Vacation rentals in Lakeland-Winter Haven Metropolitan Area

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

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

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Guest favorite

The iconic entrance of Walt Disney World is displayed, featuring colorful banners and characters, including Mickey Mouse and Minnie Mouse. Lush palm trees frame the scene under a bright sky, inviting visitors to experience the magic of the park.

Apartment 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 favorite

Townhouse in Kissimmee

4.8 out of 5 average rating, 250 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 favorite

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 favorite

An open-concept kitchen and dining area features a large island with modern stools and sleek cabinetry. A light-filled seating area includes two armchairs and a small table, with a flat-screen television mounted on the wall. White curtains frame the windows, enhancing the bright atmosphere.

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 favorite

A meandering lazy river is surrounded by lush tropical landscaping, featuring palm trees and vibrant greenery. The clear water reflects the sky, creating a serene atmosphere. Sun loungers are situated along the riverbanks, inviting relaxation in the outdoor space.

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.

Guest favorite

Condo 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.

Guest favorite

An expansive lobby welcomes guests with high ceilings and elegant decor. Tropical plants and soft seating areas create a relaxed atmosphere. Natural light floods the space, highlighting decorative elements and seating arrangements among the vibrant colors of the furnishings.

Cottage in Kissimmee

4.86 out of 5 average rating, 29 reviews

Cottage Retreat 3BR w Free Parking near WDW

Welcome to the Margaritaville Resort 3BR Cottage in Kissimmee! - Spacious living area with a well-equipped kitchen and comfortable bedrooms. - Enjoy relaxing views in a tropical ambiance surrounded by palm-lined streets. - Short drive to Walt Disney World (10 min), Universal Studios (32 min), and SeaWorld Orlando (29 min). - Amenities include flat-screen TVs, high-speed Wi-Fi, outdoor patio, and free parking. - Perfect for creating unforgettable memories with family and friends.

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

Condo 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 favorite

A sandy beach area is shaded by a thatched roof structure, featuring a ping pong table in the center. Surrounding seating includes blue lounge chairs, with hammocks positioned nearby, all set against a backdrop of tranquil water and greenery.

Apartment 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 favorite

A staircase featuring light wooden steps leads to an upper level, surrounded by neutral-colored walls. A door is visible on the left side, while a cozy living area with a large sofa is partially shown in the background, enhancing the welcoming entryway.

Townhouse in Kissimmee

5 out of 5 average rating, 18 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 favorite

Apartment 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 !

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What guests are saying

NEW! The Seaside Retreat (FREE heated pool)

4.99 out of 5 average rating, 85 reviews1 month ago

This home was as clean, if not more, than some of the nicest places, even hotels, that we have stayed at. Updated beautifully, you couldn't convince me that some of the work wasn't completed yesterday, it was immaculate. We traveled with our toddler, and Nancy already had a pack and play, highchair, appropriate sized life vests, and toys. We felt welcomed and comfortable. The pool area is gorgeous and spacious, we enjoyed the heated pool daily. Even on a chilly (66 degree) day, we still swam. A short distance to Tampa, we recommended planning to eat most meals in the Tampa area, as around Apollo Beach we were disappointed by the selection. Not the hosts fault! We would readily stay again, just would have needed to pick up more groceries to cook (publix is close!) or plan better for meals out. We enjoyed the Florida Aquarium in Tampa, the Manatee Observation in Apollo Beach, and even took a day trip to Anna Maria Island. We enjoyed our stay thoroughly and look forward to visiting again.

Home in Apollo Beach

What guests are saying

Your vacation house near Disney! - 7105

4.57 out of 5 average rating, 7 reviews1 month ago

We had a wonderful stay at this Airbnb! The pictures accurately depicted everything, and I was pleasantly surprised by how nice and very clean the home was. My dad, who usually prefers hotels, was initially hesitant about Airbnb, but after experiencing this stay, he absolutely loved our choice. Our family of seven, including a 2-year-old, felt completely at home. The space was comfortable, and the location was perfect—Disney was close by, and having a Walmart nearby was super convenient for any last-minute needs. Although this place didn’t have many reviews when we booked, we took a chance, and we’re so glad we did! Our entire family loved it, and we would definitely recommend it to others.

Home in Osceola County

What guests are saying

Modern Great Villa near Disney & Parks

4.86 out of 5 average rating, 228 reviews3 weeks ago

Have enjoyed Maayan ‘s place a few times now. Its location to Disney makes it easy to get in and out of parks without being in major traffic. The building is set back off main road and feels safe. It has a nice heated pool and hot tub to enjoy on your down time. Unit itself has most things you would need for a short or long stay.

Apartment in Kissimmee

What guests are saying

Fantasy World 2br, Luxury on Wet n Wild #5

4.72 out of 5 average rating, 226 reviews2 weeks ago

We were only in Orlando for a few days during spring break but we had a wonderful time at their condo. It was clean, comfy and we felt right at home. Would definitely recommend staying here and we will definitely stay here again on our next Orlando trip. Much more affordable than staying at Disney and you cant beat having separate rooms and a nice living space with a kitchen to use!

Townhouse in Kissimmee

What guests are saying

Ground Floor Oasis you will never forget

4.91 out of 5 average rating, 119 reviews3 months ago

Excellent stay. Andrew proactively communicated before and during our stay. He touched base right after check in to make sure all was well. Very responsive when we had a couple questions. The unit was exactly as described and very clean. Grounds were quiet and well maintained. Enjoyed a delicious lunch at Tradewinds restaurant. The staff was nice as well. Highly recommend.

Apartment in Davenport

What guests are saying

Pleasure Vacation Rental

4.86 out of 5 average rating, 73 reviews1 month ago

Me and my Husband and our furbaby enjoyed our stay. Very nice and clean house . Neighbors were quiet the area is nice. The pool was nice and clean. We really enjoyed our stay at the house. Easy check in and check out. Alfredo was very friendly a very great host. I would recommend this home if you're in the area and needing a nice place stay.

Home in Kissimmee

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