Charming Cottages in Clearwater, FL

Jupiter Pines Cottage is located in Clearwater, just 3 miles from Pier 60 and 15 miles from John's Pass. The vacation home has access to a restaurant. The vacation home also offers facilities for disabled guests. The air-conditioned vacation home consists of 3 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 offered in the vacation home. For added privacy, the accommodation features a private entrance. John's Pass Village and Boardwalk is 15 miles from the vacation home, while Raymond James Stadium is 18 miles from the property. St. Pete-Clearwater International Airport is 8.7 miles away.

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

Escape to this very private cottage recently completely renovated and newly furnished. The home is about 1 mile to charming downtown Dunedin. One bedroom one bath home 3 blocks from the gulf and 2 houses from the Pinellas Trail. Located in Clearwater just 4 blocks from the Dunedin border. Very private home located in the far back of an otherwise empty double lot. Fieldstone fireplace see thru from living room to bedroom. Private fenced in yard off the living room with sliding door access. Brand new kitchen and bath with new appliances just installed. Recessed lighting throughout with A/C, washer/dryer and garbage disposal. Ride your bike or walk into downtown Dunedin. The calendar is open for this Season.

- "Stayed in town for 6 weeks. Couldn’t have had a better experience at the cottage. Property manager was very accessible and quick to respond to any questions. The property was wonderfully quiet and clean and well done. 10/10 recommend and would stay there again! "

Take it easy at this unique and tranquil getaway in our Historic 1920’s Clearwater cottage. The location is ideal for a weekend getaway or a few weeks stay. We are conveniently located 8-10 minutes from Clearwater Beach and approx. 30 minutes from the TPA Airport. The Clearwater Cottage is one of the original homes built 5 yrs after Clearwater was established in 1915 and has been updated providing everything you need during your stay. We look forward to hosting you, your friends, and/or family!

- "5/5 offers exactly what is posted. AC was alittle inconsistent but other than that lovely quaint property." - "Property clean and comfortable for a group of 6 people. House is located closed to the beach , shopping centers and pharmacies. The Neighborhood is very quiet and property has a good space for parking. Vicky is a very good host and always responded to my texts or phone calls when I had questions. I recommend this house for a family or friends getaway weekend."

This is a studio cottage that sits nestled under an amazing 150 yr old live oak. It's very private and has it's own driveway that will fit 2 cars.
Earth friendly and affordable " The Cottage" has a cozy atmosphere. It has everything you need for long week get aways. But book longer, you wont want to leave. Situated near many must see and do attractions, you wont have to go far to stay entertained.

The kitchen has a stove, refrigerator, double sink, microwave, toaster, coffee maker, cookware, dishes, basic seasonings, paper towels & dish soap. There is a shared gas grill on the fire pit patio.

The bathroom has a ceramic tiled, walk in shower. An ample supply of towels and complimentary basket of toiletries. If you need fresh towels please call the office fora fresh batch.

Travel light--The cottage comes with blow dryer, iron, beach towels, 2 beach chairs and an umbrella.

In room entertainment--Streaming media, Netflix, DVD, WIFI, board games (in the laundry room).

I am committed to environmental sustainability. We implement composting, recycling, up-cycling, rain water harvesting, soil restorations whenever possible.
The gardens behind the cottage are a certified wildlife habitat. We are home to the endangered Monarch butterfly as well as native birds and plants.

Details:

Bed -Queen size with 4 allergen free bamboo pillows.

Pet Friendly-Don't leave Pumpkin home with a sitter!

Private driveway that accommodates 2 cars. Bonus: You can pull right up to the front door for easy baggage loading.

Onsite management- I am a long time resident of Clearwater and I am happy to give recommendations on where to go and how to get there. I always respect your privacy in the event that you need something please call or stop by our office. Guests staying longer than 14 days will receive complimentary housekeeping bi-monthly by my staff.

Onsite laundry room- Pay per use $3 a load when you use your own laundry products. $4 if you use ours.

No charge for extra person. Air mattress & pack and play is available for use upon request.

Beaches:
Clearwater beach- Voted #1 city beach in the country! It's got it all--Restaurants bars, shopping and 3 miles of pure, white, sandy beaches. Nightly Sunset Festival on Pier 60 4:00-8:00 pm weather permitting. Free movies on the beach Friday & Saturday nights. It's short 4.7 miles -drive, bike or take the bus.

