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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Superhost

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

5 out of 5 average rating, 5 reviews

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....

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

4.99 out of 5 average rating, 67 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).

Superhost

A white cottage features a wraparound porch with black outdoor seating. The entrance is framed by a low white railing, and the grass leads to a paved area, providing a welcoming approach to the home. Bright clouds fill the blue sky.

Tiny home in Sebring

4.92 out of 5 average rating, 12 reviews

Premium Cottage 1 Bedroom

These pet-friendly rentals include one bedroom with a queen size bed & flat screen cable TV, plus a sleeper sofa to accommodate 4 guests. They come fully furnished with amenities that include a private bathroom, A/C, washer & dryer, linens, basic cable & WiFi to keep you connected. The kitchen provides full appliances with a microwave, coffee maker, cookware & dinnerware. Outside is a covered porch & a concrete driveway for easy parking. All stays over 28 days will be charged electric usage

Top guest favorite

A private Cowboy Pool is surrounded by lush greenery and plants in decorative pots. The pool's clear water glistens under the natural light, providing a serene spot for relaxation. A wooden deck offers easy access, blending seamlessly into the natural landscape.

Farm stay in Venus

5 out of 5 average rating, 55 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.

Guest favorite

A well-maintained pathway made of pavers leads to a welcoming entrance. Lush green plants frame the entrance, adding a touch of nature. The bright yellow exterior and large arched windows enhance the inviting atmosphere. A neatly kept lawn is visible in the background.

Home in Sebring

4.94 out of 5 average rating, 18 reviews

Sebring Garden Retreat

Welcome to our Garden Retreat! This charming escape accommodates up to four guests with it's own private entrance. Included are a Master bedroom with Queen bed and an Efficiency with Full bed, a kitchenette, and a dining space offering picturesque garden views. Roku TVs are in both rooms. Outside, relax in the garden and soak in the serene countryside ambiance. Experience the perfect blend of comfort and natural beauty, where every detail is crafted to make your stay unforgettable.

Guest favorite

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, 352 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, 22 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

A screened-in patio surrounds a solar-heated pool, with comfortable seating arranged nearby. Sunlight reflects off the water, and a large overhang provides shade. The area is accentuated by clear blue skies, enhancing the inviting outdoor space.

Villa in Sebring

4.97 out of 5 average rating, 104 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

Home in Lake Placid

4.96 out of 5 average rating, 24 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!

Top guest favorite

Home in Lake Placid

5 out of 5 average rating, 45 reviews

Lakefront Home w/ Swim Spa & Sunset Views

Lakefront 3BR/2BA retreat on Lake Huntley in Lake Placid, FL! Enjoy a private dock for boating & fishing, a backyard swim spa, a beach, and a huge screened porch with breathtaking sunsets. Play in the spacious fenced yard, swing under the oak tree, or relax by the fire pit. Open-concept living, fully stocked kitchen, and cozy bedrooms make it perfect for families, couples, or groups. Your Florida lake escape awaits!

Guest favorite

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

4.86 out of 5 average rating, 84 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 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

4.89 out of 5 average rating, 104 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!