Holiday rentals with a pool in Gulf County

Bay Breeze Cottage

Welcome to our charming coastal retreat in Barefoot Cottages. Close to Pool and Fitness Center, on-site grill and hot tub and equipped with private outdoor upstairs seating and fire pit perfect for enjoying your morning coffee or evening cocktails! Both bedrooms have queen beds and en-suite bathrooms. Beach chairs, towels, cooler, & bodyboard provided for your days at the beach. Located .5 mile from pristine beaches of Port St. Joe and convenient to local shops, restaurants and attractions.

Escape to St Joe Beach at Villa Blanca-Heated Pool

-Welcome to the Chic Beach Retreat, Villa Blanca, where you'll be greeted by ultra tall 26’ ceilings -Private Heated Pool - Gated Separately - Designed for Relaxation & Enjoyment -Nestled along the tranquil shores of St. Joe Beach, FL -Perfectly situated 1 block in from the gently lapping waves of the Emerald Coast -This charmer on 14' tall stilts, is a one-of-a-kind escape for those seeking serenity & style with tons of outdoor living space -Pet friendly-2 pup max < 30 lbs -Peekaboo Gulf View

Stunning Beach Front-Private Heated Pool & Beach

This 4000 sq-ft stunning, gulf front beach home is located in the quaint, coastal beach town of Port St Joe. Your own private beach, spectacular water views from all 3 floors and a private heated pool create the ultimate space for relaxation and enjoying family. This ultra spacious, stylish home sleeps 16. All bedrooms have king sized beds (2 have bunks for kiddos as well), en-suite bathrooms. It features a large open floor plan for kitchen/living/dining area. It is 1 mile to Mexico Beach

4bed/3bath l In-Law Ste l Golf Cart l Resort Pool

Welcome to Boardwalk Bungalow in Windmark! Everything you need for a fun, relaxing stay: a screened in back porch, an open main living/dining room, four luxurious bedrooms, three fully stocked bathrooms, a private in-law suite featuring a king size bedroom, bathroom, separate living room and full sized kitchen and 6 seater golf cart! Boardwalk Bungalow is a 5 minute golf cart ride to the resort-style pool or any of the 10 beach access boardwalks which feature convenient golf cart parking.

2 mins to beach, Poolside + Hot Tub, Fully Stocked

Best location in Port St. Joe! - Spikeball & cornhole - Yoga mat - Beach towels and chairs - Stocked kitchen w/ drip and k-cup machines - 2 Screened porches (200 sq ft) - Minutes to multiple beach access points - Central to cape san blas, mexico beach, and downtown PSJ - Upgraded kitchen - Smart TVs - Upstairs: 2 King Beds with en suite bathrooms - Downstairs: half bath, 1 sectional and 2 twin air mattresses for extra sleeping We prioritize your 5-star experience over anything else! :)

6 Min Walk to Beach–HeatedPool,GolfCart,bikes&BBQ

🏖 Welcome to Dream by the Sea, a luxury beach vacation home of "Tranquil Staycations. 🏝 If you're looking for a dream beach vacation that is private yet just a short distance from the beach and all the action, then look no further! Come experience Dream by the Sea, a new, clean luxurious well-designed beach house with modern coastal vibes in Windmark Beach community—BEST location in Port St Joe! luxury & amenities is great for family getaways! Community pool heated till March 2025.

Entire house with In-Law Suite and Golf Cart

This home is the perfect vacation rental for families looking to enjoy the beautiful beaches of Port St. Joe. With four bedrooms, two kitchens, and two living rooms, there is plenty of space for everyone to relax and unwind. Just a quick 2 minute golf cart ride from the beach, guests can spend their days soaking up the sun and enjoying the sand and surf. For those looking to cool off without the sand, the pool is just as close, offering a resort-style experience for all guests.

*Sunset Gulf View* | See & Hear the Waves! Pool •

**NEW: 10% off discount for 7 or more days** Tidelands at Mexico Beach by StayTheOne is a special find. And you found it! Just opposite the beachfront houses, it is almost beachfront. You will love the amazing Gulf-facing view, Pool & Hot Tub, gorgeous interior, and central walkable location in Mexico Beach. Well-appointed and comfortable, Tidelands is one of the top properties in town. It is on the 2nd floor of The Club at Mexico Beach and is accessible by elevator or stairs.

Shimmering Tides~Golf Cart~Secluded

Shimmering Tides is a perfect secluded home nestled at the end of a cul-de-sac in the charming community of Windmark Beach. Very private home perfect for making memories and relaxing! Screened porches allow gulf breezes to flow in while you unwind watching sunsets. Boardwalk is conveniently located within feet of the home taking you directly to the sugary sands & beach in less than 5 minutes. Spacious backyard, fire pit, all your beach amenities & GOLF CART included!

Heated Pool Southern Mermaid Cottage Pet Friendly

Welcome to Southern Mermaid Cottage! Located in the laid back town of Port St Joe just 800 ft from the beach, this is the perfect retreat from day to day life. Come stay with us and unplug without compromising modern amenities and comfort. Top of the line kitchenware, indoor and outdoor dining, fenced-in yard with large heated pool, grill and sitting area, beach gear, bikes, outdoor shower and more, this property will make your next vacation a memorable one.

GolfCart! E-bikes! Heated Pool! Arcade! Fire Pit!

Welcome to "Gone Coastal" Enjoy all that Windmark Beach has to offer with a relaxing stay in this newer home is a 4 bedroom, 2 bath home that is one of the closest homes to the town center and main pool. It is 2 blocks from the beach, a easy 5 min walk or short bike ride to the beautiful white sand of the Gulf coast. This home features all the amenities such as bikes (including two ELECTRIC bikes), 2 paddle boards, and a 6-seater golf cart all included!

4BR Beach Home w/ Fire Pit & Gulf Views

Welcome to your coastal escape in Port St. Joe - where ocean views, soft breezes & easy beach days await! Enjoy the perfect blend of comfort, relaxation & family-friendly fun: - Sleeps 8 | 4 bedrooms | 5 beds | 2.5 baths - Private outdoor pool (Heated w/fee) - Gulf-view decks w/ BBQ & outdoor seating - Fully fenced backyard w/ fire pit - Beach access just 300 steps away + beach essentials - Pet-friendly ($150 per pet, max 2)