Honeymoon island state park beach-voted top 10 beach in the country. Nature lovers will find osprey nests, a wide variety of shorebirds, and one of the few remaining virgin slash pine forests in south Florida. The park boasts several nature trails and bird observation areas. Visitors can swim, fish, and snorkel in the warm waters of the gulf or picnic while they enjoy the beautiful scenery. Shelling is particularly good here, as the gulf currents deposit an incredible variety of seashells on the shore. Showers are available and the park´s concession has a gift shop and snack bar. 7.3 miles-drive, bike or take the bus.

Caladesi Island-it is one of the few completely natural islands along Florida´s gulf coast, Caladesi´s white sand beaches were rated america's best beach in 2008. Beach lovers can enjoy swimming, sunbathing and beach combing. Saltwater anglers can cast a line from their boats or surf fish. Nature enthusiasts can spot wildlife while hiking the three mile nature trail through the island´s interior or paddling a three mile kayak trail through the mangroves and bay. Picnic tables and shelters are located near the beach. Take the ferry from honeymoon island.

Other fun stuff-
Delightful downtown Dunedin-quaint, funky, trendy vibe. (20 minute walk) pubs, cafes, shopping & local art. Have dinner at one of the restaurants (you won't find any chain restaurants here and all of them are great. Then party all night at the blur nightclub or have martini's at the chic-a-boom room. Wander on home then go back in the morning for the Saturday morning market or Kelly's amazing Sunday brunch, take a walk on the trail or shop for unique art, wine, fashion or chocolates--there is always something happening here!

Pinellas trail: 25 miles of biking, blading, walking trail with plenty of neat places to stop along the way.

Dunedin brewery: the oldest microbrewery in Florida. Live band thurs-fri. (20 min walk )

Blue jays stadium-ball game anyone? (15 min walk)
Dunedin is very bicycle friendly!

Tarpon springs sponge docks- visit our Greek village. Greek food, belly dancing, sponge diving, unique shops, euro style cafes, bakeries, hand made soaps and more.

- "Very clean and inviting cottage, feels pleasingly comfortable. The garden and yard makes me feel happy and relaxed. Vicki seems like an old friend. Great information about area in room, from thrift stores to dog parks. I have recommended it to several people at work already." - "The garden was whimsical and charming. Vickie was kind. The cottage was close to the beach" - "The cottage is exactly as advertised, small but has everything one would need to live comfortably. It's probably 10x15 total, but use of space is great, still space to move around and store a few things. I'd come back in a minute."

Come stay in our safe and quiet little backyard house that was opened in early 2023. Make a cup of coffee or a complete meal in the fully-equipped kitchen! Use our front house porch or garden bench to sit by the lake and relax.
Sit on the private back patio and enjoy the sun. Very rural setting near the end of a dead-end road. Listen to the birds singing! Enjoy the ducks, turtles and other gifts of Nature. Sometimes we hear owls at night. Walk a few blocks to a small park with a creek. Very beautiful and peaceful. Close to Clearwater Beach, Dunedin and Safety Harbor.

- "This backyard sanctuary quickly became our home away from home during the 6 weeks we were here. We loved everything about this place: the quiet setting by the lake and under the old oak trees, the amenities and furnishings, and the covered parking! Our hostess' attention to detail was evident in everything from the themed towels to the pretty wall decorations and the well-stocked kitchen. We especially loved the organic coffee and snacks! The location was central to all places and people we wanted to visit. Leslie was the perfect hostess, quickly responding to all our needs. In short, it was perfect and helped make our stay in Pinellas special."

Discover the beautiful butterfly murals that adorn this cozy tiny home nestled conveniently between Clearwater Beach and Honeymoon Island. This private studio offers all the vacation essentials for a seamless escape. Enjoy a full kitchen, a private outdoor patio, and a queen-size bed, complete with a smart TV, high-speed wifi, private parking, and keyless entry.

Feel at home with a full-size fridge, an oven, and all the basic cooking essentials provided. Complimentary Netflix, beach gear (cooler, towels, chair, umbrella), and bikes make your stay even more enjoyable. The nearby Pinellas Trail leads you to Dunedin, a charming town filled with breweries, dining, shopping, and live entertainment.

Just a short 15-minute drive away, immerse yourself in the beautiful beaches. This tiny home isn't just a place to stay—it's an invitation to experience the best of the area. This is part of a duplex unit with private entrance and private fenced yard. Please inquire if you’re interested in renting the whole property.

- "It is close to dunedin ballpark and market. Walking distance to gulf." - "The property was perfect! Very clean and totally equipped with anything you could need for your stay! Very cute and comfortable! The property manager was very kind and willing to help if we had any issues. We definitely recommend this property and would book again!" - "Had a great stay in Dunedin - rode the Pinellas Trail on our bicycles, enjoyed the water and local restaurants. Great location! Cute, clean accommodations."

