Best Vacation Rentals in Big Pine Key

Fishermen`s Paradise offers accommodations in Big Pine Key, 15 miles from Seven Mile Bridge and 22 miles from Captain Hook S Marina Dive Center. This vacation home is 22 miles from A Deep Blue Dive Center. Free Wifi is available throughout the property and Florida Keys Aquarium Encounters is 21 miles away. The air-conditioned vacation home is composed of 3 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 4 bathrooms. Guests can enjoy a meal on an outdoor dining area while overlooking the sea views. For added privacy, the accommodation features a private entrance. Guests can enjoy the outdoor swimming pool at the vacation home. Key West International Airport is 29 miles away.

Barbecue/Outdoor Cooking • Pool • Security/Safety • Internet • Child Friendly • Laundry

- "We loved that our room opened up directly to the beach and water! There were several thoughtful touches, including artwork and decor in the room that was unique and clearly not mass produced. The breakfast far exceeded our expectations in taste and setting. Each morning we were served a hot breakfast while sitting in the open atrium with the sea breeze. An extra bonus was the Key Deer - an endangered species - that were curious and friendly! We highly recommend this spot - convenient enough to get to Key West or any snorkel/diving experiences - but a world away in terms of quiet beauty."

Sunset Villa offers accommodations in Big Pine Key, 24 miles from Florida Keys Aquarium Encounters and 18 miles from Seven Mile Bridge. The vacation home has access to a restaurant. Captain Hook S Marina Dive Center is 24 miles away and A Deep Blue Dive Center is 25 miles from the vacation home. Leading onto a balcony, the air-conditioned vacation home consists of 3 bedrooms. Offering a terrace with sea views, 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 at the vacation home will be able to enjoy activities in and around Big Pine Key, like cycling. Key West International Airport is 29 miles away.

Security/Safety • Sports/Activities • Restaurant • Child Friendly • Air Conditioner • Guest Services • Laundry • Fireplace/Heating • Balcony/Terrace • Pet Friendly

Beachfront bed & breakfast for sun and fun
A rooftop terrace, free use of bicycles, and gas grills are available at this smoke-free bed & breakfast. Free WiFi in public areas and free self parking are also provided.
Change of towels is available on request.
Barnacle Resort offers 6 accommodations with air conditioning. Flat-screen televisions come with satellite channels.

Bathrooms include showers with rainfall showerheads. This Big Pine Key bed & breakfast provides complimentary wireless Internet access. Change of towels and change of bedsheets can be requested. Housekeeping is provided daily.

- "Beautiful property and excellent host. Loved it! " - "Feels exclusive. Nice staff, great views. Key West about 55 minutes away" - "Very nice place. Good staff." - "No communication when I couldn’t get into my room. Horrible situation. DO NOT STAY AT THIS PROPERTY!! Total scam. " - "Beautiful place to stay - very quiet and away from all the crowds! Exactly what we were looking for - thank you!" - "The staff was great! But the gem of the property is the seclusion with the amazing view of the ocean…Absolutely stunning! Loved it…Would stay there again!"

Big Pine Key Dreams offers accommodations in Big Pine Key, 25 miles from Florida Keys Aquarium Encounters and 19 miles from Seven Mile Bridge. The vacation home has access to a restaurant. The vacation home also offers facilities for disabled guests. The air-conditioned vacation home consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a walk-in shower and a hair dryer. Towels and bed linen are provided in the vacation home. The property has an outdoor dining area. Guests at the vacation home will be able to enjoy activities in and around Big Pine Key, like cycling. Captain Hook S Marina Dive Center is 25 miles from Big Pine Key Dreams, while A Deep Blue Dive Center is 26 miles away. Key West International Airport is 30 miles from the property.

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

While you're here, you can enjoy all the comforts of home and more, including a fenced pool and a full-sized refrigerator/freezer, as well as a stovetop and free WiFi. Other amenities include towels, a picnic area, a dining area, and housekeeping.

