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Vacation rentals with a pool in Highlands County

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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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An indoor solar-heated pool is surrounded by a spacious deck within a wooden-beamed room. Large windows provide views of the lake, while casual seating areas are positioned nearby. Brightly colored decor elements add a touch of character to the serene environment.

Home in Lake Placid

4.79 out of 5 average rating, 24 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

A modern pool glows softly in the evening light, reflecting shades of green from underwater lighting. The surrounding patio is spacious with palm trees visible in the background, and glimpses of the lake can be seen just beyond the pool area.

Home in Lake Placid

4.98 out of 5 average rating, 64 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

An aerial view shows a spacious ranch-style home surrounded by lush greenery on a five-acre lot. The circular driveway is visible in front of the house, leading to clear areas for parking. The landscape includes scattered trees and open grassy fields under a bright blue sky.

Home in Sebring

5 out of 5 average rating, 10 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!

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, 49 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.

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, 349 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.

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, 7 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.

An aerial view showcases a rectangular pool surrounded by a secure black fence. A spacious patio with lounge chairs and a dining area complements the pool. The home's white exterior contrasts with the lush green lawn and open fields beyond.

Farm stay in Lake Placid

4.97 out of 5 average rating, 38 reviews

NEW Family Fun 4BR Home & Pool on 10 acres

BRAND NEW HOME Escape to our serene 4-bedroom family retreat on 10 acres in Lake Placid, FL. Perfect for kids to explore, spot tortoises in the yard, and enjoy family bike rides. Located in a horse-friendly community with space for large vehicles, it's ideal for adventure. Relax by the pool or head to nearby parks and lake boat ramps for outdoor fun. The perfect getaway for families to connect, recharge, and make lasting memories in a peaceful, private setting

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, 60 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.

A welcoming corner features two upholstered armchairs with decorative pillows. A round table is positioned between them, and a large mirror reflects natural light. Light curtains frame the window, while a wall shelf displays tasteful decorations above a sign that reads 'welcome.'

Home in Lake Placid

5 out of 5 average rating, 20 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!

A private pool is surrounded by palm trees and lounge chairs, offering a calming outdoor space. The water glistens under a clear sky, and a stone feature enhances the natural appeal of the area. A fence provides privacy around this tranquil retreat.

Home in Lake Placid

4.96 out of 5 average rating, 23 reviews

The Lakeside Retreat - 4/3 W/Pool, Fast Wifi

Welcome to Lakeside Retreat! Nestled in the serene beauty of Lake Placid, Florida, this spacious 4-bedroom, 3-bathroom house offers the perfect escape. Relax by the pool or unwind on the dock overlooking the tranquil lake. Ideal for families or groups, our home boasts modern amenities and cozy furnishings. Enjoy fishing, kayaking, or simply soaking in the breathtaking views. Experience the ultimate lakeside getaway at Lakeside Retreat!

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, 28 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.

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, 101 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!

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Popular amenities for Highlands County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A screened-in pool area features a clear blue pool surrounded by pale tiles. Sunlight reflects on the water's surface, while a hammock and green float add to the relaxing environment. Lush greenery and a wooden fence enhance the serene atmosphere.

Home in Lake Placid

4.98 out of 5 average rating, 83 reviews

Relax On Lake Time

An outdoor pool area is enclosed by a screened lanai, providing a clear view of the sky. Comfortable seating is arranged around the pool, alongside a dining table for outdoor meals. Lush greenery and an expansive lawn create a peaceful backdrop.

Home in Lake Placid

4.94 out of 5 average rating, 17 reviews

Golf Course Getaway

Top guest favorite

A single-story home presents a clean, white facade, with expansive windows allowing natural light. A manicured lawn features greenery and flowering shrubs. A serene lake can be partially seen in the background, framed by trees under a clear blue sky.

Home in Avon Park

5 out of 5 average rating, 19 reviews

Lakeside Retreat

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

4.87 out of 5 average rating, 31 reviews

Lake June-Pool Oasis on the lake- Boat Dock

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

4.91 out of 5 average rating, 22 reviews

Serene & Fun Retreat with Pool

A sparkling pool occupies the foreground, framed by a stone deck. The nearby house features screened enclosures, while lounge chairs are positioned around the pool. Lush greenery and structures can be seen in the background, creating a serene outdoor setting.

