Vacation rentals with a pool in Wakulla County

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Top-rated rentals with a pool in Wakulla County

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Guest favorite
The exterior of a one-story residential home is shown, featuring a covered porch and a manicured lawn. Lush greenery and palm trees frame the property, while a clear blue sky is visible above, suggesting a bright and sunny day.
Home in Crawfordville
4.81 out of 5 average rating, 16 reviews

Blue Heron House

This lovely river front one story 3 bedroom, 2 bathroom home is located within the private gated community of Paradise Village. Our home sleeps 6 comfortably. Prepare your morning coffee and enjoy a peaceful start to your day on the fishing dock! Outdoor enthusiasts love taking their boat out for fishing, while fitness mavens enjoy the tennis facilities and jogging through the calm streets of Shell Point. As the sun sets, guests like to prepare delicious family dinners on our outdoor grill. Try to spot a shooting star beneath the sparkling night sky that this area offers! In case of a rainy day, we have prepared board games and puzzles to keep your family occupied! And what’s better than a cup of hot chocolate, a big throw blanket and your favorite show? Enjoy a family movie night with our smart TV with Internet and streaming capabilities! All pillows, linens, towels and cozy throw blankets are provided. The kitchen is fully supplied with cookware, bake-ware, small appliances, a microwave, and dishwasher. Washer and dryer are also available to our guests. Things to do around Shell Point: For the curious - Enjoy a day of windsurfing, sailing or kayaking alongside our community! Whether you like birdwatching or dolphin watching, there is something for everyone on this coast! Our house is also very close to St. Marks National Wildlife Refuge, as well as Wakulla Springs! For the sports enthusiasts - Challenge your friends to a tennis battle on our tennis courts on site! For the guys - Bring your own boat and enjoy a well-deserved day of fishing with your buddies with direct access to the Gulf! For the ladies - Stretch yourself out on the warm beach of Shell Point, enjoy the cool ocean breeze, and make sure you take in one of our serene sunsets, while collecting beautiful seashells! Damage Deposit Policy: A pre-authorization of USD 500.00 is due 1 days before arrival and released 5 days after departure Pool opens around Easter and closes in October! POOL OPEN HOURS: 30 minutes after sunrise to 30 minutes before sunset ~ $25 Pet fee per stay: Please let us know if you are bringing your pup with you!

Top guest favorite
The coastal home features a two-story structure with a welcoming front porch adorned with wooden railings. The exterior showcases a blend of light and dark shades, framed by lush greenery and tall pine trees. The landscaped yard presents tropical plants and a sandy path leading to the entrance.
Home in Saint Teresa
5.0 out of 5 average rating, 32 reviews

Flip Floppin' - Steps to Beach & Resort Style Pool

Welcome to Flip Floppin' your dream coastal getaway on the Forgotten Coast! This stunning, meticulously designed home combines modern luxury with beach charm and is just steps from the pristine sands of Summer Camp Beach in St. Teresa, FL. The spacious home features a king-sized master bedroom, 2 queen-sized guest suites, along with 2.5 modern bathrooms, all designed with coastal elegance in mind. Book now for a peaceful escape and experience the tranquility of Florida’s Forgotten Coast!

Guest favorite
A serene view of a canal at sunset is captured, with gentle hues of orange and yellow illuminating the sky. Docked boats line the water's edge, and palms sway softly in the foreground, enhancing the natural beauty of the peaceful environment.
Home in Crawfordville
4.93 out of 5 average rating, 81 reviews

Reel Pelican Paradise located in Paradise Village.

Beautiful 3 BR 2 BA well maintained home on a canal that leads to the beautiful Gulf of Mexico. This fully-updated home has a view down the entire canal and a very large screened-in porch. Boat slip is included which accommodates up to a 22' boat. Once you step inside you will love the fabulous layout that includes a separate office and laundry room. The kitchen has custom cabinets, stainless steel appliances and is very well stocked. Tennis courts available as well as pickle ball courts.

Top guest favorite
A cozy living area features a long wooden table with stools, illuminated by soft lamp light. Comfortable chairs are positioned near large windows that provide a view of the water and sunset. A television offers entertainment options for guests.
Home in Panacea
5.0 out of 5 average rating, 23 reviews

OUR REEL DREAM bayfront home

Ochlockonee Bay, private dock, fishing, boating, relaxing. OUR REEL DREAM, on the Forgotten Coast, is the waterfront home that will delight. Nearly 3000 sq ft plus screened lanai & POOL. Walk-in showers & a jetted tub. Cook’s kitchen with new appliances and laundry room. Main home sleeps 8 comfortably. No stairs. Extra parking. If available, cottage has full kitchen, 1 BD, a sleeper sofa & 1.5 BA. Cottage rents only as add-on with main house. Amazing sunsets! Any questions? Just ask!

Guest favorite
A modern home is presented with a light grey exterior and wide porch. A covered area offers sheltered seating, and the driveway features a gravel surface. Surrounding greenery complements the inviting facade, with a hint of blue from the porch overhang against a clear sky.
Home in Saint Teresa
4.93 out of 5 average rating, 44 reviews

Starry Night: 3,800sqft sleeps 18! Pool and Beach!