- "Remote and plenty of dark sky." - "We love the place!! " - "Amazing stay in a boat!" - "Friendly staff. Property as described." - "Love this place and the staff. Friendly and helpful and the area is relaxing and beautiful " - "Staff was friendly and accommodating. Will definitely book again next vacation." - "Very pleasant and relaxing atmosphere." - "The cottage was in great condition and had everything for a great stay! Had fun connecting with Tiffany and exploring Marathon, FL!"

Hellenga Haven offers accommodations in Big Pine Key, 25 miles from Captain Hook S Marina Dive Center and 26 miles from A Deep Blue Dive Center. The air-conditioned accommodation is 19 miles from Seven Mile Bridge. Free Wifi is available throughout the property and Florida Keys Aquarium Encounters is 25 miles away. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with a hair dryer. Guests can enjoy a meal on an outdoor dining area while overlooking the sea views. For added privacy, the accommodation features a private entrance. Guests can enjoy the outdoor swimming pool at Hellenga Haven. Key West International Airport is 30 miles from the property.

Child Friendly • Security/Safety • Internet • Laundry • Barbecue/Outdoor Cooking • Pool

On private beach with outdoor pool, near Bahia Honda State Park
At Sunshine Key RV Resort & Marina, hit the private sand beach, relax by an outdoor pool, or spend the day at a marina.
Bathrooms are shared and housekeeping is not available.
Sunshine Key RV Resort & Marina offers 10 air-conditioned accommodations with fireplaces and coffee/tea makers. These individually decorated and furnished accommodations have separate sitting areas and include dining tables and kitchen islands. Kitchens offer refrigerators, stovetops, microwaves, and cookware/dishes/utensils.

Guests have access to shared bathrooms. Bathrooms include showers with rainfall showerheads. Cable television is provided.

- "Love the tropical and nautical ambiance of the resort. The maintenance staff is friendly, helpful, and professional. Love all of the resident wildlife! 3rd visit here, first two in my own rig, wonderful experiences both! Fully 5 star ratings for those stays. I wouldn't give 5 stars for the trailer rental however. All in all, the trailer was adequate, but with the following exceptions: 1. The mattresses were horrible - the foldout sofa "mattress" was unusable and the bedroom "mattress" has a large unavoidable sunken-in crater on each side. 2. The water pressure was almost non-existent. 3. The slide-out by the stove is a major trip hazard and toe-stubber. "

Sunshine Key King Travel Trailer 4 is situated in Big Pine Key. The property is 17 km from Marathon, and complimentary private parking is offered. This air-conditioned holiday home has 1 bedroom, a cable flat-screen TV, and a kitchen with a microwave and a fridge. Towels and bed linen are featured. A children's playground can be found at the holiday home, along with a shared lounge. Cudjoe Key is 26 km from Sunshine Key King Travel Trailer 4, while Duck Key is 37 km from the property. The nearest airport is Key West International Airport, 60 km from the accommodation.

Child Friendly • Parking • Internet • Balcony/Terrace • View • Air Conditioner • Pet Friendly • Laundry • Wheelchair Accessible • Pool • Kitchen • Ocean View

Discover the beauty of Big Pine Key from this delightful 2-bedroom house. With a king bed and a queen bed, guests can relax in comfort. Enjoy the convenience of WiFi, AC, and a washing machine during your stay. The 2 bathrooms are equipped with all of the conveniences of home. Located between the Back Bay and the Ocean. Property sits on an acre lot, enjoy the breezy, shady side porch or the blazing sun on the rear porch while cooking on the Traeger Grill. Modern conveniences close by. Grocery store, lots of Eateries The Famous No Name Restaurant, Forks & Stixs, Boardwalk, Jolly Mon. Bahia Honda just a short ride, The Seven Mile Bridge, The Blue Hole, Horseshoe, Big Pine Key Park, Ramrod Fishing Hole, The Jumping Bridge, Boat Ramps and Key Deer in the yard. Key West, Fort Zachary Taylor, Mallory Square Sunsets only 30 miles away. There is also a RV spot for rent on the property if you bring your RV to accommodate more guests. The Florida Keys 42 Bridges connecting 40 Islands. Paradise

- "The property is secluded and has a nice landscaping around it. The deer in the yard and the daily Egret are fun to watch. The two roosters are beautiful as well." - "The best of Big Pine Key — Key deer right in your backyard! The house was comfy and well equipped. The owner was easy to communicate with. Overall a great stay! Highly recommend!"

