The Best Resorts to Book in Kissimmee, Florida

Caribe Cove Resort is a calming haven surrounded on three sides by wooded wetlands
Caribe Cove Resort is a calming haven surrounded on three sides by wooded wetlands | Courtesy of Caribe Cove Resort / Expedia
Photo of Susan Barnes
29 November 2021
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Not only is Kissimmee close to the thrilling theme parks of Orlando, but it’s also a terrific jumping-off point from which to explore the natural attractions of Central Florida. Kissimmee is the Gateway to the Everglades, after all. Take an airboat ride, paddle the waterways, fly along zip lines or soar into the air on a hot-air balloon, and do it all from one of the best Kissimmee resorts – bookable on Culture Trip.

Reunion Resort and Golf Club, for the golfing

4.3/5 (982 Reviews)
Balcony with small table at Reunion Resort and Golf Club
Courtesy of Reunion Resort and Golf Club / Expedia
Price Drop
Now from $241 per night

Once you arrive at this expansive resort west of Walt Disney World Resort, you may never want to leave. The large, lush grounds feature three golf courses, six bars and restaurants, 10 pools, a water park, a fitness center and tennis and pickleball courts, so it’s hard to get bored. Choose from one- to three-bedroom villas or three- to 14-bedroom homes if you’re coming with a bigger crowd – all are smartly comfortable and decorated in soft, muted tones.

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Encore Resort at Reunion, for personalized service

4.2/5 (315 Reviews)
Outdoor pool and water slide at Encore Resort at Reunion
Courtesy of Encore Resort at Reunion / Expedia
Price Drop
Now from $351 per night

Guests at the glamorous four- to 13-bedroom residences dotted throughout Encore Resort enjoy personalized service and access to all the amenities you can think of, from a water park and fitness center to bike rentals and restaurants. You can even have the resort chefs prepare a multi-course meal for you and your family in your vacation home. On top of all this, you’re mere minutes from the famous theme parks of Central Florida.

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Gaylord Palms Resort and Convention Center, for a state-of-the-art fitness center

4.3/5 (1238 Reviews)
A boat on a small pond inside a greenhouse at Gaylord Palms Resort and Convention Center
Courtesy of Gaylord Palms Resort and Convention Center / Expedia
Price Drop
Now from $247 per night

Everything you could ever want in a resort destination and more is here, minutes from the Orlando theme parks. Choose from nine stellar restaurants and bars for a sundowner or a steak, work out in the state-of-the-art fitness center or experience complete relaxation at Relâche Spa. Wander the expansive indoor garden atrium on the way to your room; view-wise, choose from the Gulf Coast Tower or the leafy atrium.

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Margaritaville Resort Orlando, for an island vibe

4.4/5 (1991 Reviews)
Pool at Margaritaville Resort Orlando
Courtesy of Margaritaville Resort Orlando / Expedia
Price Drop
Now from $166 per night

Island life is the vibe at this resort, where the light-filled rooms, spacious suites and private cottages all feel coastal, with pretty blue and coral accents. There’s so much dining choice here, but we think you’ll love tucking into shrimp and grits at the Euphoria Fish House. Everything is on your doorstep, so it’s easy to dive into the Island H2O Water Park, or dig your toes into the sand at the beach club; but do leave some time to scream your way around the theme parks just down the road.

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Caribe Cove Resort, for easy access to a fishing lake

4/5 (2 Reviews)
Pool at Caribe Cove Resort
Courtesy of Caribe Cove Resort / Expedia
Unavailable for the next 3 months

You’re not far from the action at this calming resort, but you’ll feel a world away, and are surrounded by wooded wetlands on three sides. The two- and three-bedroom villas offer tropical decor and plenty of outdoor space for sundowners on private balconies. Experience the great Florida outdoors at Old Lake Davenport, a natural freshwater lake where you can try your hand at boating, fishing and paddling.

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Westgate Towers Resort, for the comforts of home

4.1/5 (977 Reviews)
Aerial view of pool at Westgate Towers Resort
Courtesy of Westgate Towers Resort / Expedia
Price Drop
Now from $93 per night

Find all the comforts of home and more in the studios and spacious one- and two-bedroom villas of this resort, decked out with rugs and paintings for a plush, comforting feel. The nearby theme parks offer lots of fun, as does Westgate Towers Resort itself. There’s Shipwreck Island Water Park, for example, complete with splash pad, pirate ship, lazy river and water slides, not to mention a playground, five pools, game room and fitness center.

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  • Star Island Resort and Club, for tennis and minigolf

    4.1/5 (925 Reviews)
    Pool at Star Island Resort and Club
    Courtesy of Star Island Resort and Club / Expedia
    Price Drop
    Now from $104 per night

    This all-suite resort 4mi (6km) from Walt Disney World Resort will relax hyped-up children (and adults) after a fun-filled day out. Retire to suites decorated in natural tones with kitchens and whirlpool tubs, or gear up for more action with a whopping nine tennis courts, two pools, paddle boats, pickleball and minigolf.

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    Mystic Dunes Resort and Golf Club by Diamond Resorts, to be close to Walt Disney World Resort

    4.3/5 (3160 Reviews)
    Grounds and fountains at Mystic Dunes Resort and Golf Club
    Courtesy of Mystic Dunes Resort and Golf Club / Expedia
    Price Drop
    Now from $84 per night

    This huge resort in Celebration is just east of Walt Disney World Resort and sits among rolling hills, lush Florida nature reserves and beautiful tropical gardens. Tee off on the championship golf course or dive into one of the four heated outdoor pools. Condo-style villas come in studio, one-, two- and three-bedroom variations, each with kitchens and balconies for sipping your morning brew in the sunshine.

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    Legacy Vacation Resorts Kissimmee / Orlando, to make s’mores by the firepit

    3.9/5 (1421 Reviews)
    Pool at Legacy Vacation Resorts Kissimmee / Orlando
    Courtesy of Legacy Vacation Resorts Kissimmee / Orlando / Expedia
    Price Drop
    Now from $70 per night

    Stay in a range of guest rooms, mini suites and one- or two-bedroom suites bathed in warm shades of rust and caramel, just minutes from the thrilling Orlando theme parks. There’s plenty of fun to be had on the resort grounds, from multiple sparkling pools and a splash pad to minigolf and a firepit for roasting marshmallows and making s’mores after the sun goes down.

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    Silver Lake Resort, for a full kitchen

    4.4/5 (973 Reviews)
    Pool at Silver Lake Resort
    Courtesy of Silver Lake Resort / Expedia
    Price Drop
    Now from $96 per night

    There’s plenty of room to move at Silver Lake, both in the smart rooms and the one- and two-bedroom condos with cooling white tiles and full kitchens for fixing your family breakfast each morning. An on-site golf simulator will help you perfect your swing before teeing off on one of the local courses, while the three heated pools and kids’ pool are terrific spots for cooling off afterwards.

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