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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Top guest favorite
Home in Sebring

Private Lakefront Retreat Pool Spa Tiki

Escape to your own private lakefront oasis in Sebring. Spend the day floating in the pool, unwinding in the barrel sauna, or soaking in the hot tub as the sun sets over the water. Grill and dine beneath the tiki hut, gather around the fire pit under the stars, and relax in the expansive backyard designed for connection and serenity. Inside, a cozy layout with barn doors offers comfort and flexibility for families or groups. With so much to enjoy right on the property you may never want to leave.

LocationFamilyDecor

5.0 out of 5 average rating, 18 reviews
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

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

FamilyLocationLayout

4.97 out of 5 average rating, 116 reviews
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

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.

FamilyLocationGetting around

4.82 out of 5 average rating, 28 reviews
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

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!

ValueLocationSleep quality

5.0 out of 5 average rating, 38 reviews
Top guest favorite
Home in Lake Placid

Lakefront Paradise Heated Pool Boat Dock & Fishing

Lakefront Paradise on 21 Acres w/Private Beach Private Ranch retreat. 5 Bedrooms + 3 Baths Sleeps 12 + Two Sofa Beds -Heated Pool -Private Beach -Private Dock -Fishing & Watersports -Paddle Boat -Kayaking -Paddle Boarding -Billiards Room -Racing Simulator -Feed the Horses & Friendly Goats -Public Boat Ramp (bring your boat) -24' Boat / Pontoon (Available for Rent) #1: King Bed #2: Queen Bed #3: Queen Bed #4: Queen Bed #5: Kids Room Two Bunk Beds (sleep 4) + Two Queen Sofa Beds

LocationFamilyBeach

4.94 out of 5 average rating, 18 reviews
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

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.

ValueLocationCheck-in

4.89 out of 5 average rating, 394 reviews
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

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.

FamilyLocationCheckout

4.98 out of 5 average rating, 131 reviews
Top guest favorite
Home in Sebring

Cozy 1930s Oasis | Private Pool + Vintage Vibe

Private pool oasis in this cozy 1930s Sebring home. Retro-modern design meets historic charm. • Private Pool: Your exclusive outdoor retreat. • Amenities: Fast Wi-Fi & dedicated parking. • Location: Perfect for race week or weekend getaways. Note: As a nearly century-old home, expect authentic charm, natural wood floor creaks, and original details. If you seek sterile, new-build perfection, this isn't for you. If you love character, welcome!

LocationFamilyCheck-in

5.0 out of 5 average rating, 18 reviews
Top guest favorite
A serene lakeside scene features a sandy beach with palm trees swaying gently. Two lounge chairs and a shaded umbrella provide a relaxing spot, while surfboards lie ready for use nearby. A dock extends into the lake, framed by clear blue waters and a clear sky.
Home in Lake Placid

Lake Beach 7 Bedroom, 4 full Bath + 3rd floor play

Experience the beauty of lake life with this 7-bedroom (one is the third floor that does not have a door) lakefront, over 4000 square foot home! Play along the white sandy beach, enjoy the view from the screened-in patio with outdoor kitchen or watch the stars as you take a soak in your own private hot tub on the second floor balcony! This home is newly renovated and perfectly designed to accommodate you and all of your family and friends.

ValueLocationHot tub

4.96 out of 5 average rating, 198 reviews
Top guest favorite
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

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!

ValueLocationLaundry

5.0 out of 5 average rating, 54 reviews
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

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. Work from our peaceful retreat with our super speedy Starlink internet service. 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!

FamilyLocationQuiet

4.89 out of 5 average rating, 123 reviews
Superhost
Home in Sebring

Luxe Lakefront w/ Pool, Pickleball, & Private Dock

Your luxury lakefront getaway awaits with a heated pool, hot tub, pickleball court, and private dock for endless lake adventures. Play corn hole, relax by the fire pit, or dine outdoors with beautiful lake views. Inside, enjoy the pool table and arcade room—perfect for families and groups. Designed for unforgettable memories, this home blends luxury, comfort, and nonstop fun in one incredible waterfront retreat.

FamilyLocationKitchen

4.88 out of 5 average rating, 16 reviews

Popular amenities for Highlands County rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

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

Lake Clay Getaway

LocationValueQuiet

5.0 out of 5 average rating, 43 reviews
Guest favorite
An inviting outdoor space features a sparkling pool surrounded by lounge chairs. The patio area provides access to the house, with large glass doors leading indoors. Colorful pool floats add a playful touch to the serene environment under a clear blue sky.
Home in Lake Placid

Serene & Fun Retreat with Pool

LocationFamilyAccuracy

4.91 out of 5 average rating, 34 reviews
Guest favorite
The screened-in patio features a tranquil pool surrounded by comfortable seating. A patterned rug lies beneath wooden lounge furniture, while views of the lake and sky can be seen through the screens, enhancing the inviting atmosphere of the outdoor retreat.
Home in Lake Placid

Lake June-Pool Oasis on the lake- Boat Dock

LocationFamilyPool

4.86 out of 5 average rating, 64 reviews
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

Parker Street Palace Pool Home w/LK June Access

FamilyLocationAccuracy

4.92 out of 5 average rating, 48 reviews
Guest favorite
Home in Lake Placid

Lake June Pool home – Canal, gaming room, fishing

FamilyCleanlinessQuiet

5.0 out of 5 average rating, 6 reviews
Top guest favorite
A screened-in pool area offers an unobstructed view of the lake, with gentle waves reflecting the sky. The spacious pool is surrounded by a brick patio, featuring a few outdoor chairs arranged nearby for relaxation.
Home in Lake Placid