This beautiful little cottage has a very open concept it’ll sleep six guest and has two bedrooms one bathroom and a outdoor shower, just 8mnts from the beach of Clearwater and close to to downtown and Dunedin as well this house is perfectly located for you to experience old style Florida beach vacation restaurants and bars close by where you can take the family and make the best of your time of your vacation.

- "Veronica was an awesome host, very responsive." - "Just what we needed. Quiet and we all slept probably the best ever each night. Close to a nice park to run with the dog or play tennis. Lots of birds in that park including parrots. Maybe not the best neighborhood near the park but everyone was nice and well behaved. Quick drive to the beach. Forgot houses in Florida often have an outdoor shower, so was happy to see that and used it for most of my showers. Porch was a nice place to sit in the back and have a beer. Didn't use the front porch but the neighbors were nice."

Welcome to this newly remodeled, stylish and modern cottage that offers the perfect getaway experience, designed to help you soak up all the charm and beauty of the local area.

This stunning property boasts two beautiful bedrooms, an extra sleeping space, and a brand new designer kitchen and bath, giving you all the space and luxury you need to relax and unwind. Outside, enjoy the the full deck with firepit and patio, where you can bask in the sunshine, read a book, or grill your evening meal.

Located just 5 minutes from Causeway Beach and 7 miles from the world-famous Clearwater Beach, this property is also conveniently close to downtown Safety Harbor and Dunedin, which offer an abundance of shops and restaurants to explore. And for sports fans, it's just a short drive to Tampa and Bucs games. Don't miss out on the opportunity to experience the ultimate in vacation luxury - book your stay today!

- "A lovely home, so nicely decorated and stocked with everything a visitor could need. We enjoyed our stay tremendously and would gladly return. Peter and Lisa are great hosts, although we had little to ask for as they had anticipated most of our needs. The neighborhood is quiet and convenient to both the beaches and to activities in Tampa. Thanks for a great visit." - "Easy check in / out and communication, pristine place for a pleasant and peaceful stay."

This is our rustic cottage guest house. It is behind its own private gate, and has its own private yard. The driveway and laundry room are shared with the main house. Everything else is private. It has off-street parking for two cars and a fire pit in the yard.
There is a large living room, dining room with a full kitchenette and a new 55" TV with many streaming channels. The bedroom has a cedar closet. The entire cottage was just renovated and it's a spacious and comfortable space with high ceilings in the main room. The large communal pool is five doors down in our back yard and accessable any time.

- "I met Mike the owner upon arrival. Check in was quick and easy. Mike checked in with me after I was there a day or two, to be sure all was well. Everything I needed was provided. My experience was a good one. Thanks. Dan T."

Have fun with the whole family at this private luxury 1 bedroom house called the Mango Tree cottage, named after the large mango tree that sits beside it. This 1 bedroom spacious cottage has a comfortable Queen size bed, a sleeper sofa, and a private patio. Your private patio comes with a grill and lounge area. Full sized kitchen includes everything you may need. Access to full size washer dryer upon request. Your cottage even includes bicycles with direct access to the Pinellas trail that will take you downtown Dunedin or downtown Clearwater.

Free personal parking space. Enter the living room with a peloton treadmill and a big screen smart tv. Large kitchen/lounge area with pull out sofa. 1 bedroom with queen bed and 1 bathroom with bath/shower. Has a back door to private patio. Back gate leads to the pinellas trail. We are a 7min bike ride (1.4 miles) to the Fenway hotel, and an 8min bike ride (1.5miles) to Main Street, downtown Dunedin. 12min bike ride (2.1miles) to Cleveland street, downtown Clearwater. Downtown Dunedin has delicious eats and quaint little shops.

- "This cottage was exactly as pictured and delivered the ideal retreat with easy access to amenities and activities.Its proximity to the rail trail made walking or riding for coffee/dinners easy, and Sam provides two bikes with locks for excursions.The cottage is beautifully tucked away amid a variety of trees and plants.Sam thoughtfully included several coffee/hot chocolate options for the Keurig and even left us some delish pastries on check-in day! The kitchen was equipped with all the necessary pots/pans/utensils to cook any meal type.The bed was hotel quality, affording fantastic sleep/naps.Parking was ample and well-protected.Wi-fi was very reliable.This would be an ideal stay for a Blue Jays fan taking in Grapefruit/spring games as the stadium is within walking-riding distance.Fave cafe nearby: Tükrō Coffee ShopFave parking spot for Clearwater Beach strolls: Lot 37 Avalon Kendall"

