Holiday rentals with a pool in Port St. Joe

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, 22 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.

New place to stay

A Twist of Lime

Clean & colorfully styled coastal retreat features 3 bedrooms & 2.5 baths, with bedrooms located upstairs for privacy & quiet separation from the main living space. The home sleeps up to 9 guests, making it a perfect getaway for anyone looking to enjoy Florida’s Forgotten Coast. Outside, enjoy the desirable WindMark Community & access to 2 separate pools, bike trail & private golf cart path. The home is located less than 2 mins from the beach & includes use of a 4-seater golf cart if desired.

5 out of 5 average rating, 5 reviews

Golf Cart | Heated Pool | Arcade Games

Enjoy our family-friendly beach retreat just steps from WindMark Beach’s boardwalk. This 4-bedroom, 2-bath home sleeps up to 10 and features a serene king suite, 2 inviting queen bedrooms, and a fun kids’ bunk room. Enjoy an open-concept living space, gourmet kitchen, and private patio with Weber grill overlooking peaceful lake views. With bikes, beach gear, games, heated community pool, and a walkable location near dining and beach access, this home offers the perfect Port St. Joe escape.

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.

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 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.

4.97 out of 5 average rating, 240 reviews

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! :)

4.99 out of 5 average rating, 69 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, 45 reviews

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.

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, 52 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!

Popular amenities for Port St. Joe rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The exterior of the home is displayed, featuring a light-colored facade under a bright sky. A yellow four-seat golf cart is parked on the concrete driveway, providing convenient transportation for guests. Green landscaping adds a touch of nature to the entrance.

5 out of 5 average rating, 16 reviews

Entire house with In-Law Suite and Golf Cart

The exterior of a spacious beach house features a wide driveway leading to a covered entrance. Palm trees surround the front yard, and a golf cart alongside several bicycles are parked in front, emphasizing outdoor leisure and accessibility.

4.98 out of 5 average rating, 54 reviews

A Thoughtfully Designed Family Retreat in PSJ

A modern beach home exterior features a vibrant yellow facade and a two-car garage. Palm trees and low landscaping enhance the entrance, while the driveway provides ample space for parking. A clear sky hints at an inviting atmosphere for vacationers.

4.92 out of 5 average rating, 24 reviews

Home w/ 2 Master Suites (golf cart included)

5 out of 5 average rating, 4 reviews

Ocean & Pine | Golf Cart + Pools + Low April Rates

5 out of 5 average rating, 21 reviews

A spacious front porch features two white rocking chairs positioned on either side of a small table, while an inviting concrete driveway leads up to the house. The exterior walls display light blue and white colors, framed by lush green grass and slight landscaping.

Home in Mexico Beach

Salty Beach Bungalow

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

A modern beach house is illuminated at dusk, featuring a spacious deck with multiple levels. A luxurious pool reflects vibrant blue lights, while lounge chairs are placed nearby. An umbrella offers shade, and palm trees are visible in the background, enhancing the coastal setting.

4.94 out of 5 average rating, 18 reviews

North End Beauty-Gulf Side | Private Pool+Hot Tub

A spacious garage area is shown with two paddle boards mounted on the wall. Three beach bicycles are parked on the driveway alongside a six-seater golf cart. Lush palms add a touch of greenery to the exterior setting.

4.91 out of 5 average rating, 45 reviews

4bed/3bath l Golf Cart l MIL Suite l Bikes l 3 min

Apartment rentals with a pool

A view from the living room showcases the ocean, framed by large glass doors. Comfortable seating is positioned on the covered balcony, with cushions adding a touch of comfort. Lush greenery is visible outside, complementing the serene beach scene.

5 out of 5 average rating, 44 reviews

Wonderful 3/3 condo with 2 covered balconies

A spacious balcony offers a direct view of the Gulf, featuring a round dining table surrounded by chairs. Comfortable seating is positioned nearby. Bright artwork adorns the wall, complementing the coastal ambiance. The soothing sounds of the waves can be experienced from this inviting space.