Home in Lake Placid

4.84 out of 5 average rating, 77 reviews

Lakehouse Lodge @ Lk Carrie access to Lake June

Top guest favorite

The serene view of Lake Josephine is captured, showcasing a spacious dock with ample seating. Lush greenery surrounds the property, and a well-maintained lawn extends toward the water's edge. The bright blue sky and soft clouds contribute to a tranquil atmosphere.

Home in Sebring

5 out of 5 average rating, 23 reviews

Large Lake Front/Pool Executive Home in Sebring FL

An outdoor area features a fire pit, with flames radiating warmth. A pool occupies the center, reflecting the sunset colors through the screen enclosure. The horizon displays vibrant hues as the sun sets, framed by palm trees and the tranquil waterside setting.

Home in Lake Placid

4.7 out of 5 average rating, 20 reviews

Endless Water Daze on Lake June

Condo rentals with a pool

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

4.96 out of 5 average rating, 45 reviews

Downtown Lakefront Condo with stunning sunsets

The 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

A comfortable living area features dark leather seating and a glass coffee table. A large flat-screen TV is mounted on the wall, while warm light from a ceiling fan enhances the welcoming ambiance. The space opens to a kitchen area, visible in the background.

Condo in Sebring

5 out of 5 average rating, 24 reviews

Condo w/ Screened-in Porch, 1 Mi to Sebring Golf!

A serene view is presented through a screened window, showcasing a vibrant sunset. The sky transitions from bright yellow to soft orange, while palm trees and grassy areas frame the picturesque landscape. The calmness of the surrounding neighborhood can be sensed in the distance.

Condo in Sebring

Golf course beauty

A comfortable living area features leather couches arranged around a coffee table, with a flat-screen TV placed on a wooden stand against a neutral wall. Large windows allow natural light to fill the space, enhancing the relaxed ambiance.

Condo in Sebring

4.75 out of 5 average rating, 16 reviews

Screened Porch + Pool Access: Cozy Sebring Condo

A spacious living area is furnished with a large sectional sofa and coffee table, with a flat-screen TV mounted on a wooden stand. Natural light fills the room through two large windows, and soft neutral colors create a calm environment.

Condo in Sebring

5 out of 5 average rating, 14 reviews

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

Other vacation rentals with a pool

A serene pool area features clear water reflecting palm trees and the sunrise. Lounge chairs are positioned on the pool deck, and a gentle rippling can be seen in the water. A fence encircles the area, offering a view of the nearby lake.

Home in Lake Placid

5 out of 5 average rating, 5 reviews

Cozy Lake House

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

5 out of 5 average rating, 6 reviews

Cozy, quiet 2/2 villa with 2 pools!

The exterior of a tiny home is visible, featuring light yellow siding and a covered porch with railing. A small table and chairs are positioned on the porch. Lush green grass surrounds the home, and palm trees add to the landscape, with cloudy blue skies overhead.

Tiny home in Sebring

4.73 out of 5 average rating, 22 reviews

Tiny home, (116) 200 sq ft

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

5 out of 5 average rating, 8 reviews

Luxury Cabana at Ostrich Ranch, Petting Zoo Safari

The living area features a generous seating arrangement with two brown leather recliners and a sofa, complemented by a light wood coffee table. A large window, dressed with sheer curtains, allows natural light to brighten the space. Decorative elements include wall art and a small plant on the table.

Home in Sebring

5 out of 5 average rating, 4 reviews

Villa2

Home in Lake Placid

4.56 out of 5 average rating, 50 reviews

Lakeside Serenity on Lake June

A spacious pool area is surrounded by lush greenery and tall palm trees. Several lounge chairs are positioned near the water's edge, offering a comfortable spot to relax. The serene lake is visible in the background, enhancing the natural setting.

Home in Sebring

4.85 out of 5 average rating, 41 reviews

The Little Retreat |Solo, Couples & Small Families

Top guest favorite

The screened-in lanai features a clear blue saltwater pool, surrounded by a white deck. Comfortable seating arrangements are visible, along with ceiling fans for air circulation. Bright blue skies and fluffy clouds provide a scenic backdrop, enhancing the outdoor relaxation space.

Home in Lake Placid

5 out of 5 average rating, 14 reviews

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