Holiday rentals with a pool in Highlands County

Cozy Farm House

Unwind and make lasting memories at this peaceful farmhouse getaway. This spacious 3-bed 2 bath comfortably sleeps everyone with 2 queen beds, 2 twin beds, and a sofa bed—plenty of room to relax and recharge. Enjoy a variety of amenities including a game room, basketball hoop, pool/wet bar area, and a cozy fire pit with swings surrounded by nature. Whether you’re lounging outdoors or enjoying indoor fun, this farmhouse is a true hidden oasis. Conveniently located Your countryside escape awaits!

Sunset & Sand Condo on Lake Jackson

Experience Sebring from above at this beautifully updated 10th-floor lakefront condo. Breathtaking sunset views, luxury finishes, and sandy shoreline, where you can truly put your toes in the sand right on Lake Jackson. Walk 3 blocks to Sebring’s historic Circle. This retreat blends upscale comfort with relaxed Florida lake life. Whether you’re visiting for family time, race events, a season, or a peaceful mid-term stay, this home offers everything you need to unwind and make lasting memories.

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.

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.

Rancho La Esperanza in Okeechobee's full wilderness

Relax with family or enjoy solitude in this okeechobee off grid paradise of peace. The land here is full of wildlife and the amenities of this house offers enjoyment with the backyard paintball field set up, the endless pool hot tub pool system in the back yard patios and the entire home able to host a family of 12. nights are incredible, look out towards the stars or bring a telescope to see what you can find high above with less light pollution. See you At Rancho La Esperanza!

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.

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!

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!

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.

Family Retreat, Pool, Games & Farm Views, 10 Acres

✦ Why Families Love It Welcome to your family retreat on 10 private acres in Lake Placid, FL. With space for up to 12 guests, this home is designed for relaxation, fun, and togetherness. Parents love the peace and privacy, while kids can jump into the pool, safely explore, ride bikes, and even spot local wildlife like tortoises right in the yard.