4.98 out of 5 average rating, 116 reviews

Grand Balcony Views, Pool, Hot Tub

A corner seating area is presented with a natural wood bench adorned with three yellow-patterned pillows. A painted pelican artwork hangs on the wall above. A yellow woven basket is positioned nearby, complementing the neutral tones of the space.

5 out of 5 average rating, 30 reviews

Luxury Mexico Beach Condo Gulf views (First Catch)

An open entrance area is visible, featuring a wooden table and a chair on the left. Light blue walls create a calming backdrop, while a spacious kitchen is seen in the distance, with modern appliances and a ceiling fan. Natural light filters in through large windows.

4.94 out of 5 average rating, 17 reviews

2/2 Waterfront Condo with pool and hot tub

A dining table is set for two on the spacious balcony, featuring blue plates and glasses alongside a sparkling wine bottle. The ocean stretches in the background under a partly cloudy sky, offering a serene view of the beach.

4.95 out of 5 average rating, 22 reviews

Unbeatable ocean view from enormous balcony!HUGE 2

5 out of 5 average rating, 16 reviews

Smokey's Sunset at Mexico Beach

A spacious living area features a comfortable sectional sofa, accent chairs, and a decorative coffee table. Large glass doors provide views of the ocean and access to the balcony. Soft lighting illuminates the room, which includes a dining table and coastal-themed artwork.

5 out of 5 average rating, 17 reviews

Beach, Breeze, Balcony Dreams

Apartment in Port St. Joe

4.71 out of 5 average rating, 7 reviews

Too Easy - Gulf-Front with Community Beach & Pool

Other holiday rentals with a pool

A charming exterior view of the house is highlighted by the lush green lawn and palm trees, set against a vibrant sunset sky. The driveway leads to a garage, with a window suggesting warm light inside, indicating a welcoming atmosphere.

5 out of 5 average rating, 20 reviews

Sunset Beach House perfect for family vacation.

An aerial view showcases a triangular swimming pool surrounded by a stone deck, with several lounge chairs positioned around it. A smaller hot tub is located nearby. Lush palm trees and landscaped paths define the community area, enhancing the tranquil setting.

4.93 out of 5 average rating, 92 reviews

Gated w/pool & hot tub near beaches!

5 out of 5 average rating, 3 reviews

No Need to Rush

The exterior of Villa Blanca is showcased against a vibrant sunset, highlighting the two-story structure elevated on stilts. Outdoor seating and a private pool are visible in the backyard, with palm trees adding a tropical touch to the overall inviting atmosphere.

5 out of 5 average rating, 67 reviews

Villa Blanca-Private Pool - Walk to St. Joe Beach

5 out of 5 average rating, 12 reviews

A charming cottage with a vibrant green exterior is elevated on stilts, surrounded by a spacious lawn. A private cowboy pool is visible alongside a seating area. Large windows reflect sunset hues, enhancing the inviting ambiance of this outdoor space.

Home in Mexico Beach

Stay Salty, Sleep Luxe | Pool | 3 Kings

The exterior of a modern bay-front home is visible, featuring a white facade with multiple balconies. Large windows allow natural light to fill the space. The surrounding landscape includes sandy paths and native vegetation, creating a tranquil environment in the gated community.

5 out of 5 average rating, 11 reviews

The Salty Scallop

A vibrant collage highlights key attractions near the property. The image includes a community pool surrounded by palm trees, an orange golf cart designed for six passengers, bicycles parked for exploration, and a foosball table for entertainment. A sunset casts warm tones over the beach in the background.

5 out of 5 average rating, 28 reviews

Windmark beach house with MIL suite/ Golf cart

A screened porch offers a round glass table surrounded by four wicker chairs. Lush greenery and palm trees are visible in the background, creating a serene outdoor setting. Light filters in through the screens, enhancing the inviting atmosphere of the space.