. The lights sometimes flicker and multiple lightbulbs were burned out outside. The deck had a hazard issue as a piece of wood cracked and is sticking out, very easy to trip over and get hurt. We tripped over it multiple times. Thanks!"

Cottages in Holmes Beach
Coconut Cottage #4
House
108 39th St, Unit #4, US, Holmes Beach, FL, 34217, USA

Coconut Cottage #4 is located in Holmes Beach, just a 2-minute walk from Holmes Beach and 17 miles from The John and Mable Ringling Museum of Art. This property offers access to a balcony, free private parking, and free Wifi. The accommodation features a 24-hour front desk. The air-conditioned vacation home is composed of 2 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. Towels and bed linen are offered in the vacation home. For added privacy, the accommodation features a private entrance. Anna Maria City Pier is 3.5 miles from the vacation home, while Greens Of Manatee Golf Club is 11 miles from the property. Sarasota Bradenton International Airport is 15 miles away.

Amenities:

Guest Services • Child Friendly • Internet • Security/Safety • Pool • Sports/Activities • Pet Friendly • Parking

Cottages in Holmes Beach
Two Bedroom Cottage with Tropical Landscaping Surrounding Private Heated Pool!
Cottage
Holmes Beach, Florida, USA

Welcome to Surf Camp Cottage located just 3 houses down from the Gulf beaches of Anna Maria Island. Surf Camp Cottage is a ground level half duplex with 2 bedrooms, 1 and a half baths and its own private patio surrounded by tropical landscaping where you can enjoy the heated pool, outdoor shower and Weber grill. In the garage, you will find a beach wagon, chairs and umbrella for a relaxing day at the beach. Inside you will find the spacious living area with sliding doors onto the patio. The fully equipped kitchen has bar seating for 4 and is open to the living area for easy entertaining. In the evening you can retreat to the master suite where you will enjoy the comfortable king size bed with 600 thread count prima cotton wrinkle free sheets. Linens, towels and beach towels are included in the cottage.

Lizzie Lu's Island Retreat is a full-service property manager on Anna Maria Island to ensure our guests enjoy some of the nicest, well stocked homes on the island. For an additional charge, we offer GEM cars among other services. Rest assured we are here to assist as needed in the most efficient manner possible.
While vacationing on Anna Maria Island, please adhere to our local rules and regulations for our residential community which are located in our homes as well as our arrival information.

City ordinance requires us to inform you that you are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.
Holmes Beach Rental License VRC16-000375

Guest Reviews:

- "Surf Club was spotlessly clean, very well appointed, and the private spool was delightful! Just steps from the beach, we enjoyed the beach chairs, umbrella, and wagon included with the rental. We will definitely be back next year!" - "Absolutely loved Surf Camp and when we go back to Anna Maria Island, we hope to stay there again. The pool was perfect and being so close to the beach was amazing. The amenities were top notch! The only thing we wished they had is some throw blankets for the living room. We loved that the beach house came with a wagon, beach chairs, umbrella, cooler, speaker and beach towels. We rented a gem car and a cabana for the week which they drop off at your door. Absolutely perfect!"

Cottages in Holmes Beach
Crosswind Cottage by Beach Retreats
House
312 A 61st Street, Holmes Beach, FL, 34217, USA

Crosswind Cottage by Beach Retreats offers accommodations in Holmes Beach, a 7-minute walk from Anna Maria Island and 18 miles from The John and Mable Ringling Museum of Art. There's a restaurant and guests can enjoy the water park. The vacation home features an outdoor swimming pool, spa center, and an elevator. Accommodation for disabled guests is also available at the property. The spacious vacation home includes 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, as well as a coffee machine. A TV with cable channels and a DVD player are available. The accommodation is non-smoking. A children's playground is also available at the vacation home, while guests can also relax in the garden. Anna Maria City Pier is 2.2 miles from Crosswind Cottage by Beach Retreats, while Greens Of Manatee Golf Club is 13 miles from the property. Sarasota Bradenton International Airport is 16 miles away.

Amenities:

Breakfast • View • Pet Friendly • Sports/Activities • Child Friendly • Other • Restaurant • Spa • Fireplace/Heating • Wellness Facilities • Guest Services • Pool

Cottages in Holmes Beach
Anna Maria Cottage with Golf Cart
Cottage
Holmes Beach, Florida, USA

This charming Anna Maria Island Vacation Home located close to restaurants, shopping, boat ramp, tennis/pickle ball, playground, dog parks and of course the white sand beaches! If looking for a different length of stay just reach out and we can see what we have available.

Holmes Beach is a small town on Anna Maria Island in the Gulf of Mexico just south of Tampa Bay. It boasts miles of gorgeous white, sandy beaches, emerald Gulf waters, and abundant sunshine.

The Anna Maria Cottage is a ground floor, one level, end unit home close to everything and comes with a golf cart to get around!

Once inside, the Beach House feel will surround you with an open floor plan, lively colors, and tiled floors. This two-bedroom, one-bath home features upgraded kitchen and bathroom for a comfortable stay. Beautiful patio at the front and rear of the house allows you to relax comfortably on the tropical
island with comfortable furniture. There is a grill in the backyard for your grilling pleasure.

In addition, a golf cart is provided for you to explore the island, go to the beaches, eat of the local restaurants or shop the beachy boutiques on the island. We also have beach chairs and umbrellas for a relaxing day at the beach or kayak on the bay with the two person kayak provided for our guests to use.

Our house is located at the end of a five home complex, on the quiet north end of the island with easy access to the free trolley that runs daily along the island and is also within walking or biking distance of several island shops.

Relax and let the sunsets begin!

Pets are allowed at our home.

You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.