A recently renovated apartment, Ocean View Room at Barnacle Resort offers accommodations in Big Pine Key. This beachfront property offers access to a patio and free Wifi. Florida Keys Aquarium Encounters is 22 miles away and Seven Mile Bridge is 15 miles from the apartment. The air-conditioned apartment is composed of 1 separate bedroom, a fully equipped kitchenette with a microwave and a fridge, and 1 bathroom. Towels and bed linen are featured in the apartment. The property offers sea views. Guests can also relax in the garden. Captain Hook S Marina Dive Center is 22 miles from the apartment, while A Deep Blue Dive Center is 22 miles away. Key West International Airport is 32 miles from the property.

- "Amazing stay 😇"

Beautiful, well maintained canal front home at the end of Big Pine Key. Surrounded by the Key Deer National Refuge. Wake up to Key Deer in your back yard. Only 30 miles from Key West and Duval Street. Concrete, step-down dock. Bring your boat. Great fishing and Diving. Bahia Honda Beach close by. Comfortably sleeps 6 plus two full sized sofas in the living room. New hi definition TV's, cable, Wi-Fi. Central air, wrap around deck. The canal leads out to Pine Chanel. Just a short scenic boat ride to the ocean or the Gulf. Lots of uninhabited islands to explore. Rent a kayak and have it delivered to you. Bike rental available as well. Miles of bike paths to explore. The island also has a park with tennis courts, basketball courts and a playground. Explore the Blue Hole on the island. An old rock quarry dug for the Flagler railroad that has turned into a habitat.

- "excellent" - "The two most important things: The property was very clean and the beds were great. We stayed here five years ago and the property was just as nice then as it was before. Absolutely love the location, right next to the Key Deer Preserve, with many deer visitors stopping by to make our day; they are just so beautiful. This is a very quiet neighborhood and we enjoyed sitting outside by the canal in the evenings marveling at the stars, which I never see at home. The property owner was very responsive and easy to deal with. The kitchen was very well stocked with more frying pans than I've ever seen in any rental and many incidentals. Alas, that did not include a mixer, but since I knew the kitchen was well stocked, I didn't even ask and I should have. We love this place and will come back again (and probably again)."

A recently renovated apartment, Ocean Depth Room at Barnacle Resort offers accommodations in Big Pine Key. This beachfront property offers access to a patio and free Wifi. Captain Hook S Marina Dive Center is 22 miles away and A Deep Blue Dive Center is 22 miles from the apartment. The air-conditioned apartment is composed of 1 separate bedroom, a fully equipped kitchenette with a microwave and a fridge, and 1 bathroom. A TV is featured. The property offers sea views. Guests can also relax in the garden. Florida Keys Aquarium Encounters is 22 miles from the apartment, while Seven Mile Bridge is 15 miles away. Key West International Airport is 32 miles from the property.

- "Great location.clean and comfortable room nice beach Only improvement woukd be communication with host"

Please note that we have a 28 day minimum rental period with no subletting. This is a Monroe County Regulation to preserve the beauty and peacefulness of Big Pine Key. PLEASE CLICK VIEW MORE BELOW TO VIEW CANCELLATION POLICY

My property is a rare find in the lower keys. Nestled in the middle of the Key Deer Wildlife Refuge. This house is located 30 miles northeast of Key West. The property consists of three full lots at the tip of Doctor's Arm Peninsula. Please take a look at the aerial photos to see the space you will have during your stay. Don’t forget to bring your camera as Key Deer travel through the property daily. My home has 2 bedrooms 2 baths with one king size bed in the master bedroom , one queen murphy bed in the living room, and two twin beds in the guest bedroom plus a pool and heated downstairs shower. The 50 foot concrete dock is ready for your boat with fish cleaning station and approximately ten feet depth. Cable TV , Netflix, and WIFI is included. There are TVs in each bedroom and living room. The kitchen is fully equipped for cooking and there are plenty of towels.

