Vacation rentals with a pool in Wakulla County

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!

Location · Family · Amenities

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.

Location · Value · Access

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!

Location · Family · River

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!

Value · Location · Comfort

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.

Check-in · Amenities · Hospitality

Shell Point bungalow with private pool and dock

Private Pool & Boat Dock • Walk to Shell Point Beach • Old Florida Charm Escape to our charming 1970s coastal bungalow, a 2-bed/2-bath retreat blending Old Florida character with modern style. Perfect for 2 couples or small families, this home features a private pool, a boat dock with Gulf access, and a fenced yard. Enjoy a peaceful getaway just a short walk from Shell Point Beach. Comfortably sleeps your group in a serene, stylish setting.

Location · Family · Parking

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.

Value · Family · Bathroom

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.

Location · Family · Bathroom

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.

Family · Location · Kitchen

NEW Coastal Cottage with Private 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.

Family · Location · View

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!

Family · Location · Cleanliness

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.

Family · Value · Long stay