Holiday rentals with a pool in Highlands County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Highlands County

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Superhost
The exterior of the duplex displays a single-story structure with a brown roof and light-colored walls. Lush greenery, including palm and ornamental plants, surrounds the entrance, while a driveway leads to a garage on the right side. Windows are accented by dark shutters.
Home in Sebring
4.77 out of 5 average rating, 111 reviews

Pet Friendly, Pool, Raceway Townhome.

Our AirBNB property duplex is located 3 minutes driving distance from Sebring International Speedway. 3 major lakes for fishing and boating enthusiats, and surrounded by fine restaurants and sunset grills.Sebring is a bikers delight as well, with light traffic and nice roads to tour. Our property is roughly 1 hour and a half by car from Tampa, Orlando &,Palm Beach. We welcome you to our page and are here for your travel needs. We offer beautiful gardens, beautiful pool, kitchen,bedrooms,& bath

Superhost
An open layout is displayed, showcasing a spacious living area with comfortable seating arrangements. A dining table is positioned near the kitchen, and a well-equipped kitchen counter features dual sinks. Natural light filters through the window, illuminating the warm wood cabinetry.
Campervan/RV in Lake Placid
5 out of 5 average rating, 5 reviews

Luxurious RV in a resort, Lake Placid Florida

Enjoy the lovely setting of this romantic spot in nature! RV is located in Camp Florida Resort and has a lot of amenities: heated pool, Pool and ping pong table, tennis court, shuffleboard, pedal boat, kayaks... The rv is spacious and comfortable. Queen bed, fireplace, kitchen and living open layout. Wifi, cable. A barbecue is available to enjoy the outdoors. All you need to spend great time in our beautiful city. Golf courses close by plenty of restaurant and entertainment. No pets allowed....

Top Guest favourite
Aerial view of a spacious ranch-style home surrounded by lush greenery. The property features a winding driveway leading to the entrance, with a vast lawn and diverse trees enhancing the outdoor space. Clear blue skies with scattered clouds complement the serene landscape.
Home in Sebring
5 out of 5 average rating, 14 reviews

Raceway Ranch - Pool, Game Room, 5 Acres, 10 Beds

Raceway Ranch is Sebring’s premiere stay for your group, family or couple that just wants to get away! Located just 1 MILE from the Sebring International Raceway this is the perfect place to stay for your race event or just 5 miles from downtown Sebring where HGTV just featured a massive town reno on “Hometown Takeover”. Float in the pool or spread out in this spacious 3400 sq ft home on 5 acres. Plenty of parking for a trailer as well! Home was remodeled in 2025 and is ready for relaxation!

Top Guest favourite
The exterior of the renovated house is shown, featuring a welcoming front porch with white railings and steps leading to the main entrance. The garage is visible on the right, and landscaping includes shrubs and plants arranged around the property.
Home in Sebring
4.89 out of 5 average rating, 356 reviews

The Good Vibe House

My place is close to the city center and parks. You’ll love my place because of the location, the ambiance, and the people. My place is good for couples, solo adventurers, and business.Half block from Crescent Beach where you can see the sunset or have a cool time in the water,if is not here you can also enjoy the pool at the house.Publix supermarket and others are located just a few blocks and minutes from the house.Fifteen minutes drive to Sebring International Raceway.

Guest favourite
Large glass doors open to a serene lake view, framed by curtains and a cozy seating area. The outdoor space features a well-maintained lawn and a private dock, inviting guests to engage with the calming waters of Lake McCoy.
Home in Lake Placid
4.91 out of 5 average rating, 11 reviews

Lakefront retreat in quaint Lake Placid

Escape to our lakefront retreat, where relaxation meets adventure! Nestled on the shores of Lake McCoy, you are met by lakefront views, a private dock for fishing or boating, and a refreshing pool just steps from your patio. Wake up to sunrises over the lake, sip your morning coffee on the patio, and unwind with a peaceful swim. Located near Sebring Raceway, Orlando, Tampa, and Fort Myers, this is the ideal getaway for adventure seekers and relaxation lovers alike.

Top Guest favourite
Home in Sebring
5 out of 5 average rating, 25 reviews

Lakeview Retreat/ Lake Jackson / Hidden Beach

Home with pool — Walk to Hidden Beach Park. Relax at this peacefully and centrally located 3 bedroom 2 bath home in Sebring. Just a short walk to Hidden Beach Park, this home features a private pool , a beautiful garden and a cozy pergola swing overlooking scenic Lake Jackson. We would love to host you! Whether you are visiting for a weekend or staying longer , we’re here to make your trip to Sebring comfortable, relaxing and memorable. Book your stay today!

