Vacation rentals with a pool in Highlands County

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).

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!

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.

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

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.

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!

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!

Lakeview Retreat/ Lake Jackson / Hidden Beach

Keep it simple at this peaceful and centrally-located home in Sebring. A short walk to Hidden Beach Park. Enjoy this 3 bedrooms two baths house with a pool with a beautiful garden and a wonderful pergola-swing facing Lake Jackson. We are near the race track , Golf courses and beautifully remodeled downtown. Enjoy your stay.

Lakeside Retreat

Relax with the whole family at this peaceful home to stay. Enjoy our over 1800 sq ft home with a pool and large patio while enjoying a beautiful lake front view. The office features a desk and a pull out queen sleeper sofa. Large master bedroom is furnished for comfort with a king Tempur Pedic luxury mattress.