A very cozy and private detached guest house in a quiet neighborhood in Clearwater. The backyard is fenced in and very private.
There is no TV in this listing, but there is high speed wifi and a small collection of various books

Other • Parking • Wellness Facilities • Child Friendly • Bedding/Linens • Kitchen • Smoking • Air Conditioner • Laundry • Internet • Pet Friendly

Experience white sand beaches, clear blue waters, and stunning sunsets at this lovely 1-bathroom studio! Perfect for a romantic couples retreat or a spontaneous solo trip, this vacation rental features a comfortable interior, zen-inspired décor, and a private outdoor space for relaxing. When you’re not lounging at home, catch a baseball game at Spectrum Field or play a round of miniature golf at Congo River Golf. Don’t forget to pack your sunscreen so you can soak up the sun at Clearwater Beach!

-- THE PROPERTY --

Step-Free Access | In-Unit Laundry | Fenced-In Studio

Studio: Queen Bed

MAIN FEATURES: Private outdoor lounge w/ water feature & garden, zen meditation decor, one-of-a-kind artwork, books
KITCHEN: Cooking basics, refrigerator, microwave, stove/oven, dishware & flatware, 12-cup drip coffee maker (starter coffee & filters provided)
GENERAL: Free WiFi, central A/C & heating, towels/linens, hangers, trash bags/paper towels, complimentary toiletries
FAQ: Homeowner on-site, 1 exterior security camera (facing the driveway)
PARKING: Shared driveway (1 vehicle)

-- THE LOCATION --

BEACHES: Pier 60 Park (4.9 miles), Clearwater Beach (5.1 miles), Honeymoon Island State Park (6.3 miles), Sand Key Park (6.7 miles), Caladesi Island State Park (7.1 miles), North Beach (8.0 miles)
DUNEDIN (1.5 miles): Shopping, restaurants, parks, beaches, biking & walking trails, boat tours
FAMILY FUN: Celebration Station (4.1 miles), Clearwater Marine Aquarium (4.4 miles), Whimzeyland (5.7 miles), Congo River Golf (6.1 miles), Florida Botanical Gardens (9.7 miles)
OUTDOOR ACTIVITIES: Coachman Park (2.5 miles), Clearwater Beach Municipal Marina (4.9 miles), Largo Central Park (6.3 miles), Philippe Park (8.6 miles), John Chesnut Senior Park (11.5 miles)
THINGS TO DO: Toronto Blue Jays stadium (0.5 miles), Spectrum Field (5.3 miles), Pier 60 (6.0 miles), Ruth Eckerd Hall (6.4 miles), Tampa Bay Downs (12.0 miles)
TAMPA: Tampa Riverwalk (24.2 miles), The Florida Aquarium (25.4 miles), ZooTampa at Lowry Park (28.5 miles), Busch Gardens Tampa Bay (32.0 miles), Adventure Island (32.2 miles)
AIRPORTS: St. Pete–Clearwater International Airport (11.5 miles), Tampa International Airport (19.2 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome--because we know what vacation means to you.

-- POLICIES --

- No smoking or vaping of any kind
- No pets allowed
- No events, parties, or large gatherings
- Must be at least 25 years old to book
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: The homeowner lives in the main house on-site, in a separate unit with a separate entrance, and may be present during your stay
- NOTE: Your safety matters. This property features 1 exterior security camera located above the front door, facing outward toward the driveway. It does not look into any interior spaces. The camera records video and sound when activated by motion. It will record when it first senses motion and 30 seconds after the last motion is detected

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

Separate, side entrance. Bungalow behind main house. Separate building. Pets welcome. Comfortable one bedroom w/ additional sleeper sofa in living room. Full kitchen. Washer/Dryer. Central A/C. WIFI speed > 500 mbps. Off road parking. Less that 1/2 mile to Pinellas Trail: old train bed converted into walking/biking trail connecting entire county. Les than 1/2 mile to Blue Jays Stadium. 1.5 miles from downtown Dunedin: Main Street town, tourist destination (shopping, dining). 2.4 miles from LifeWorks Wellness Center. Within 2 miles of Clearwater Beach Causeway: causeway out to island where Clearwater Beach is. Location is residential and quiet. Real Florida experience.