This is a brand new home in the Summercamp Beach community. It includes access to the resort-style clubhouse and pool, as well as two miles of private beach on the Gulf of Mexico. It’s the perfect spot to unwind and relax. This home is dog friendly! The pet fee covers a deep cleaning required after any pets to ensure maximum cleanliness for the next guest. Please respect local leash laws, but feel free to bring your furry friend to the pet friendly beach. A maximum of two dogs allowed.

Guest favorite
Condo in Carrabelle
5.0 out of 5 average rating, 6 reviews

Where the Boat Leaves From

Riverview Condo at Pirates Landing | Pool, Boat Access & Coastal Getaway Relax and unwind at this charming 1-bedroom, 2-bath condo in Pirates Landing, perfectly situated along the Carrabelle River. Ideal for couples, small families, or a fishing retreat, this fully furnished unit offers comfort, convenience, and a true coastal feel. Enjoy mornings on the screened porch overlooking the river, and evenings with peaceful water views and coastal breezes.

Top guest favorite
The spacious bedroom features a large bed with light bedding, complemented by decorative pillows. A dresser and side tables provide storage, while a ceiling fan adds comfort. Large windows allow natural light, and a cozy seating area can be seen in the background.
Condo in Panacea
4.93 out of 5 average rating, 57 reviews

Bliss on the Bay

Ochlocknee Bay front condo located in George's Lighthouse gated community in beautiful Panacea, Florida. Enjoy beautiful sunset views from the patio, great fishing, biking and kayaking. Walk to community pool, tennis court and the famous Angelo’s Restaurant. Take a short scenic bike ride to Mashes Sands Beach or a short car ride to several Forgotten Coast beaches. St George Island is 1 Hour away. Bike/walking trails all around the area.

Guest favorite
Home in Panacea
5.0 out of 5 average rating, 43 reviews

Coastal Cottage

A nature lover’s paradise, the Coastal Cottage has it all!  Nestled on the edge of Dickerson Bay, it's located in a gated community with a pool, a pool house, a gazebo and a fishing pier. This stylish circular-shaped home comes with an open floor plan, lots of windows and natural light, many new upgrades, and the views are absolutely phenomenal! The home is within walking distance to waterfront restaurants and the Gulf Specimen Aquarium.

Top guest favorite
The exterior of a two-story house showcases a blend of light and dark siding, framed by a gravel driveway and landscaped greenery. A welcoming porch with railing and ceiling fans is visible, along with windows allowing natural light to enter the home.
Home in Saint Teresa
5.0 out of 5 average rating, 26 reviews

Family Tree - Monthly Rates Available

Located on the tranquil shores of St. Teresa along Florida's forgotten coast, "Family Tree" awaits your visit. If you seek a secluded getaway with a serene beach, your stay here will be a true delight. Here you'll discover a wide range of activities and attractions, catering to those interested in fishing, boating, kayaking, golfing, hiking, shopping or simply savoring the coastline. This region truly offers something for everyone.

Top guest favorite
The exterior features a white cottage with a metal roof, surrounded by palm trees. A clear pool is situated in the foreground, accompanied by several lounge chairs. Large windows line the front, providing ample natural light to the inviting living spaces.
Home in Panacea
5.0 out of 5 average rating, 45 reviews

NEW Florida Coastal Cottage with Pool and Dock

This newly constructed Florida coastal cottage is a dream getaway for nature enthusiasts and anglers alike. This charming 4-bedroom, 2.5-bathroom home accommodates up to 8 guests. With the new addition of a pool, its partial water view and proximity to local beaches, it truly offers the best of both worlds for relaxation and adventure. Enjoy the view from a newly constructed dock, shared with two other homes.

Top guest favorite
Home in Carrabelle
5.0 out of 5 average rating, 14 reviews

Condo on the Cove

Be our guest at our spacious multi-level Condo on the Cove. It's located across the water from the charming town of Carrabelle and just yards away from the Gulf! Pirates Landing Unit #280 has a guaranteed sea breeze year round. Enjoy the resort style pool, hot tub & gas grill just steps away from our unit! Boat launch, Marina & short term boat dock on the premises as well! It's perfect in every way!

Guest favorite
A sign for Pirates' Landing stands in the foreground, surrounded by lush greenery and palm trees. In the background, a multi-story building displays a series of balconies and windows. The clear blue sky enhances the coastal setting.
Townhouse in Carrabelle
4.93 out of 5 average rating, 169 reviews

Save a Ship ~ Ride a Pirate!

Hammock Time Too ~ a solid gold ❤️ Romantic Escape ❤️ for a Captain & First Mate. Remote & secluded, yore ‘get away’ is on the Gulf of America. Feel marooned yet close to charming Carrabelle Beach. Overlook a Key West style courtyard with sun warmed swimin hole & hot tub. Hammock Time Too offers 2 BICYCLES & a two~person KAYAK w/ gear. Courteous smoking allowed on screen porch.

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