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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Guest favorite

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....

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

A comfortable bedroom features a queen bed with a patterned blanket. A dark wooden dresser includes a mirror and a television mounted above. Soft natural light enters through a window covered with light curtains, and decorative accents complete the cozy space.

Guest suite in Sebring

4.93 out of 5 average rating, 40 reviews

The Orchard Suite of Sebring

Relax at this newly built peaceful retreat in the quiet and central town of Sebring. This one bedroom has it's own private entrance (with a queen bed), one bath with a walk in shower, a love seat in the living room is perfect for 2 adults . It features a stackable washer and dryer and everything to prepare and cook a meal. There are two smart TV's. The one in the bedroom is connected to cable and the living area has the roku channels. Bring your boat too. We are close to lots lakes.

Guest favorite

A fenced outdoor pool area features a clear blue pool surrounded by a screened enclosure, allowing natural light to fill the space. Four blue lounge chairs are positioned beside the pool, providing a spot for relaxation.

Home in Sebring

4.89 out of 5 average rating, 352 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

A screened-in patio surrounds a solar-heated pool, with comfortable seating arranged nearby. Sunlight reflects off the water, and a large overhang provides shade. The area is accentuated by clear blue skies, enhancing the inviting outdoor space.

Villa in Sebring

4.97 out of 5 average rating, 103 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.

Top guest favorite

A sunny outdoor pool area is surrounded by palm trees and features a clear blue pool with poolside lounge chairs. Nearby, white fencing and building exteriors enhance the calm, inviting atmosphere of the space.

Condo in Sebring

4.98 out of 5 average rating, 61 reviews

Sebring raceway/Spring Lake fully furnished villa

Savor this spacious, comfortable, fully equipped 2 bedroom/2 bathroom ranch condo with screened lanai in the quiet Country Club Villas community. Conveniently located just 5 miles from the Sebring International Raceway and Sebring airport. Enjoy one of 2 community pools or take a stroll around the nearby Eco Park. Go fishing on nearby Lake Istokpoga, one of the biggest Bass fishing lakes in Florida, or visit Highlands Hammock State park.

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, 44 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!

Top guest favorite

A charming house is set on a well-maintained lot, featuring light yellow siding and blue shutters. A covered porch provides shade, while landscaped flower beds add color to the exterior. A paved driveway leads to the entrance, offering convenience for guests.

Home in Lake Placid

5 out of 5 average rating, 32 reviews

Edie’s cottage at Camp Fl Resort

Kick back and relax in this calm, very cute one bedroom house complete with full kitchen, TV, WiFi, screened porch and cobblestone patio for relaxation. Located in Camp Florida Resort, the “Hidden Gem” of Lake Placid, offering a heated salt water pool right on Lake Grassy. Enjoy all the boating and water sports. Plenty of parking for your vehicle and boat at the house.

Guest favorite

A heated pool is enclosed by a screened lanai, allowing natural light to illuminate the turquoise water. The surrounding area features a concrete deck, providing ample space for lounging. Lush greenery can be seen in the background, contributing to a serene environment.

Home in Sebring

4.89 out of 5 average rating, 104 reviews

Tortoise Trail Villa, sleeps 7, 2 full baths, minutes from Sebring Raceway.

Have fun with the whole family at this stylish place. Enjoy hours in the heated pool or relax poolside while food cooks on the grill. Relax by a cozy fire on those cooler nights. Take in all Sebring has to offer, including fishing for that big catch on one of many lakes, or catching a race at the Sebring Speedway. Plenty of room for everyone!

Top guest favorite

Home in Sebring

5 out of 5 average rating, 22 reviews

Lakeview Retreat/ Lake Jackson / Hidden Beach

Keep it simple at this peaceful and centrally-located home in Sebring. A short walk to Hidden Beach Park. Enjoy this 3 bedrooms two baths house with a pool with a beautiful garden and a wonderful pergola-swing facing Lake Jackson. We are near the race track , Golf courses and beautifully remodeled downtown. Enjoy your stay.

Top guest favorite

A cozy living area is shown, featuring a red sofa paired with a light wood coffee table. Natural light enters through two windows, illuminating gray walls and tiled flooring. A small dining table is visible, showcasing a simple table setting, while a fan hangs from the ceiling.

Guest suite in Sebring

4.92 out of 5 average rating, 36 reviews

Guest suite w/ private entrance!

This space is the guest suite in a large home. you will have your own private entrance, very spacious bedroom with bath en suite, a quaint living and dining room, new kitchen cabinets and appliances. The pool is not heated, but perfect during spring, summer and fall. The pool bathroom and laundry is shared space.e