Holiday rentals with a pool in Gulf County

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.

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

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.

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!

4.97 out of 5 average rating, 239 reviews

A screened porch entrance opens to a clear pathway leading to the pool area. Lush palm trees and well-maintained shrubs are visible, creating a welcoming view of the community's outdoor space.

Cottage in Port St. Joe

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

Best location in Port St. Joe! - Spikeball & cornhole - Yoga mat - 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! :)

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.

4.99 out of 5 average rating, 68 reviews

Walk to beach, pool, golf cart & bikes

⭐️ Community HEATED pool ⭐️ Heated October thru April ⭐️ Sleeps 10 ⭐️ Bunk Room with 4 twin beds ⭐️ Screened In patio w/ seating ⭐️ Camp Chef Flat Top Grill ⭐️ Garage / Game Room ⭐️ Air Hockey Table ⭐️ Golf Cart ⭐️ 4 adult bikes ⭐️ 2 Paddleboards ⭐️ Beach Wagon ⭐️ Beach Chairs ⭐️ Beach Towels ⭐️ Sand Toys ⭐️ 5 Smart TV's ⭐️ Washer and dryer ⭐️ Keyless entry ⭐️ Wifi ⭐️ 2 parking spaces ⭐️ Community fitness center - day pass available for purchase

5 out of 5 average rating, 44 reviews

Cottage in Port St. Joe

Family Beach Retreat | 3 Pools & White Sands

Welcome to your Spring Break family getaway in Port St. Joe! This 2BR/2.5BA coastal cottage is near the calm waters of St Joseph Bay, Windmark, St Joe, and Mexico Beaches. The beautiful beaches of Cape San Blas are just minutes away. Enjoy a bright open layout, full kitchen, two porches, plus access to 3 community pools and a hot tub—perfect for relaxing after beach days, kayaking, and family adventures on Florida’s Forgotten Coast.

5 out of 5 average rating, 28 reviews

LUX Beach Retreat | Pool, Game Room, Dog Friendly

★ HUGE {heated w/fee} Private Pool ★ 1 (easy) block to the beach ★ Loaded Game Room (Pac-Man, X-Men, NBA Jam) + Shuffleboard + 65in TV ★ Dog Friendly (up to 2 w/pet fee) ★ Screened Lanai overlooking pool w/NEW 65in TV ★ Private fenced backyard ★ Fully Stocked Coffee Bar ★ Tons of beach essentials included! (chairs, umbrella, beach cart, beach towels) ★ Boat + RV Parking onsite

Superhost

The exterior of a newly built cottage is shown, featuring a welcoming front porch with two chairs. The entrance is framed by large windows, and neat landscaping includes palm trees, offering a spacious concrete driveway and a sense of openness.

4.84 out of 5 average rating, 44 reviews

The Oyster House

Stylish 3BR/2BA coastal retreat sleeping 8. Enjoy a private pool with full privacy fence, set in a golf cart–friendly neighborhood near downtown Reid Ave. Walk or ride to restaurants, shops, St. Joseph Bay, and Lighthouse Park. A paved trail, park, and playground sit just behind the home — perfect for families and outdoor lovers. Relax, unwind, and live the easy-going Port St. Joe lifestyle.

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, 50 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.