Vacation 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

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.

Camper/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 favorite

An aerial view captures the stunning lake house's layout, featuring a modern design with a gray metal roof. Lush greenery surrounds the property, while the expansive blue lake is visible in the background along with a private dock and boat ramp.

Home in Lake Placid

4.99 out of 5 average rating, 67 reviews

Private Old Florida Lake House Retreat

This extraordinary "Old Florida" luxury living lake house offers large open living spaces with calming views. Grill out on the screened-in back patio, watching the sunset on the private beach while the kids jump off the dock. On chilly nights, get the fire pit going or take a long soak in the hot tub. Whether you’re here to relax, entertain, or get out on the water, we’ve got you covered. Bring your furry friend, he's a part of the family too! (Pet fee required, please discuss before booking).

Top guest favorite

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, 13 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!

Superhost

A white cottage features a wraparound porch with black outdoor seating. The entrance is framed by a low white railing, and the grass leads to a paved area, providing a welcoming approach to the home. Bright clouds fill the blue sky.

Tiny home in Sebring

4.92 out of 5 average rating, 12 reviews

Premium Cottage 1 Bedroom

These pet-friendly rentals include one bedroom with a queen size bed & flat screen cable TV, plus a sleeper sofa to accommodate 4 guests. They come fully furnished with amenities that include a private bathroom, A/C, washer & dryer, linens, basic cable & WiFi to keep you connected. The kitchen provides full appliances with a microwave, coffee maker, cookware & dinnerware. Outside is a covered porch & a concrete driveway for easy parking. All stays over 28 days will be charged electric usage

Top guest favorite

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

5 out of 5 average rating, 55 reviews

Glamping+Free Horseback Riding+Petting Farm

Experience the perfect blend of nature and luxury with our unique glamping tent getaway. Nestled near the Fisheating Creek Wildlife Park with natural springs ...ideal for swimming and kayaking. Explore our 20-acre farm..... horses, miniature ponies, geese, ducks, roosters, chickens, and goats. Enjoy horseback riding for both experienced riders and free lessons for beginners. Collect fresh eggs, feed the animals, grill out, make s’mores at the fire pit, and immerse yourself in farm life.

Guest favorite

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, 353 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.

Top guest favorite

Home in Sebring

5 out of 5 average rating, 23 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 favorite

A spacious living area is highlighted by a sectional sofa adorned with colorful cushions. A stylish lamp stands beside a wooden table, while framed artwork decorates the walls. A dining area with a white table and chairs is visible in the background, complemented by natural light from large windows.

Apartment in Sebring

5 out of 5 average rating, 8 reviews

Sunny Sebring Getaway

Located in the Spring Lake community of Sebring, Florida, this freshly updated 2-bedroom, 2-bath villa offers a comfortable retreat. Enjoy proximity to the Sebring International Golf Resort, featuring two championship courses, and the Sebring International Raceway, home to the renowned 12 Hours of Sebring endurance race. A short 12-minute drive brings you to Lake Jackson and downtown Sebring, where you’ll find a variety of restaurants, bars, and shopping options.

Top guest favorite

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, 105 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 favorite

Home in Lake Placid

4.96 out of 5 average rating, 24 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 favorite

Home in Lake Placid

5 out of 5 average rating, 46 reviews

Lakefront Home w/ Swim Spa & Sunset Views

Lakefront 3BR/2BA retreat on Lake Huntley in Lake Placid, FL! Enjoy a private dock for boating & fishing, a backyard swim spa, a beach, and a huge screened porch with breathtaking sunsets. Play in the spacious fenced yard, swing under the oak tree, or relax by the fire pit. Open-concept living, fully stocked kitchen, and cozy bedrooms make it perfect for families, couples, or groups. Your Florida lake escape awaits!

Guest favorite

Home in Lake Placid

4.86 out of 5 average rating, 85 reviews

Lakehouse Lodge @ Lk Carrie access to Lake June

In a quaint and quiet neighborhood on Lake Carrie, you are only minutes away from town. Lake Placid, as well as Sebring are only 15-20 minutes to the local grocery stores, farmers markets, and shopping plazas. This property is prime for any events such as birthday parties, bridal showers, even a small wedding! There will be a pet fee for one or more pets!