Internet • Kitchen • Other • Air Conditioner • Tv • Laundry • Fireplace/Heating • Smoking • Pet Friendly • Wellness Facilities • Parking • Bedding/Linens

Make your vacation relaxing, fun and easy!
- Kick back in the hammock or have some coffee with loved ones in the peaceful private backyard.
- Head to the beach with the provided boogie boards, chairs and sand toys.
- Take a walk or bike ride on the gorgeous Pinellas Trail. You'll also find some of the best coffee, food and ice cream on the way.
-Golf courses close by.

This is a separate unit that shares a driveway and parking area with the front house.

Child Friendly

This is our guest house, it is about 400 square feet, was fully renovated 2 years ago. There is a large swimming pool , off street parking, very high speed internet and cable TV. There is a new Stearns and Foster queen size bed, and a single bed.

Air conditioning • Hair dryer • Washer • Hot water • Essentials • Heating • Hangers • TV • Dryer • Shampoo

Your family will be close to everything when you stay at this centrally-located place. just 6.9 from Clearwater International Airport , 1.7 miles from downtown where you can enjoy the farmer’s market, shopping centers, restaurants, bars, and much more 3.5 miles from beautiful beaches, 1.1 miles from intercostal downtown Clearwater, only 2.8 miles from the Marine Aquarium and much more to make your vacation full of great memories and a lot to enjoy.

Other things to note
We have a permanent resident (a couple) in their motorhome in the backyard. There’s a fence in between the house and the back yard for your privacy and also a gate to give you the access to the outdoor shower.

Hair dryer • Clothing storage: closet and dresser • Extra pillows and blankets • Cleaning products • Outdoor shower • Hangers • Ethernet connection • Essentials • Hot water • TV

Sleeps 4 comfortably w/ a queen bed in the master & 2 pull out full size couches with a beautiful large bathroom, 9’ ceilings, and an open floor plan! This cottage is the perfect place to spend your Florida vacation! The backyard space is stunning & features fountains, a fire pit, a grill, seating and you can walk or bike out of the back gate of the property right onto the Pinellas Trail or walk to the waters of the Gulf of Mexico! Check out our YouTube video The Pink Pearl Cottage on the Trail!

The space
We are located centrally to all of the fun in Tampa Bay! Just a 5 minute bike ride to Downtown Dunedin which has many shops, breweries and some of the BEST restaurants in Tampa Bay! Only a 25 minute bike ride to Honeymoon Island and 25 min bike ride to Clearwater Beach! Our beautiful 1925 Pink Pearl Cottage located on The Pinellas Trail in Clearwater/the Greater Dunedin area of Florida is a place that you will want to vacation and return to time and time again! We had a dream of turning our magical 1925 Cottage into a place that people would want to enjoy. We want our guests to feel that they are in a magical place frozen in time. This dream cottage sleeps 4 guests and is 1,100 sq feet of heated and cooled space with over 1,000 sq feet of exterior patio and outdoor deck space for your enjoyment. This amazing property is available for guests year round and comes with everything that you would need to make your stay most enjoyable. We also take pride in the cleanliness of our property. This is an extremely important part of making sure your stay is nothing but the best. You can walk or bike out of the back gate of the property right onto the Pinellas Trail. Just a short walk or ride north and you will find yourself in Downtown Dunedin and just a 2 minute walk south you will find yourself overlooking the Stevenson Creek Bridge which leads out to the Gulf. Feel free to fish or just enjoy nature off of this bridge. Also if you walk west just a few blocks on Sunset Point Road you will end at Edgewater Drive where you can watch the most incredible sunsets. There is a kayak launch at the end of the street that will take you and your kayak right out to the intercoastal waterway. The property includes 2 stunning fountains, a large shaded deck, a gas fire pit, a gas grill, original brick walkways, paved patio spaces, shell pathways and beautiful gardens. Enjoy the sounds of water, birds and nature with a constant sea breeze while lounging under a large oak tree. This property is perfect for a couples romantic getaway, world or business traveler or a small family! This 1925 Cottage has soaring 9' ceilings, original 8" baseboard trim, original window casing and door trim. 2 fountains, a large deck overlooking the magical backyard oasis, a propane grill and propane fire pit with seating on the decks, rocking chairs on the shell firepit area and a 4 person table with umbrella on the brick patio. We also have a tandem (2 person) bike for you to use during your stay! Plenty of parking and if you would like to bring your boat you can park it right in the driveway and launch it at Seminole boat launch which is only a 4 minute drive away! We hope you book with us and enjoy a magical vacation!
Warmest Wishes, Katie & Dax

Body soap • Conditioner • Hot water • Washer • Garden view • Shampoo • Hangers • Free dryer – In unit • Essentials • Hair dryer