
Holiday rentals with a pool in Wakulla County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Wakulla County
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Tiki Hut Sunsets • Fish, Relax & Explore FL Coast
Tucked away on Florida’s Forgotten Coast, this cozy RV escape offers peace, sunsets, and serious fishing. Your reset button awaits. 🌅 Private tiki hut w/ waterfront sunset views 🎣 Inshore & offshore fishing – grouper, trout & more 🚴♀️ 35-mile bike trail to Mashes Sands Beach 🍤 4 restaurants within 5 miles – incl. Angelo’s Seafood 🌊 45-min scenic drive to St. George Island 🔥 Laid-back, peaceful Old Florida vibes 🏈 45 minutes to Doak Campbell Stadium - home of the Florida State Seminoles

Coastal Cottage- on the Bay
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. A new home is being prepared for occupancy next door.

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!

Island Time Cottage.
Paradise awaits you in this rustic getaway. Island Time a located on Timber Island in a gated community on Carrabelle River. Mile to town & Carrabelle Beach. PCB 1.5 hour, St George Island, Apalachicola, Cape San Blas & Mexico Beach as you make your way. All you need on the Forgotten Coast. Carrabelle is known for the best fishing. The sunrises and sunsets are breathtaking from private boat dock or upper deck. Perfect for lil getaway for 2 or 4. Queen air mattress available upon request.

Waterfront Renovated condo with sparkling pool
We completely renovated this condo in July 2020. Ground floor condo located at George’s Lighthouse Point on Ochlockonee Bay. Large back porch has a beautiful view of the boat basin & side view of the bay. Walking distance is Angela’s restaurant, regularly voted as one of the top 100 restaurants in Florida. Beautifully decorated 2 BR with 920 ft.². King size BR & bunk room with full-size beds. Updated kitchen with every day amenities. All new bathroom including new tiled shower and vanity.

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.

Heavenly Hideaway: Waterfront, Pool, Fishing, Golf
The Heavenly Hideaway is a newly renovated beachfront home perfect for enjoying your own private retreat or to explore the Forgotten Coast. The area is known for spectacular fishing, scalloping, kayaking, & hiking w/ golf course 5 min away. Use the dock for fishing/docking your boat. Spend time sunbathing next to the pool or on the sandy beach. Plenty of parking for your boat/RV. Gorgeous ocean views directly from the open living/dining room, large deck or screened in porch. Visit today!

Starry Night: 3,800sqft sleeps 16! 1-min to 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.

Bayside Oasis: Pool, Tiki Hut, Pickleball & Slip
- Spacious 40 ft Glamper with king bed, recliners and 2 sleeper sofas - Dock - Resort Pool - pickle ball - keyless check in - on-site parking for up to 2 vehicles - picnic table with waterfront views - fully equipped kitchen - smart TV in living room - 10 min to bald point state park - 25 min to ochlockonee river state park -15 min to alligator point Beach - 6 min to Mashes sands Beach -5 min to Mashes sands boat ramp - convenient to multiple local restaurants

Charming Home in St. Teresa, FL
Welcome to Southern Pines Hideaway, our newly constructed vacation home in Summer Camp Beach West, a laidback, waterfront community located in St. Teresa, along Florida’s Forgotten Coast, on Coastal Highway 98 where the pine trees meet the beautiful Gulf of Mexico. The house has water access through a walking path approximately two hundred feet long from the yard directly to the beach. You can also relax at the community pool, a short five-minute walk from the house.

River Sanctuary Retreat
A newly renovated modern style spacious space for 2 people. It is close to Ochlockonee State Park, where time stands still on the banks of the river, allowing guests to experience the real Florida. The diverse wildlife inhabits the area, and there is a small shared pool onsite. Additionally, there is a river swimming area half a mile away and the ocean a few miles away. The space provides a peaceful retreat away from the hustle of life, surrounded by nature.

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.
Popular amenities for Wakulla County rentals with a pool
House rentals with a pool

Trifecta

Pure Bliss

Coastal Chic Bay Breeze

Blu Pearl

The Seabreeze Retreat with community pool

Family Tree - Monthly Rates Available

Relax at The Seagrass Cottage

Pines to Palms
Apartment rentals with a pool

Welcome to Fishes Fore Sail.

A Breezy River - River Front Condo with pool!

Captain Mac's Shack- Riverfront with Bay views

Fisherman's Rest Town House

Gotta Catch A Phish! 1BR/2BA Condo at Pirate's Lan

Lattitude Adjustment 1BR/2BA condo

Flip Flop- Flip to the pool or Flop to the beach!

Robin's Nest
Other holiday rentals with a pool

Paradise by the Sea

NEW Coastal Cottage with Private Pool and Dock

Hibiscus Cottage

Riverfront RV lot in Carrabelle, Florida

Charming Coastal Townhome Near Beaches

NEW Florida Resort Townhome Near Beach

Luxurious Country Guest Suite near Tallahassee

NEW Florida Coastal Cottage with Pool and Dock
Destinations to explore
- Rentals with lake access Wakulla County
- Flat rentals Wakulla County
- Pet-friendly rentals Wakulla County
- Beachfront rentals Wakulla County
- Hotel rooms Wakulla County
- Rentals with a hot tub Wakulla County
- Rentals with a firepit Wakulla County
- Rentals with a patio Wakulla County
- Rentals with outdoor seating Wakulla County
- Rentals with a washing machine and dryer Wakulla County
- House rentals Wakulla County
- Family-friendly rentals Wakulla County
- Rentals with a kayak Wakulla County
- Rentals with a fireplace Wakulla County
- Apartment rentals Wakulla County
- Rentals with pools Florida
- Rentals with pools United States




