Vacation rentals with a pool in Highlands County

4.83 out of 5 average rating, 23 reviews

Luxury Lakefront | Private Dock | Pool & In-ground

Welcome to a luxury lakefront retreat overlooking the breathtaking waters of Lake Carrie. Spend sun-soaked days on your private dock & swimming beach, unwind in the pool (Pool & In-ground Spa can be heated for $75 per night), or dive into adventure with the water trampoline, rope swing, kayaks, paddleboards & all beach essentials. Enjoy sunset dinners on the outdoor patio, grill in the full outdoor kitchen, gather around the firepit, & end the night with laughs in the game room. Designed for unf

FamilyLocationOutdoor spaces

5.0 out of 5 average rating, 15 reviews

Home in Sebring

Private Lakefront Retreat Pool Spa Tiki

Escape to your own private lakefront oasis in Sebring. Spend the day floating in the pool, unwinding in the barrel sauna, or soaking in the hot tub as the sun sets over the water. Grill and dine beneath the tiki hut, gather around the fire pit under the stars, and relax in the expansive backyard designed for connection and serenity. Inside, a cozy layout with barn doors offers comfort and flexibility for families or groups. With so much to enjoy right on the property you may never want to leave.

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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.

4.96 out of 5 average rating, 113 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

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Superhost

An aerial view of a spacious green landscape featuring a pond and a gazebo surrounded by palm trees. A winding driveway leads through the lush lawn towards Lake Istokpoga, where trees provide shade along the water's edge.

4.81 out of 5 average rating, 27 reviews

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.

LocationFamilyGrill

5.0 out of 5 average rating, 17 reviews

Villa in Lake Placid

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.

ValueLocationHeating

4.93 out of 5 average rating, 14 reviews

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

LocationFamilyNearby

4.89 out of 5 average rating, 390 reviews

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

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.

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4.98 out of 5 average rating, 126 reviews

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

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.

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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.

4.91 out of 5 average rating, 44 reviews

Parker Street Palace Pool Home w/LK June Access

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!

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5.0 out of 5 average rating, 51 reviews

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

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!

ValueLocationKitchen

4.89 out of 5 average rating, 122 reviews

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

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!

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A screened-in patio area features a circular table surrounded by four chairs, overlooking a heated swimming pool. Lush greenery and flowering plants are visible in the background, enhancing the serene atmosphere. The clear blue water of the pool reflects the surrounding nature.