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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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Top guest favourite
A well-maintained single-story home is set against a clear blue sky. The landscaping features lush greenery, including palm trees, and the driveway accommodates multiple vehicles leading to a spacious two-car garage.
Home in Lake Placid
4.96 out of 5 average rating, 104 reviews

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

Top guest favourite
Villa in Lake Placid
5 out of 5 average rating, 14 reviews

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.

Top guest favourite
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.
Home in Lake Placid
5 out of 5 average rating, 35 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.

Superhost
Home in Okeechobee
5 out of 5 average rating, 16 reviews

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!

Guest favourite
The exterior of the renovated house is shown, featuring a welcoming front porch with white railings and steps leading to the main entrance. The garage is visible on the right, and landscaping includes shrubs and plants arranged around the property.
Home in Sebring
4.89 out of 5 average rating, 375 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.

Guest favourite
A spacious pool area is surrounded by lush greenery and tall palm trees. Several lounge chairs are positioned near the water's edge, offering a comfortable spot to relax. The serene lake is visible in the background, enhancing the natural setting.
Home in Sebring
4.88 out of 5 average rating, 60 reviews

The Little Retreat |Solo, Couples & Small Families

Our cozy second-floor cabin in Sebring is surrounded by nature and waiting just for you. Enjoy peaceful mornings on the balcony with bird songs, take a break and relax by the shared heated pool, or take in the lake views from the private dock. With fast Wi-Fi, AC, and all the comforts of home, it’s close to lakes, trails, and great local eateries. The perfect spot to unwind, recharge, and feel truly at peace—your home away from home. We will love to host you!

Top guest favourite
The exterior of the house is depicted, featuring a well-maintained landscape with shrubs and flower beds. A wide driveway leads to a welcoming entrance highlighted by a decorative red front door. Lush green trees line the property, providing a serene and inviting atmosphere.
Villa in Sebring
4.97 out of 5 average rating, 117 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 favourite
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.
Home in Lake Placid
4.92 out of 5 average rating, 38 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 favourite
A cozy living area features a pair of beige leather sofas and a comfortable armchair arranged around a wooden coffee table. Natural light enters through two large windows adorned with light drapes. A wall art piece and potted plants add inviting touches to the space.
Apartment in Sebring
5 out of 5 average rating, 41 reviews

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!

Top guest favourite
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.
Home in Lake Placid
5 out of 5 average rating, 39 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.

Guest favourite
Two children are captured in mid-air, joyfully jumping into a pool. The water reflects sunlight, creating a shimmering effect. In the background, a wooden deck extends towards a serene lake, bordered by lush trees and palm plants. Sun loungers are arranged nearby.
Home in Lake Placid
4.83 out of 5 average rating, 109 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 favourite
A modern farmhouse exterior is displayed, featuring white siding and a metal roof. The entrance showcases double wooden doors, framed by large windows. Lush green grass surrounds the home, accented by neatly arranged landscaping and small shrubs against the backdrop of a cloudy sky.
Cabin in Lake Placid
4.97 out of 5 average rating, 58 reviews

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.

Popular amenities for Highlands County rentals with a pool