Holiday rentals with a pool in Port St. Joe

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.

4.98 out of 5 average rating, 42 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.

A collage of the Sunset Shores Beach House highlights features of the property, including the sparkling community pool, a six-seat golf cart for convenient access, and stunning Gulf of Mexico views. The layout showcases the welcoming home environment and the nearby beach access.

5.0 out of 5 average rating, 102 reviews

Steps2Pool/Mins2Beach/GolfCart/FirePit/Beach Equip

⭐️Luxury 4-bedroom Beach Home ⭐️ Sleeps 12 in Windmark Beach ⭐️ Heated Pool Oct 1-Apr 30 ⭐️ 6 Seat Golf Cart ⭐️ Steps to Beach Access ⭐️Pet Friendly You’ll be steps to the luxurious community pool where you can relax overlooking the Gulf. You can walk to the beach in mins from the home to swim in the warm waters of the gulf or relax in the sun.Take a golf cart cruise to the nearby Village Center to grab a bite to eat.End your day relaxing in the screened-in porches or fire pit outdoor space.

An aerial view of the gulf front beach home reveals three neighboring structures amidst lush palm trees. The private beach extends along the shoreline, showcasing calm turquoise waters. The inviting exterior features a light-colored façade and expansive decks, emphasizing the home's proximity to the water.

4.88 out of 5 average rating, 95 reviews

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

5.0 out of 5 average rating, 22 reviews

The Bay Shack 4BR + MIL Suite, Port St. Joe

Welcome to The Bay Shack in Windmark Beach— your coastal retreat in Port St. Joe, Florida, situated on the St. Joseph Bay and minutes to Mexico Beach and Cape San Blas. This spacious 4-bed, 3-bath home includes a 3BR/2BA main house plus a private 1BR/1BA mother-in-law suite with its own entrance, ideal for multi-generation families or couples traveling together. Unwind after a beach day on the covered porch, cook fresh local seafood in the fully equipped kitchen, and catch stunning sunsets.

The living area is adorned with a vibrant orange armchair, complemented by a cozy grey sofa. A large flat-screen TV displays a scenic ocean view. Decorative elements include a potted plant, a modern clock, and a coffee table centerpiece, contributing to a relaxed atmosphere.

4.94 out of 5 average rating, 90 reviews

5-min Walk to Beach*Steps to Pool & Fun Amenities*

Coastal Gem is a brand new constructed beach home located at Windmark Beach North Community. This home is decorated with coastal décors and provides comfortable cozy beach vibe for your family vacation. Our home has 4 bedrooms and 3 bathrooms including the IN-LAW SUITE. It's attached to the main house with a separate unit offering more privacy included: Master bedroom, full bathroom, living room space, full stocked kitchen, laundry room and private access to Florida Scallop, Music & Arts

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.

5.0 out of 5 average rating, 31 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.

4.87 out of 5 average rating, 15 reviews

Arcade, Golf Cart, Bikes, 2 Kitchens plus more

Experience laid-back coastal living in this bright and spacious 4-BR, 3-BA home in WindMark Beach. Enjoy free parking, beach gear, and a 6-seater golf cart for easy getting around. The home comfortably sleeps up to 10 guests and features a private in-law suite with its own kitchen, two separate living areas, and a fun arcade space. Located minutes from the beach and WindMark Town Center’s dining, pool, and entertainment, with quick access to Port St. Joe and Cape San Blas.

4.97 out of 5 average rating, 257 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! :)

4.96 out of 5 average rating, 142 reviews

A Shore Delight-Beach Retreat•Pool and Gulf Views

Your Gulf-view retreat in Port St. Joe! - Sleeps 8 | 4 bedrooms | 5 beds | 2.5 baths - Private outdoor pool (open 24hrs year-round; heating Oct-Mar, fee applies) & outdoor shower - Gulf-view decks w/ gas BBQ grill & fire pit in fully fenced backyard - Beach access 300 steps away w/ beach essentials (chairs, towels & umbrella) provided - In-unit W/D, smart TVs, high-speed Wi-Fi & dedicated workspace - Pet-friendly (up to 2 pets, $150/pet non-refundable fee)

4.9 out of 5 average rating, 135 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!

5.0 out of 5 average rating, 6 reviews

WindMark Retreat | Golf Cart + 2 Pools

Welcome to Making Mo Memories, a family-friendly coastal retreat in the beautiful WindMark Beach community. Sleeping up to 10 guests, this thoughtfully designed home features a 6-passenger golf cart, beach gear, screened porch with bay views, and access to 2 resort-style pools. Just minutes from the beach, playgrounds, walking trails, dining, and shopping, it's the perfect place to relax, reconnect, and make lasting memories on Florida's Forgotten Coast.