Top Guest favourite
The exterior of the house is depicted, featuring a well-maintained landscape with shrubs and flower beds. A wide driveway leads to a welcoming entrance highlighted by a decorative red front door. Lush green trees line the property, providing a serene and inviting atmosphere.
Villa in Sebring
4.97 out of 5 average rating, 109 reviews

Solar Heated Private Pool & Lanai On Golf Course

For a getaway that the whole family will enjoy, stay at this beautiful 3-bedroom, 2-bath vacation rental in Sebring. Spend your days out on the green at the Sun ‘N Lake Golf Club, enjoy a cookout with the family by the pool, or venture into Orlando for a magical day trip with the kids. Whether you’re seeking much-needed R&R or want to take on adventures in the Sunshine State, this bright home will ensure endless days and nights filled with fun.

Guest favourite
Home in Lake Placid
4.96 out of 5 average rating, 26 reviews

Parker Street Palace Pool Home

Where quality time is key! Our Parker Street home is guaranteed to be a returning destination! Take a break and unwind at this peaceful oasis. We are just a canal ride into Lake June, where all the fun memories happen! The infamous Lake June sandbar will keep you coming back! This area is the perfect feel for small town feel and chill vibes the whole time! The best sunsets and the rest is history! Come make our place your favorite spot!

Top Guest favourite
A cozy living area features a pair of beige leather sofas and a comfortable armchair arranged around a wooden coffee table. Natural light enters through two large windows adorned with light drapes. A wall art piece and potted plants add inviting touches to the space.
Apartment in Sebring
5 out of 5 average rating, 17 reviews

Cozy, quiet 2/2 villa with 2 pools!

Located minutes from Sebring Raceway and historic downtown Sebring (as featured on HGTV), enjoy all the amenities of this quiet community tucked into Florida’s peaceful heartland. Relax in the two heated pools on-site, golf at the area course, challenge yourself to a game of pickleball, tennis, or basketball at the courts just down the road, or take a walk around the Spring Lake nature ecopark to catch a nostalgic Florida sunset!

Guest favourite
A modern living area features a comfortable sectional sofa accompanied by a large ottoman. A flat-screen television is mounted on the wall, and a wooden cabinet holds various decorative items. Natural light enters through large windows, framing a view of the outdoor greenery.
Apartment in Sebring
4.93 out of 5 average rating, 14 reviews

Villa in Sebring/ Spring Lake

Unwind in this newly renovated 2BR/2BA villa within Sebring's Spring Lake. Golfers will love the nearby Sebring International Golf Resort, while racing fans can catch the action at Sebring International Raceway. Downtown Sebring and Lake Jackson are just a 12-minute drive, offering dining, shopping, and lakeside leisure. Plus, explore the charming murals of Lake Placid, FL, only a 15-minute drive away.

Guest favourite
The interior of a spacious glamping tent features two beds, each topped with colorful bedding. A table is set with an inviting arrangement, and a rug adds warmth to the floor. Natural light filters through the patterned ceiling and windows, creating a cozy atmosphere.
Farm stay in Venus
4.98 out of 5 average rating, 62 reviews

Glamping+Free Horseback Riding+Petting Farm

Welcome to Animal Lovers Farm, a 20-acre family-friendly sanctuary tucked beneath majestic live oak trees in Venus, Florida. This isn’t just a glamping trip — it’s a heart-warming connection with nature and animals you’ll never forget. Guests enjoy free horseback rides, hand-feeding donkeys, cows, goats, and chickens, and peaceful evenings under the stars by the cowboy pool and firepit.

Guest favourite
A modern farmhouse exterior is displayed, featuring white siding and a metal roof. The entrance showcases double wooden doors, framed by large windows. Lush green grass surrounds the home, accented by neatly arranged landscaping and small shrubs against the backdrop of a cloudy sky.
Farm stay in Lake Placid
4.96 out of 5 average rating, 45 reviews

Family Retreat, Pool, Games & Farm Views, 10 Acres

✦ Why Families Love It Welcome to your family retreat on 10 private acres in Lake Placid, FL. With space for up to 12 guests, this home is designed for relaxation, fun, and togetherness. Parents love the peace and privacy, while kids can jump into the pool, safely explore, ride bikes, and even spot local wildlife like tortoises right in the yard.

Popular amenities for Highlands County rentals with a pool