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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 aerial view of a spacious green landscape featuring a pond and a gazebo surrounded by palm trees. A winding driveway leads through the lush lawn towards Lake Istokpoga, where trees provide shade along the water's edge.
Home in Lake Placid
4.81 out of 5 average rating, 26 reviews

Windy Point Estate

WELCOME TO WINDY POINT ESTATE - Located in a very quiet and serene acers on the bank of Lake Istokpoga. The Estate is an over 6,000 sf /5 bedrooms 5 1/2 bath on magnificent lake front vacation house with breathtaking sunrise views over Lake Istokpoga. Nestled near Lake Placid, FL. This vacation home rests on 4 +/- acres, secluded at the end of the road. Surrounded by lush landscape, a bright green sprawling lawn, majestic trees, a peaceful pond, a gorgeous lake and ample type of birds& Ospreys.

Top guest favorite
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.
Apartment in Sebring
5 out of 5 average rating, 14 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 favorite
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, 105 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

Top guest favorite
Villa in Lake Placid
5 out of 5 average rating, 15 reviews

Enjoy Pool, Billiards, Sauna, Access to the Lake

ENJOY ON-SITE ATTRACTIONS SUCH AS OUR CLAY LAKE AND LAKE JUNE, MULTIPLE WATER ACTIVITIES, AND SURROUNDING PARKS. It's the perfect home for a family getaway or for friends to enjoy. All rooms have a smart TV. This home has a heated pool, sauna, private dock with lake access (bring your boat!), it also has kayak, fishing accessories, a fire pit, grill, a huge backyard, and a billiards room. Everything on Clay Lake: a sandy lake perfect for skiing, tubing, wakeboarding, jet skiing, and fishing.

Top guest favorite
An in-ground pool is surrounded by a screened enclosure, featuring clear blue water that reflects sunlight. Comfortable seating in bright turquoise is arranged nearby, offering a relaxing space for leisure. A wooden fence lines the background, enhancing privacy.
Home in Lake Placid
5 out of 5 average rating, 35 reviews

Lake Clay Getaway

Come relax in this beautifully decorated 3-bedroom 2-bathroom home located around the corner from the Lake Clay boat ramp. The home is equipped with everything you need for a fun get away. Private in ground pool with spacious dining and seating areas outside including a TV, grill and extra refrigerator. King size beds, comfy family room furnishings, large dining room table, and washer and dryer. 1-car enclosed garage available for use during your stay, and plenty of boat and car parking.

Superhost
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, 382 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, 35 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
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, 119 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
An outdoor patio space features a dining table surrounded by four woven chairs, complemented by a striped outdoor rug. A ceiling fan hangs over the area, and views of the pool and landscaped surroundings are visible through the open space.
Home in Lake Placid
4.93 out of 5 average rating, 41 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!

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, 57 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!

Top guest favorite
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, 97 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.

Guest favorite
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, 116 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!

Popular amenities for Highlands County rentals with a pool