Holiday rentals with a pool in Gulf County

4.86 out of 5 average rating, 29 reviews

Bayfront | Heated Pool | 100% Private Beach | Dog

NEW! Just added HEATED POOL to the property! Enjoy a refreshing dip just steps from your door - perfect for relaxing after a day at the beach or soaking up the sun right at home. Welcome to Happy Ours Beachfront Getaway from FunGetawayRentals! 🌞 All guests staying at the property will receive a $250/day BONUS, with free rentals of 3 single kayaks (including vests & paddles), 3 paddleboards and 3 coastal bikes - a $250 value, on us! Perfect for your beach adventures! Note: Liability waivers mus

A two-story coastal cottage is presented with a covered porch featuring outdoor seating. Lush greenery surrounds the exterior, enhancing the relaxing ambiance. The pale blue façade and white railings contribute to the inviting atmosphere of this retreat.

5 out of 5 average rating, 20 reviews

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.

Townhouse in Port St. Joe

A panoramic view captures a vibrant sunset over the serene Gulf waters, with hues of orange, pink, and purple blending into the sky. Soft waves lap against the sandy beach, where silhouettes of people can be seen enjoying the evening. A wooden fence borders the foreground, adding a rustic touch.

4.96 out of 5 average rating, 53 reviews

2 Bedroom, 2.5 Bath in Beach Community - Sleeps 6

Experience Cape San Blas charm at our 2 bedroom, 2.5 bath townhome. You're just a short walk to the stunning emerald Gulf waters-perfect for lazy beach days or adventures. Take a dip in the gulf-front pool or the 2nd seasonally heated pool. Whether you're into beachcombing, bonfires, fishing, or catching those epic Cape sunsets, you'll create memories here. Indulge in the comfort of our home, boasting hard surface flooring, a well-appointed kitchen, and inviting spaces to unwind and relax.

5 out of 5 average rating, 10 reviews

Sunset | Golf Cart | Walk to Beach | Pool | Bikes

Indulge in the ultimate coastal getaway near the sandy beaches and clear waters. This peaceful retreat has the modern amenities of a resort with the privacy of a luxury home. Enjoy stylish living areas, a modern kitchen, and a patio overlooking tranquil water. Drive the golf cart to the Village Center to swim in the heated pool or grab a bite. Windmark Beach – 4 min drive Lighthouse – 10 min drive Convention Museum – 12 min drive Book For Lasting Memories In St. Joe—See Details Below!

The exterior of a single-family coastal home is illustrated, featuring a light-colored façade and a driveway with a blue golf cart parked nearby. Two white chairs are positioned on the front porch, flanked by palm trees and landscaped greenery, creating an inviting entryway.

5 out of 5 average rating, 21 reviews

Nash In The Sand

Welcome to Nash in the Sand. Your Luxury Beach Home Rental in Windmark Beach. This new construction luxury designed home has everything you need for an Amazing beach vacation. Located within walking distance or short golf cart ride to the BEACH. This single family home offers coastal luxury with 4 spacious bedrooms. 2 bathrooms, fully stocked kitchen, laundry room, front and back porches, Flooring consists of LVP, quartz countertops, stainless appliances, luxury linens and pillows.

A spacious living area features a comfortable sectional sofa with decorative pillows. A large area rug adds color to the warm-toned wood flooring. A console table holds a lamp, while a kitchen area is visible in the background, highlighting the open-floor plan.

5 out of 5 average rating, 17 reviews

Slack Tide

Don’t miss the most spectacular sunsets on the Forgotten Coast. Our charming 4 BR, 2 Bath house is beautifully decorated and sleeps up to 11 people just a golf cart ride away from downtown Windmark and the beach. This house comes with bedrooms that have plenty of space for your personal items, a fully equipped kitchen, WiFi, access to Windmark’s pool and it’s downtown features. We hope it doesn’t happen, but in case there’s rain, we got the games! Golf cart included!

An aerial view reveals a spacious home flanked by lush greenery and sandy paths, leading towards the beach. Nearby structures and coastal vegetation create a serene environment. The calm blue of the ocean is visible in the distance, highlighting the home's proximity to the shoreline.

5 out of 5 average rating, 113 reviews

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!

A fenced-in backyard features a large, heated swimming pool adorned with colorful flotation devices. Several lounge chairs are positioned around the pool, and shaded seating is provided under a blue umbrella. Lush greenery complements the serene outdoor space.

4.98 out of 5 average rating, 45 reviews

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.

4.9 out of 5 average rating, 121 reviews

Golf Cart! E-bikes! Heated Pool! Arcade! FirePit!

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!

A private pool is framed by a stone patio, featuring lounge chairs and umbrellas for shade. The pool area is bordered by palm trees, and a sliding door provides access to the indoor living space. The sky above displays a mix of blue and fluffy clouds.

4.9 out of 5 average rating, 49 reviews

3BR/2BA Cottage w/PRV POOL Marina District

Enjoy luxury lodging at The Captain’s Quarters cottage located in the epicenter of the Marina District w/pool. Conveniently located next to Port St Joe’s Haughty Heron and adjacent to Point South Marina and only a 2 block walk to the shops and local eateries on Reid Avenue in Downtown Port St Joe’s Historic District. Whether traveling by land or sea, this cottage is the place to be!

A spacious living area features large windows that provide abundant natural light and stunning bay views. The room is furnished with comfortable seating, a decorative fireplace, and coastal-themed décor, inviting relaxation and connection with the outdoor surroundings.

4.94 out of 5 average rating, 52 reviews

Twin Gables, Private Pool & Pet Friendly

Escape to Twin Gables, a luxurious bayfront retreat on 2.5 private acres in Cape San Blas. This single-level home offers panoramic bay views, a private pool with swim jets, and sleeps up to 4 adults and 2 children. Enjoy stunning sunrises from the screened porch, and relax in 'Old Florida' tranquility. Perfect for a serene family getaway, with charming towns just a short drive away.

A three-story beach home is surrounded by palm trees and tropical landscaping. The exterior features horizontal slats and a covered balcony above the ground level. The ground level includes a paved area with garage doors, offering parking and access beneath the house.