>Convenient to grocery store, restaurants, and local bars (walking distance to No Name Pub)
>A short drive to Bahia Honda State Park, Key West, and Marathon.
>Boat Ramps nearby at Old Wooden Bridge Marina and Bahia Honda State Park
>Plenty of room to store your boat trailer on the property

REFUND POLICY: 120 Days before your reservation you will receive 100% of your payment refunded And 60 Days before your reservation 50% Of your payment will be refunded (this does not include the VRBO service fee). If a mandatory evacuation is ordered, your stay will be pro-rated at a daily rate of base rent only(does not include vrbo service fees, tax, cleaning, fees, etc.) Please do not hesitate to contact with any questions.

- "We had another year where we felt like we were staying in the keys before it got so built up. This property is not a fancy resort but is an even more beautiful old Keys atmosphere and perfect for our boat, fishing, relaxing, and enjoying time with family. Communication with property owner is always great and very personal. We will definitely be staying again next year." - "We love the natural setting. Big private environment. Very quiet and secluded with everything you need to be comfortable. The owners are very responsive and quick to address any needs. We have been coming for several years and always love it and hate to leave. Cletha and Neil"

A recently renovated vacation home, Treehouse Private Village at Barnacle Resort offers accommodations in Big Pine Key. Both free Wifi and parking on-site are accessible at the vacation home free of charge. Florida Keys Aquarium Encounters is 22 miles from the vacation home and Seven Mile Bridge is 15 miles away. The spacious vacation home has 1 bedroom and 1 bathroom with a hair dryer. Towels and bed linen are offered in the vacation home. For added privacy, the accommodation features a private entrance. Guests can relax in the garden at the property. Captain Hook S Marina Dive Center is 22 miles from Treehouse Private Village at Barnacle Resort, while A Deep Blue Dive Center is 22 miles from the property. Key West International Airport is 32 miles away.

Security/Safety • Ev Charge Station • Parking • Air Conditioner • Internet • Pet Friendly • View

Terrific Key getaway for rent!! Newly remodeled 2 Bedroom 2 full bath canal front home with 50 feet of dock. Located in desirable Doctor's Arm neighborhood, this house is just around the corner from the famous No Name Pub on Big Pine Key. Quick idle to Spanish Harbor Channel and easy access to the ocean or the gulf. Less than a mile from the No Name Bridge, so there is access to fantastic fishing within walking distance even if you don't have a boat!! The house is a short drive to Bahia Honda State Park, and a short boat ride to Looe Key, world class snorkeling and diving. 30 miles to Key West if you choose a night out on the town!! Two tandem kayaks and two bikes available with rental.

Large Master Bedroom has 1 King Bed and a walk in closet.
2nd Bedroom has Full over Full Bunks and XL Twin over XL Twin Bunks.
Washer and Dryer
Internet/Cable Roku TV
Kitchen Table seats 6
Propane Grill
2 Tandem Kayaks
2 Bicycles
Bait Freezer Downstairs
Filet Table

- "This rental is perfect for both anglers and animal lovers, and there's no need to cross the bridge and deal with the traffic to get groceries, bait, ice, or fuel. All necessities are right there in Big Pine Key. Val and Nicole were incredibly generous. They invited us to join them on their boat for the day, and my husband and son had a great time. I loved watching the deer, birds, and manatees; Big Pine Key is full of life! We also visited the Laura Quinn Wild Bird Sanctuary in Tavernier and the Turtle Hospital in Marathon. We all had a fantastic holiday. Thank you, Val and Nicole!!"

A recently renovated apartment, Star Room at Barnacle Resort offers accommodations in Big Pine Key. Both free Wifi and parking on-site are accessible at the apartment free of charge. Captain Hook S Marina Dive Center is 22 miles from the apartment and A Deep Blue Dive Center is 22 miles away. The air-conditioned apartment is composed of 1 separate bedroom, a living room, a fully equipped kitchenette with a microwave and fridge, and 1 bathroom. Towels and bed linen are available in the apartment. Guests can relax in the garden at the property. Florida Keys Aquarium Encounters is 22 miles from Star Room at Barnacle Resort, while Seven Mile Bridge is 15 miles from the property. Key West International Airport is 32 miles away.

