Holiday rentals with a pool in Saint Joseph Bay

5 out of 5 average rating, 58 reviews

HeatedPool/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 ⭐️ Grocery Service ⭐️Pet Friendly You’ll be steps to the luxurious community pool where you can relax overlooking the Gulf of Mexico.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 yourday relaxing in the screened-in porches or fire pit outdoor living space.

5 out of 5 average rating, 31 reviews

5 Min To Beach, Golf Crt, In-Law Suite, Pool

5 min from beach! Everything needed for fun & relaxation: Open floorplan, 4 bedroom (2 King) 3 bath, private in-law suite w/ it's own living area, bathroom, kitchenette & bedroom. Game room and GOLF CART! Pickleball equipment provided for the courts just 10 min drive away! Windmark Beach- cart to the Village & enjoy shops and restaurants or resort style community pool. Neighborhood pool at the end of our street. Take your pick between 2 gorgeous beaches both accessible by walking or golf cart

Superhost

4.8 out of 5 average rating, 5 reviews

Barefoot Bungalow

Barefoot Bungalow at Barefoot Cottages is ideally located near great restaurants, charming shops, and pristine Gulf beaches—perfect for your next coastal escape. This inviting, well-stocked home ensures a relaxing stay, while cozy beds promise restful nights. The open layout comfortably suits couples or families, with delightful beach-inspired decor adding warmth and charm. Thoughtful amenities and a laid-back atmosphere ensure guests love their visit and eagerly look forward to returning.

4.98 out of 5 average rating, 210 reviews

Cottage in Port St. Joe

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

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

5 out of 5 average rating, 103 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!

4.96 out of 5 average rating, 122 reviews

Charming 4BD Beach House-Private Pool-Great Views

Scallop Season Dates Available ★ Private Pool ★ 300 steps to the beach ★ Ocean views from both decks ★ Sleeps 8 ★ Pet Friendly ★ Beach essentials included! (chairs, umbrella, beach cart, beach towels) ★ Large, private fenced backyard with lounge chairs and firepit Enjoy peaceful beach walks, the year-round luxury of a private pool (Heating option available Oct-Mar), morning coffee on the deck, and unforgettable family moments set against breathtaking sunsets.

4.89 out of 5 average rating, 103 reviews

Golf Cart! E-bikes! Heated Pool! Arcade! Fire Pit!

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!

4.98 out of 5 average rating, 49 reviews

Walk to Beach, Golf Cart, Pool, Bikes, Air Hockey

⭐️ 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 for purchase

4.8 out of 5 average rating, 15 reviews

Vet Owned | Private Pool | Pets OK | Walk to Beach

Escape to Casa Cancun, a spacious 4BR/3BA beach retreat just a 3-5min walk to the sugar-white sands of Cape San Blas! Sleeps 15 guests, featuring a private pool, Gulf views, pet-friendly space, and an entertainment room—perfect for families & groups. Relax on the screened-in deck, play ping-pong, or walk to local eats for fresh donuts & ice cream. Unwind in paradise with sun, sand, and serenity. Book your dream beach getaway today!

4.9 out of 5 average rating, 42 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!

Superhost

Apartment in Cape San Blas

4.64 out of 5 average rating, 36 reviews

Peaceful oceanfront condo with pool and kayaks

Come stay on the beach and wake up to the sound of the ocean. This oceanfront condo is the place to relax with your family and find some peace and quiet away from everything. This spacious condo has 25 windows looking right out at the beach. Your home sits right on the dunes! Walk out from the living room or two of the bedrooms and feel like you are sitting on the beach!!