Holiday rentals in Lakeland-Winter Haven Metropolitan Area

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Lakeland-Winter Haven Metropolitan Area

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Orlando

5 out of 5 average rating, 6 reviews

Enclave byJS Luxury Vacation Orlando

The best vacation in Orlando,Enclave by JS Luxury Vacation is what you are looking for in comfort and luxury!Affordable rates, unlike the competition. Located in the heart of International Dr,close to the main attractions,Fun Spot,Malls,Walt Disney World,Epic Universe and within walking distance to Universal Studios.Free parking,laundry,restaurant,special parking space for those who need a ramp.Balcony in all apartments.Indoor heated pool,gym, jacuzzi.3 m from turnpike1/2 mile from hway 4.Enjoy.

Guest favourite

Townhouse in Kissimmee

4.8 out of 5 average rating, 251 reviews

#5708 Lakefront Oasis,2 MBRs,Priv Spa,Pool,Disney

Stunning LAKEFRONT view with SOUTH exposure for all day SUNLIGHT. MODERN furniture & HARDWOOD floors! Private JACCUZI! 5 SMART TVs & FREE WIFI. 4 BDS (2 with ensuite, one on each floor) & 3.5 BATH. SS appliances, water filter and quartz counter tops. 10 mins to Disney, 15 mins to Sea World, 20 mins to Universal. Walk to Old Town, Fun Spot, restaurants and stores. Uber/Lyft/Lynx bus to Disney. Resort heated pool, water slides, fitness, tennis, restaurant/bar, mini store and 24/7 gate with guard.

Guest favourite

Home in Kissimmee

4.87 out of 5 average rating, 23 reviews

My Disney Villa

Looking for the ultimate vacation spot near Disney Orlando and Epcot? Look no further! Our newly renovated large 5-bedroom Airbnb is just a genuine 12-minute drive away from these amazing parks, Our home features 2 amazing themed rooms, including a state-of-the-art Star Wars and Mickey Mouse rooms that will surely make your kids feel like they're in their own magical world. We also have 3 large adult rooms, each equipped with comfortable beds, a huge pool area with new furniture, 2 dining areas

Guest favourite

Home in Kissimmee

5 out of 5 average rating, 22 reviews

Disney Vacations Oasis

Experience the best of Disney's area with the comfort and luxury of our home. Whether you're here for adventure or relaxation, we provide everything you need for an unforgettable stay. We prioritize your health and safety. Our home undergoes a thorough professional cleaning and sanitization process prior to your arrival, ensuring every surface is spotless and ready for you to enjoy. Great amenities, including lazy river, restaurant, bar, gym and everything you may need during your stay.

Guest favourite

Villa in Kissimmee

4.83 out of 5 average rating, 69 reviews

Home w/ PVT Pool, Game Room & Resort access 2100

Our luxurious 5-bedroom, 5.5-bathroom home boasts a spacious living room with Smart TV, a fully-equipped kitchen and dining room, a cozy upstairs living area perfect for movie nights as well as an air-conditioned game room featuring a pool table and air hockey. Venture to the backyard to find even more amazing features such as a spacious private pool and SPA, sun loungers, a barbecue and a table with 6 seats where you and your guests will be able to enjoy some sun-filled al fresco dining.

Superhost

Home in Osceola County

4.57 out of 5 average rating, 7 reviews

Your vacation house near Disney! - 7105

Imagine this cozy getaway in a lush gated community, just a stone's throw away from the magic of Disney. This vacation home boasts four thematic bedrooms, perfect for hosting your family and friends. Step into the clubhouse, with an amazing bakery. It's the ideal spot for unwinding after a day of adventure in the nearby theme parks. With its welcoming atmosphere and convenient location, this retreat offers the perfect blend of relaxation and excitement for your dream vacation. Book now!

Guest favourite

Apartment in Kissimmee

4.95 out of 5 average rating, 161 reviews

*Sunset Perch: Views, Reunion Resort, XBox, 2Pools

This modern 3-bedroom luxury condo (with an ELEVATOR right to the door) has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

Superhost

Home in Kissimmee

4.88 out of 5 average rating, 56 reviews

Baby Safe w *Indoor PlayGround*

**Property Requires refundable Security Deposit**Close to Disney Parks! Home equipped for baby! Full nursery, double stroller, highchair, packnplay, outlet covers, baby gates, toys, books, bouncy, and more. Kids love the Toy Story indoor playground with ball-pit, trampoline & slide, the fun doesn't stop at Disney! 6 themed bedrooms (3 Kids & 3 Adult themes), 5 baths, appliance stocked kitchen, a movie/game loft w/ 2 queen sofa sleepers, in-ground pool and Jacuzzi with BABY GATE!

Superhost

Apartment in Davenport

4.65 out of 5 average rating, 54 reviews

Paradise near Disney

All you want and need in Florida is located at my beautiful vacation resort. 1300 square feet of luxury for the right price. First floor, largest patio in all units. 2 amazing club houses. 4 heated pools 5 jacuzzis, restaurant, pool side bars, spa, splash pad, tennis courts, basketball courts even a BEACH with dock for fishing, bbq grills with tables, kids playground, amazing scenic walks, pool tables, volley ball, ping pon,convenience store all available in this amazing resort.

Guest favourite

Flat in Davenport

5 out of 5 average rating, 7 reviews

Bahama Bay Resort * Disney Area

Bahama Bay is a Gated Resort just 10 miles from Disney! With 4 Pools * 6 Hot Tubs * A Splash Pad * Shuffleboard * Sandy Beach Area * Tiki Bar Restaurant * Walking Trails & More is a great place for a Vacation! * NO Resort FEE * Parking is FREE! Resort Villa * 2nd floor Villa * 4 Swimming Pools * 6 Hot tubs * White sandy Beach * On-site Restaurant Tiki & Bar * Beach Volleyball * Tennis * Pickle Ball * Basketball * Fishing * Nature Trails *

Top guest favourite

Townhouse in Kissimmee

4.95 out of 5 average rating, 20 reviews

The Best New TownHome in Kissimmee.

Escape to sunny Kissimmee, Florida, and enjoy the ultimate vacation at our stunning Airbnb rental! Located just minutes from Walt Disney World, Universal Studios, SeaWorld, and other top attractions, this home is perfect for creating unforgettable memories. Perfect for families, couples, or groups, this rental combines convenience, comfort, and style in one incredible location. Your dream vacation in Kissimmee starts here—book now to secure your stay!

Guest favourite

Flat in Davenport

4.93 out of 5 average rating, 15 reviews

Hidden Luxury Paradise

Escape to our newly remodeled tropical oasis, just minutes from Disney, Universal Studios, and Orlando’s top theme parks! Enjoy a mix of fun and relaxation with beach vibes, a sandy volleyball court, tennis courts, pools, hot tubs, splash pads, and peaceful lake views. Grab a bite at the on-site restaurant or relax in a fresh space after a thrilling day at the parks. Your island-style retreat in the heart of Orlando is waiting !