Vacation rentals with a pool in Highlands County

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.

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

Enjoy Pool, Billiards, Sauna, Access to the Lake

ENJOY ON-SITE ATTRACTIONS SUCH AS OUR CLAY LAKE AND LAKE JUNE, MULTIPLE WATER ACTIVITIES, AND SURROUNDING PARKS. It's the perfect home for a family getaway or for friends to enjoy. All rooms have a smart TV. This home has a heated pool, sauna, private dock with lake access (bring your boat!), it also has kayak, fishing accessories, a fire pit, grill, a huge backyard, and a billiards room. Everything on Clay Lake: a sandy lake perfect for skiing, tubing, wakeboarding, jet skiing, and fishing.

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!

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.

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

Luxury Farm Cabana at Ostrich Ranch, Petting Zoo

Escape to the countryside and unwind at our peaceful poolside cabana, tucked away on the farm just minutes from town. Surrounded by lush gardens, friendly animals, and open skies, this is your perfect spot to rest and reconnect with nature. Wake up to the sounds of ostriches, emus, and farm animals, enjoy your coffee under the gazebo overlooking the horses grazing, as evening falls, watch the sunsets paint the pastures in golden light and gather around the firepit for stargazing.

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.

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.

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!

Escape to the Lake: Pool, Peaceful & Great Fishing

A beautiful piece of paradise nestled in between orange groves on over an acre of land, and in your back yard one of the best fishing canals in Highlands county, enjoy fishing right off the doc. Our home is just a hop skip and jump away from a private access lake! Sebring International Raceway is 25 min away, Lego-land a little over an hour, Lake Okeechobee where some of the biggest Bass can be spotted is a short drive away!

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!