An aerial view captures a cluster of beachside homes, with a clear view of the ocean and coastline in the backdrop. Lush greenery is visible in the foreground, complementing the sandy shores. The horizon features soft clouds against a bright blue sky, enhancing the coastal atmosphere.

4.98 out of 5 average rating, 52 reviews

Golf Cart EVCharger POOL Walk to Beach 2 Kitchens

New 2023 luxury beach retreat in Windmark—boardwalk 2 houses away + resort pool walkable. Includes a 2025 6-seater golf cart + Tesla Level 2 EV charger + bikes/beach gear. Perfect for a large family: 4BR/3BA with a private in-law/teen suite + TWO full kitchens. Walk or ride our bikes 700 feet to the beach. Located in North Windmark closest to Mexico beach. Beautiful peek a boo views of the ocean from your back porch. Walk to the boardwalk.

Popular amenities for Port St. Joe rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

5.0 out of 5 average rating, 118 reviews

Shimmering Tides~Golf Cart~Secluded

The exterior features a light-colored cottage with palm trees and vibrant landscaping. A golf cart is parked in the driveway, providing easy access to nearby amenities. The house is set against a clear blue sky, emphasizing the inviting atmosphere of the coastal retreat.

5.0 out of 5 average rating, 30 reviews

New 4BR|2 Two Kitchens|Golf Cart|Walk to Bay/Pools

A modern living area features a comfortable blue sofa alongside two round chairs, set upon a textured area rug. Wall art is displayed above a round coffee table, and a dining area is visible in the background, with natural light filtering through large windows.

4.95 out of 5 average rating, 22 reviews

Coastal Retreat+Walk to Beach+Pool+GolfCart+Arcade

5.0 out of 5 average rating, 23 reviews

Hot Tub, Fenced Yard, Close to Beach Dining Pool

4.88 out of 5 average rating, 16 reviews

K&K’s Coastal Getaway/Beach Access/Pools

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.

5.0 out of 5 average rating, 37 reviews

Windmark beach house with MIL suite/ Golf cart

The beach home is a two-story structure painted in light turquoise with white trim. A welcoming front porch features multiple rocking chairs and is framed by palm trees. A sandy driveway leads to the entrance, while the surroundings showcase well-maintained landscaping and open spaces.

5.0 out of 5 average rating, 78 reviews

Cape San Blas private beach house Port St Joe

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.

4.93 out of 5 average rating, 29 reviews

Home w/ 2 Master Suites (golf cart included)

Condo rentals with a pool

The pool area is highlighted by a heated pool and a hot tub surrounded by brick paving. Lounge chairs and a table with chairs provide seating options. Palm trees and a view of the ocean can be seen in the background, under a partly cloudy sky.

4.9 out of 5 average rating, 114 reviews

Sept/Oct Reduced! Oceanview, Pool, Sauna & Jacuzzi

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, 125 reviews

Grand Balcony Views, Pool, Hot Tub

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.

4.94 out of 5 average rating, 32 reviews

Beach, Breeze, Balcony Dreams

Superhost

An expansive deck features two blue adirondack chairs, overlooking the serene beach and Gulf waters. The sunset casts warm hues across the sky, creating a peaceful backdrop against the sandy shore and distant waves.

Condo in Port St. Joe

4.71 out of 5 average rating, 14 reviews

SeaScape: 4BR 1st-Floor Condo, Beachfront,Pool/Spa

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.

5.0 out of 5 average rating, 50 reviews

Wonderful 3/3 condo with 2 covered balconies

5.0 out of 5 average rating, 22 reviews

Smokey's Sunset at Mexico Beach

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.

4.97 out of 5 average rating, 29 reviews

2/2 Waterfront Condo with pool and hot tub

Superhost

5.0 out of 5 average rating, 3 reviews

180 Gulf Views 3/2 in Summerhouse

Other holiday rentals with a pool

4.96 out of 5 average rating, 25 reviews

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

4.98 out of 5 average rating, 41 reviews

Family Beach Retreat with Golf Cart and Beach Gear

5.0 out of 5 average rating, 33 reviews

Fall Special! Golf Cart•Pools•Beach•Game Room

Superhost

5.0 out of 5 average rating, 3 reviews

NEW! Views | Steps to Beach | Pool | Elevator |

4.95 out of 5 average rating, 19 reviews

A Twist of Lime

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.

4.91 out of 5 average rating, 68 reviews

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

The exterior of a two-story blue beach cottage is surrounded by palm trees and lush greenery. A screened porch is visible on the upper level, providing an inviting outdoor space. A paved pathway leads to the entrance, enhancing accessibility to the home.

4.98 out of 5 average rating, 90 reviews

Bebe’s Beach Cottage

A serene outdoor view features a porch with an American flag gently waving. The horizon displays a gradient of soft colors as the sun sets over the calm ocean, with a beach area visible in the foreground.