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.

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

4 BR Beach House | Golf Cart + Hot Tub + Fire Pit

Sandy Bottom at WindMark Beach offers easy, elevated beach living with a private hot tub, fire pit , and outdoor dining + grill. Just a quick golf cart ride to the beach and village. Golf cart with cooler + cargo attachment, beach gear & bikes included. Relax on the front porch daybed lounger or enjoy climate-controlled garage hangout. Fully stocked kitchen, on-site EV charger, & all the essentials thoughtfully provided. Because the best days end with sandy bottoms and time well spent together.

Book your summer getaway now/ golfcart to beach!

Come indulge in the peaceful hidden treasure of Port Saint Joe! Enjoy our community pool 2 min. from the home. Shops and restaurants are within a two minute private golf cart ride. Two blocks from the beach with upfront golf cart parking! This spacious four bedroom home is perfect for multiple families to gather and make memories together! Our home is kid friendly with a sea turtle theme room and toys awaiting them! This spacious home has two queen bedrooms/kids bunk room/king master suite.

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.

Gulf-view retreat w/ pool, decks & fire pit

Welcome to your St. Joe Beach Gulf Coast retreat - a four-bedroom home steps from the water. - Sleeps 8 | 4 bedrooms | 5 beds | 2.5 baths - Private pool (open 24/7, year-round; heated Oct-Mar - fee applies) w/ fire pit, gas BBQ & sun loungers ~300 steps to the beach w/ beach essentials - Gulf-view decks, Wifi & dedicated workspace - Family extras: crib, Pack 'n play, baby gates, kids' books - Pet-friendly ($150/pet) | Free carport parking (3 spaces) | Self check-in via keypad

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! :)

Your Independence Day Beach Weekend Starts Here

Welcome to your Independence Day 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.

Private LUX Oasis | 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

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

✨ A Pink Door Vacay Signature Stay ✨ -Welcome to Villa Blanca, a chic beach retreat with soaring 26’ ceilings and breezy coastal design. -Enjoy a private, separately gated pool made for relaxation and fun. -Nestled along the tranquil shores of St. Joe Beach, just 1 block from the Emerald Coast. -This one-of-a-kind home sits on 14’ stilts with expansive outdoor living. -Pup friendly - 2 pups <30 lbs

Tipsy Turtle Oceanfront Beach House!

Escape with the family to Tipsy Turtle - a 3500 sq ft haven for casual living and entertaining. Revel in a well-equipped home, stunning sunsets, dolphin and seasonal turtle sightings, and a tranquil beach. Explore nearby Cape San Blas, Port St. Joe, Indian Pass, and Apalachicola for fantastic dining and shopping. Make Tipsy Turtle your retreat for unforgettable getaways!

The Chartroom

Luxury 4BR/3BA bayfront home beside the St. Joe Marina. Sleeps 10 with a king suite, two queen rooms, and a twin room. Enjoy the community pool, small sandy beach, and stunning bay sunsets. Walk to downtown Port St. Joe, shops, restaurants, and the lighthouse. Short drive to St. Joe Beach, Cape San Blas, and Indian Pass.