LAKESIDE ESCAPE, enjoy Pool-Lake-Fish-Kayak-Canoe

LocationValueAccess

4.99 out of 5 average rating, 87 reviews
Top guest favorite
A manufactured home is presented with a covered front porch featuring white railings. Palm trees sway gently in the background. Brightly colored flowers and shrubs frame the porch, enhancing the home's outdoor appeal. A driveway leads to the carport on one side.
Home in Sebring

Peaceful Home at Sebring Square 130

LocationValueDecor

4.96 out of 5 average rating, 28 reviews
Guest favorite
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

Escape to the Lake: Pool, Peaceful & Great Fishing

FamilyLocationPool

4.95 out of 5 average rating, 60 reviews

Condo rentals with a pool

Superhost
Condo in Sebring

Lakefront Luxury | Sunset Views | Walk to Circle

FamilyLocationCondition

4.8 out of 5 average rating, 10 reviews
Top guest favorite
The exterior of a ranch-style condo is displayed, featuring a well-maintained landscape. A palm tree and neatly trimmed bushes line the walkway, which leads to the entrance. The building presents a neutral color scheme with large windows allowing natural light into the living space.
Condo in Sebring

Sebring raceway/Spring Lake fully furnished villa

ValueFamilyPool

4.97 out of 5 average rating, 72 reviews
Top guest favorite
A serene view of Lake Jackson is displayed at sunset, with the sun dipping below the horizon. The water is calm, reflecting the colors of the sky. Nearby, wooden docks extend into the lake, surrounded by aquatic plants.
Condo in Sebring

Downtown Lakefront Condo with stunning sunsets

FamilyLocationWalkability

4.96 out of 5 average rating, 57 reviews
Guest favorite
A modern living area showcases a large flat-screen TV mounted on a light wall. A cozy gray armchair and a wooden media unit are present. An elegant dining table with four chairs is visible, accompanied by a small kitchen area in the background.
Condo in Sebring

Charming Poolside Villa in Sebring

ValueLocationLaundry

4.95 out of 5 average rating, 19 reviews
Guest favorite
Condo in Sebring

Golf Course Beauty

LocationKitchenCleanliness

5.0 out of 5 average rating, 8 reviews
Condo in Sebring

1 Mi to Golf: Sebring Condo w/ Pool Access!

FamilyLocationAccuracy

5.0 out of 5 average rating, 15 reviewsThe exterior of a condo is presented, featuring a two-car garage with dark green doors. A porch area with two chairs is visible near the entrance, surrounded by landscaped grass and shrubs. The driveway is paved, leading to the garage.
Condo in Sebring

Country Club of Sebring Villa

HospitalityWalkabilityComfort

4.67 out of 5 average rating, 3 reviews
Condo in Sebring

Screened Porch + Pool Access: Cozy Sebring Condo

LocationComfortTV

4.76 out of 5 average rating, 17 reviews

Other vacation rentals with a pool

Guest favorite
Villa in Lake Placid

Enjoy Pool, Billiards, Sauna, Access to the Lake

LocationFamilyNearby

5.0 out of 5 average rating, 17 reviews
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

Sebring Raceway & Golf Villa @ Spring Lake w/Pools

FamilyLocationWalkability

5.0 out of 5 average rating, 16 reviews
Guest favorite
An ostrich is prominently featured in the foreground, with details of its distinctive long neck and soft feathers visible. In the background, additional ostriches roam freely across a grassy area framed by trees, under a sky filled with soft clouds.
Farm stay in Sebring

Luxury Farm Cabana at Ostrich Ranch, Petting Zoo

ValueFamilyView

4.93 out of 5 average rating, 40 reviews
Guest favorite
A dining area is featured with a rustic wooden table surrounded by six white chairs. Above the table, a chandelier provides soft lighting, and a large world map is displayed on the wall, creating a welcoming atmosphere.
Farm stay in Lake Placid

Cozy Farm House

LocationValueKitchen

4.95 out of 5 average rating, 78 reviews
Superhost
A single-story house features a blend of light and dark red accents on its exterior. A manicured lawn surrounds the property, leading to a curved concrete driveway with a garage. The sky above showcases soft clouds, hinting at a pleasant daytime atmosphere.
Home in Sebring

Relax, golf and swim at sun n lake retreat

FamilyValueBathroom

4.62 out of 5 average rating, 77 reviews
Guest favorite
A spacious living area is highlighted by a soft sectional sofa, inviting relaxation. A circular coffee table sits at its center, resting on a decorative area rug. A series of landscape photos adorns the wall, while a doorway leads to another room. Natural lighting enhances the warm wood flooring.
Home in Sebring

Country Club Villa - Gator Den

ValueLocationLaundry

4.95 out of 5 average rating, 43 reviews
Guest favorite
The aerial view captures the scenic lakefront setting of the townhouse complex, surrounded by lush greenery. A calm lake stretches into the distance, reflecting the sky, with several boats moored at the private dock, suggesting opportunities for water activities.
Townhouse in Lake Placid

Beautiful Lakefront Townhouse with Pool

FamilyValueDecor

4.84 out of 5 average rating, 98 reviews
Guest favorite
A spacious home with a light blue exterior features a well-manicured lawn surrounded by tropical landscaping. The front porch is highlighted by decorative wrought iron accents. A clear blue sky with scattered clouds creates a bright backdrop.
Home in Sebring

Relaxation Station! Remodeled pool home

ValueLocationHot tub

4.84 out of 5 average rating, 25 reviews

Destinations to explore