Vacation rentals with a pool in Highlands County

5 out of 5 average rating, 4 reviews

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

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....

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.

4.76 out of 5 average rating, 21 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.

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.

5 out of 5 average rating, 21 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.

5 out of 5 average rating, 47 reviews

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

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.

4.89 out of 5 average rating, 341 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.

4.97 out of 5 average rating, 33 reviews

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

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

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.

4.98 out of 5 average rating, 57 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.

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.

5 out of 5 average rating, 15 reviews

Parker Street Palace with access to Lake June

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.

4.95 out of 5 average rating, 19 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!

A sparkling pool is framed by a screened enclosure, offering views of the serene lake beyond. The bright blue water reflects the clear sky, inviting relaxation. A sturdy railing leads into the pool area, enhancing safety while enjoying the outdoor space.

4.82 out of 5 average rating, 17 reviews

Endless Water Daze on Lake June with Seadoo Rental

Welcome to your family or groups favorite, new vacation spot! You’ll experience the peaceful feels of small town life, with breathtaking views of the one and only Lake June in Winter. You have the best of both worlds here, taking a dip in the pool or a dive and ride in the freshwater. With a home theater room to chill out, or a spacious patio area to enjoy refreshing beverages. We can’t wait to have you as our guest!

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.

5 out of 5 average rating, 23 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 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.

4.85 out of 5 average rating, 68 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!

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Popular amenities for Highlands County rentals with a pool

Kitchen

Wifi

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.

4.98 out of 5 average rating, 80 reviews

Relax On Lake Time

KaraRating, 5 stars3 weeks ago

We loved our stay at the lake house. Backyard with pool overlooking the canal was beautiful & peaceful. Kitchen was well equipped for cooking; lots of board game options provided. We took a nice walk after dinner in their neighborhood. Amy was quick to respond with any questions we had. Will definitely stay again at her home when we come to town!

5 out of 5 average rating, 16 reviews

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

Lakeside Retreat

DanielRating, 5 stars1 month ago

We thoroughly enjoyed our stay at Wendy’s place! It could not have been more perfect for us. As soon as we walked in, we felt right at home. The house was spacious, beautifully decorated, light, and airy. The pool was a wonderful bonus, as was the view out over the lake. We loved the bank of windows at the back of the house that brought the outside in. In fact, we have already recommended Wendy’s place to our family for when they come to visit Avon Park.

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.

4.86 out of 5 average rating, 28 reviews

Lake June-Pool Oasis on the lake- Boat Dock

TravisRating, 5 stars2 weeks ago

The listing was accurate with both the pictures and the description. The pool was in great shape and we enjoyed it very much. The beds were comfortable and the kitchen was well appointed with everything we needed. I would stay here again.

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.

4.9 out of 5 average rating, 98 reviews

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

BarbaraRating, 5 stars1 month ago

Thanks for sharing your little piece of Paradise 😊

A large swimming pool with clear blue water is surrounded by a spacious deck. Lounge chairs and umbrellas are positioned along the deck, providing ample seating. Lush greenery and trees frame the area, contributing to a serene outdoor setting.

4.76 out of 5 average rating, 21 reviews

Pool Home off Lake Huntley

JessicaRating, 5 stars3 months ago

Had a great stay. Very clean in every room. Bed was comfortable to sleep. Quiet street as well. Pool was crystal clear to use even though it was still a little too cold to swim in (though we could sit on the edge to keep cool). Would definitely stay here again when we come back to the area.

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.

4.98 out of 5 average rating, 63 reviews

Private Old Florida Lake House Retreat

LauraRating, 5 stars1 week ago

We had a wonderful time and a great family reunion in this beautiful home. Every bedroom, bathroom and all common areas, including a terrific kitchen where immaculately clean and well appointed. The outdoor pool patio area was large and comfy with an outside kitchenette that took care of beverages and provided a grill for feeding our group. Our boat was easily tied up to a large dock, which also provided fun for the younger kids who enjoyed swinging into the lake. Watching the sunrise and set from the comfort of the screen patio was another treat. There was plenty of room for our family of 14 and God willing we’d love to return!

A newly added screened enclosure opens to a spacious area featuring modern outdoor furniture. A dining table with chairs is visible, alongside a lounge seating arrangement. Large glass panels provide a view of the lush golf course landscape beyond, with ample natural light enhancing the space.

5 out of 5 average rating, 18 reviews

Florida's sun and golf living!

BarbRating, 5 stars4 months ago

Tony was very responsive with 2 issues, the thermostat and an ironing board. He quickly responded to our concerns. The unit was clean, comfortable and very well located for our purposes. Plenty of linens, and things you need when you first arrive were provided. The washer and dryer were difficult to understand - while like every other appliance it was easy to turn them on but they didn’t automatically turn off. The dryer was extremely slow. A great tv, a super patio, comfy furniture. We enjoyed our stay and will eagerly return!

A swimming pool is framed by a tiled deck and shaded by a thatched-roof pavilion. Lounge chairs are positioned around the pool area. A bright blue building is visible in the background, contributing to a relaxing atmosphere.

4.95 out of 5 average rating, 22 reviews

Peaceful Home at Sebring Square 130

RyanRating, 5 stars1 month ago

Mark's place was perfect for my coworkers and I and we hope to stay again next year!

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Condo rentals with a pool

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.

4.96 out of 5 average rating, 45 reviews

Downtown Lakefront Condo with stunning sunsets

BeckyRating, 5 stars2 months ago

The condo was nicely updated and well equipped. Trevor was the best host we have had - very helpful. He makes a great ambassador for Sebring, which is like a taste of a quiet, southern hometown.

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.

5 out of 5 average rating, 24 reviews

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

chrisRating, 5 stars10 months ago

I stayed here for an event at the Sebring International Raceway, and it couldn’t have been more convenient! will book again next year

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.

KellieRating, 5 stars1 month ago

New place to stay

Golf course beauty

Place was exactly as pictured. George reached out to answer any questions and tell us how to get in. The place was spotless. Had K cups, creamers and sugars available. Kitchen also has a regular brewer and filters available. It was well stocked and fridge had working ice and water dispenser. There were small toiletry starters available in the bathrooms. Nice handhelds in the showers. Extra towels and linens available. Only used master bed - it was a king size and very comfortable. The living room couch was huge and comfortable. We also enjoyed sitting on the balcony on the sofa out there. Would 100% rent from him again if it’s available!