Guest Reviews:

- "Me and my husband came here for our honeymoon, and we had a great time! The house was super cute and within about 10 minutes of everything we wanted to do!" - "This property was clean when we arrived and it was perfect for our family. Lynda and Martin are great with communication and they even provide a book to let you know about local restaurants, shops and places they recommend to visit. We really enjoyed our stay!" - "Great stay! Would recommend renting from these folks! Thanks again we really enjoyed our stay and will book again!"

Holmes Beach Family Friendly Cottages

Holmes Beach Cottages with Parking

Holmes Beach Pet Friendly Cottages

Holmes Beach Cottages with Entertainment

Holmes Beach Cottages with Private Pool

Holmes Beach Cottages with Spa

Holmes Beach Cottages on the Map

Compare the Best Cottages in Holmes Beach – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Seabreeze Cottage 5009 2nd Ave, US, Holmes Beach, FL, 34217, USA 351 4.0 8.0 1 Click here
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1 Holmes Beach, Florida, USA 312 10.0 90 Click here
Castaway Cottage 307 59th St, Unit A-1, US, Holmes Beach, FL, 34217, USA 606 4.0 8.0 1 Click here
Quiet Nights of Quiet Stars on Anna Maria Island Holmes Beach, Florida, USA 150 10.0 70 Click here
Sea Palm Cottage Ilexhurst, FL, USA 706 4.0 5.0 1 Click here
END OF SUMMER RATES! Cozy cottage central location-Private patio-3 min to beach! Holmes Beach, Florida, USA 276 10.0 68 Click here
Sea Spray Private Beach Cottage 130 51st Street, Holmes Beach, FL, 34217, USA 261 4.0 1 Click here
Coastal Home with Heated Pool, Close to Beach! Holmes Beach, Florida, USA 279 10.0 31 Click here
Coconut Cottage #3 108 39th St, Unit #3, US, Holmes Beach, FL, 34217, USA 306 4.0 1 Click here
Home with Private Pool, Two Blocks from the Beach! - Queen Palms Holmes Beach, Florida, USA 281 10.0 26 Click here
Modern Beach Cottage with Heated Pool Close to Beach 5802 Imperiore Ave, Holmes Beach, FL, 34217, USA 346 4.0 1 Click here
Charming Ground Level Resort Style 3 units Condo of a TRIPLEX- unit A Holmes Beach, Florida, USA 389 10.0 25 Click here
Beach Cottage with Heated Pool Short Walk to Beach 5805 Imperiore Ave, Holmes Beach, FL, 34217, USA 363 4.0 1 Click here
Cozy Cottage for 4 located steps from the beach. Heated Pool in private Patio. Holmes Beach, Florida, USA 285 10.0 20 Click here
Coveside Cottage 204 73rd St, US, Holmes Beach, FL, 34217, USA 435 4.0 1 Click here
Prices cut by 20% for stays up to 31.01.26 - Seabreeze Cottage moments from the beach Holmes Beach, Anna Maria Island, Florida, USA 218 10.0 19 Click here
Coconut Cottage #4 108 39th St, Unit #4, US, Holmes Beach, FL, 34217, USA 450 4.0 1 Click here
Two Bedroom Cottage with Tropical Landscaping Surrounding Private Heated Pool! Holmes Beach, Florida, USA 367 10.0 17 Click here
Crosswind Cottage by Beach Retreats 312 A 61st Street, Holmes Beach, FL, 34217, USA 463 4.0 1 Click here
Anna Maria Cottage with Golf Cart Holmes Beach, Florida, USA 324 10.0 16 Click here

Note: The prices for each Cottages in Holmes Beach do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Cottages in Holmes Beach that include a pool or hot tub include:

  • Seabreeze Cottage.- Review Count: 1, Rating: 8.0
  • Castaway Cottage.- Review Count: 1, Rating: 8.0
  • Sea Palm Cottage.- Review Count: 1, Rating: 5.0

These cottages in Holmes Beach offer spa or wellness amenities:

  • Crosswind Cottage by Beach Retreats.- Review Count: 0, Rating: 0.0
  • Castaway Cottage.- Review Count: 0, Rating: 0.0

Family-friendly cottages in Holmes Beach include:

  • Seabreeze Cottage.- Review Count: 1, Rating: 8.0
  • Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1.- Review Count: 90, Rating: 10.0
  • Castaway Cottage.- Review Count: 1, Rating: 8.0

Pet-friendly cottages in Holmes Beach include:

  • Castaway Cottage.- Review Count: 1, Rating: 8.0
  • END OF SUMMER RATES! Cozy cottage central location-Private patio-3 min to beach!.- Review Count: 68, Rating: 10.0
  • Coconut Cottage #3.- Review Count: 0, Rating: 0.0

Cottages in Holmes Beach that include breakfast or meal options include:

  • Crosswind Cottage by Beach Retreats.- Review Count: 0, Rating: 0.0

Cottages in Holmes Beach offering on-site parking include:

  • Seabreeze Cottage.- Review Count: 1, Rating: 8.0
  • Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1.- Review Count: 90, Rating: 10.0
  • Castaway Cottage.- Review Count: 1, Rating: 8.0

Some of the best Cottages in Holmes Beach are:

  • Seabreeze Cottage.- Review Count: 1, Rating: 8.0
  • Castaway Cottage.- Review Count: 1, Rating: 8.0
  • Sea Palm Cottage.- Review Count: 1, Rating: 5.0

Some of the popular Cottages in Holmes Beach are:

  • Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1.- Review Count: 90, Rating: 10.0
  • Quiet Nights of Quiet Stars on Anna Maria Island.- Review Count: 70, Rating: 10.0
  • END OF SUMMER RATES! Cozy cottage central location-Private patio-3 min to beach!.- Review Count: 68, Rating: 10.0