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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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Top guest favourite
An open-concept living space features a dining table adorned with sunflowers and a cozy sofa. A ceiling fan circulates air, and a large window invites natural light. A TV is visible, along with light blue walls and decor that contribute to a relaxed ambiance.
Flat in Sebring
5 out of 5 average rating, 11 reviews

Sebring Raceway & Golf: Spring Lake Villa w/Pool!

Can you hear that? Your vacation home is calling you. Pack your fishing poles and golf clubs, pickleball paddles, bicycles, and don’t forget your bathing suit! Located in the quiet Country Club Villas community, this freshly painted and newly updated 2 bedroom, 2 bath villa is conveniently located just 5 miles from the Sebring International Raceway and Sebring Regional Airport and less than a mile from the Sebring International Golf Resort. And Bike Sebring is literally right outside your door!

Top guest favourite
A well-maintained single-story home is set against a clear blue sky. The landscaping features lush greenery, including palm trees, and the driveway accommodates multiple vehicles leading to a spacious two-car garage.
Home in Lake Placid
4.96 out of 5 average rating, 104 reviews

Life is better at the Lake.Pool/Spa/Dock/Lake June

This fully equipped pool home is located at the canal to Lake June in Lake Placid, FL. Enjoy quality time, whether it's boating, jumping in the pool, relaxing with a good book, golfing or reconnecting with friends and family. This fully equipped 4 bedroom home, build in 2005 features a screened in HEATED Pool & Spa, boat parking alongside the dock directly at the house, BBQ & more. A Golf Cart available @ additional charge. Close to Golf, shopping, Restaurants and downtown. Full house generator

Superhost
Home in Okeechobee
5 out of 5 average rating, 15 reviews

Rancho La Esperanza in Okeechobee's full wilderness

Relax with family or enjoy solitude in this okeechobee off grid paradise of peace. The land here is full of wildlife and the amenities of this house offers enjoyment with the backyard paintball field set up, the endless pool hot tub pool system in the back yard patios and the entire home able to host a family of 12. nights are incredible, look out towards the stars or bring a telescope to see what you can find high above with less light pollution. See you At Rancho La Esperanza!

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, 372 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 favourite
Home in Sebring
5 out of 5 average rating, 31 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, 116 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 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.
Flat in Sebring
5 out of 5 average rating, 36 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!

Superhost
A newly renovated pool area is displayed, featuring a spacious pool and a separate hot tub. Surrounding the pool is a stone deck with a smooth surface, framed by green grass and trees in the background, creating an open outdoor space under a clear blue sky.
Home in Lake Placid
4.95 out of 5 average rating, 55 reviews

Escape to the Lake: Pool, Peaceful & Great Fishing

A beautiful piece of paradise nestled in between orange groves on over an acre of land, and in your back yard one of the best fishing canals in Highlands county, enjoy fishing right off the doc. Our home is just a hop skip and jump away from a private access lake! Sebring International Raceway is 25 min away, Lego-land a little over an hour, Lake Okeechobee where some of the biggest Bass can be spotted is a short drive away!

Guest favourite
A screened-in patio area features a circular table surrounded by four chairs, overlooking a heated swimming pool. Lush greenery and flowering plants are visible in the background, enhancing the serene atmosphere. The clear blue water of the pool reflects the surrounding nature.
Home in Lake Placid
4.98 out of 5 average rating, 94 reviews

Relax On Lake Time

Waking up to the sounds and sights of nature provides the reset we all need. When you're on lake time, our 3/2 lake home with heated pool, outdoor fireplace, boat dock and the quaintness of main street nearby--gets you there in no time. Whether you'd like to go boating, fishing, birding, golfing or napping--it's all right around you within a few minutes.

Superhost
Two children are captured in mid-air, joyfully jumping into a pool. The water reflects sunlight, creating a shimmering effect. In the background, a wooden deck extends towards a serene lake, bordered by lush trees and palm plants. Sun loungers are arranged nearby.
Home in Lake Placid
4.82 out of 5 average rating, 105 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!

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, 57 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.

Top guest favourite
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
4.9 out of 5 average rating, 117 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!

Popular amenities for Highlands County rentals with a pool