Ocean View • Parking • Air Conditioner • Internet • Pet Friendly • Oceanfront • Security/Safety • View

LARGE 3 BEDROOM HOUSE LOCATED NEAR ALL THE ACTION!! ONLY 3 MILES FROM BAHIA HONDA BEACH PARK, AND 26 MILES FROM KEY WEST, HOUSE IS VERY SPACIOUS GREAT FOR LARGE FAMILIES, IT ALSO OFFERS PLENTY OF SPACE FOR BOAT TRAILER AND ALL YOUR WATER TOYS.

HOUSE IS LOCATED 29 MILES FROM KEY WEST INTERNATIONAL AIRPORT AND A SHORT DRIVE TO DOWN TOWN KEY WEST, HOUSE IS LOCATED IN THE HEART OF KEY DEER SANCTUARY OFFERING OUR GUESTS THE ONCE IN A LIFETIME OPPORTUNITY TO SEE OUR BEAUTIFUL KEY DEERS.

Child Friendly • Balcony/Terrace • Air Conditioner • Laundry • Child Friendly • Internet • Kitchen • Bedding/Linens

Deer Run on the Atlantic in Big Pine Key provides adults-only accommodations with a private beach area, water sports facilities, and free bikes. This beachfront property offers access to darts, free private parking, and free Wifi. The bed and breakfast offers a hot tub and full-day security. The bed and breakfast features some units with sea views, and every unit is equipped with a private bathroom. There is an on-site coffee shop. Guests at the bed and breakfast can enjoy cycling and hiking nearby, or make the most of the sun terrace. Florida Keys Aquarium Encounters is 22 miles from Deer Run on the Atlantic, while Seven Mile Bridge is 16 miles away. Key West International Airport is 32 miles from the property, and the property offers a paid airport shuttle service.

Fireplace/Heating • Air Conditioner • Security/Safety • Guest Services • Pet Friendly • View • Transportation/Shuttle • Hot Tub • Entertainment • Ocean View • Parking • Breakfast

Excellent location 2 bedroom 2 bath home with a 65 ft sea wall on wide canal in Big Pine Key. This is a perfect location for boaters. A marina with fuel docks is located at the end of the canal. Hopefully you won’t need it, but Boat U.S. is across the canal. The canal is the very easy to navigate and less than a 5 minute cruise to the channel. A tackle store is at the end of the street.

Outdoor amenities include a locked downstairs storage room, large bait freezer, fish cleaning table and more! Also included are a brand new gas grill, a charcoal grill, 3 kayaks, 2 paddleboards, 3 bicycles and water toys. There is plenty of parking for vehicles and a boat trailer. The location is very convenient with a fuel dock at the end of the and a tackle store just a few houses down from the house. Shopping and restaurants are a short bike ride away.

The interior has many windows for views of the canal and is freshly painted. The open floor plan creates a great space for conversation and traffic flow. There are two bedroom suites, one with a queen bed and the other with two double beds. The kitchen appliances are new as is the cookware and dining ware. The living room furniture is very comfortable. The dining table has six seats but is large enough to accompany a couple more and is a great place to play the included board games or puzzles.

The house has two screened porches. The upstairs porch wraps from one side of the across the entire back of the house and is a great place for sunset views. The downstairs screened porch has an additional dining table. There is also an outdoor shower. The enclosed area downstairs has a second refrigerator, a bait freezer, washer and dryer and plenty of storage.

28 day minimum rental per Monroe County code.
Please contact me with any questions.

- "The listing was accurate, nice neighborhood, great places very close by." - "Michelle(owner) was very responsive to all are our inquiries and requests. She had very good restaurants and attractions to recommend and visit. She has kayaks and bicycles for roaming around Big Pine. Her neighbors are very friendly. It was a relaxing and fun time" - "Nice quiet neighborhood, fun canal for swimming, kayaking, watching all the boats and the manatees. We enjoyed our morning walks with our dog to Pine Channel Park to watch the sunrise from the viewing platform. Michelle is a great host. Anne from Minnesota"