Holiday rentals with a pool in Carrabelle

Riverfront Condo on Beautiful Apalachicola River!

Wonderful Riverfront condo located on the serene Apalachicola River. Expansive screened in patio offers breath taking water views. Perfect for watching boats & Florida wildlife. Convenient walk to the shops & restaurants of charming downtown Apalachicola. Master bedroom has a king bed with water views and balcony access. The second bedroom has a full size bed and private bath. Only steps to boat slips that can be reserved through Water Street Hotel & Marina. Swimming pool & gym access included!

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.

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.

Redfish: view, pool, steps2beach

Just over the dune line road from quiet east end beaches. Great fishing and uncrowded relaxing. Excellent for families or couples (4 person maximum) with private spaces indoor and out. Two master bedrooms with kings and pillow tops. Second floor remodeled and decorated (photos Feb 2026). Shared pool and gulf views from front room and master. Front Deck. Large furnished screened porch. You will be hard pressed to find a better spot for your vacation dollars. Beach wagon, canopy and chairs.

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!

Pines to Palms

Pines to Palms is a great place to stay in Carrabelle. Plenty of room for family, friends, and your boat. Two minutes to the boat ramp, two minutes to the river walk and downtown, less than five minutes to Carrabelle Beach, and less than 30 minutes to St George Island. Experience this amazing gem of a town of Florida's forgotten coast. Don't cram in a small space. Enjoy 1,500 square feet and a friendly townhouse community with a pool. This is a non-smoking property inside and out.

Solaria: Waterfront, Pool, Fishing, Kayak, Golf

Solaria is a quaint, gorgeously-updated waterfront retreat with sunset views, offering convenient access to St George Island, Historic Apalachicola and more! There are 4BR/3BA with an open living room/kitchen attached to screened porch, outdoor fire pit and heatable pool, and plenty of space for entertaining/dining. Fish/kayak on the bay at home, or enjoy great restaurants/boutiques and the beach within minutes. Or just escape for some peace and quiet. Come and Explore today!

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

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! Waterfront Restaurant coming soon! It's perfect in every way!

Reelin' in! Community Pool! 2 BR/ 2 BA

Your family will be close to everything! 2 mins to public beach! 2 mins to riverfront with shops and restaurants! Reelin em in is for bargain friendly families! 2 bedrooms and 2 bathrooms plus a sleeper sofa and a community pool! Perfect! Well equipped kitchen with all the gadgets. Covered porches and charcoal grill for preparing your fresh catch. This home has all you need and is perfectly located for all Carrabelle has to offer!

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.

lily’s Escaped, Waterfront, pool,fishing, golf

The lily’s Escape is a newly renovated oceanfront property perfect for a family getaway, the area is just few minutes from the st James bay golf course, few minutes from down town carrabelle there have shops and restaurants,carrabelle beach (6 miles), ochlockonee river state park (13 miles), crooked river light house (10 miles), orman house historic state park (30 miles)