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Vacation rentals in Winter Haven

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Top-rated vacation rentals in Winter Haven

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

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A dining area features a wooden table surrounded by four chairs, complemented by a television mounted on a textured wall. Large sliding glass doors provide natural light and access to a balcony, with views of greenery outside.

Apartment in Florida Center

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.

A screened patio is featured with a private hot tub, inviting seating options, and a small dining area. The view showcases a serene lakeside with lush greenery and soft evening lighting, creating a relaxed space for outdoor enjoyment.

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.

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.

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.

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.

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!

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.

A light and airy living area features a comfortable sectional sofa and a stylish armchair. A large television is positioned on a media console, and bright windows provide ample natural light. Decorative artwork adorns the walls, enhancing the inviting atmosphere of the space.

Townhouse in Kissimmee

4.85 out of 5 average rating, 378 reviews

GORGEOUS 3BD RESORT, CLOSE TO DISNEY

Search no more ! this beautiful townhome has everything you're looking for. our number one priority are the guest because we want them to have a memorable experience that would last a lifetime. very close drive to disney, restaurants, supermarkets, souvenir shops, highways! Gorgeous newly renovated suite w/ fully equipped kitchen & all the essentials sitting in a cozy townhome w/ pool, hot tub, kids pool, clubhouse w/ gym, bbq area, free parking in front of the unit.

A serene pathway, lined with lush greenery and mulch, winds through manicured landscaping towards a gazebo overlooking a tranquil lake. A fountain emits gentle sprays of water in the distance, complementing the peaceful surroundings.

Townhouse in Kissimmee

4.94 out of 5 average rating, 188 reviews

Beautiful family home near all attractions.

Beautiful, spacious and impeccable townhome close to all parks and entertainment with resort amenities. We follow Airbnb's enhanced cleaning protocol, which was developed with expert guidance. Here are a few highlights: *We sanitize high-touch surfaces, down to the doorknob. *We use cleaners and disinfectanst approved by global health agencies, and We wear protective gear to help prevent cross-contamination. *We clean each room using extensive cleaning checklist.

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 *

Townhouse in Kissimmee

4.87 out of 5 average rating, 115 reviews

♥Disney-3 Miles from ♥Private HotTub ♥to Top♥ Resort

Our gated-community townhouse offers a resort feeling with all the comforts of home, peaceful & quiet, yet central to Disney, Old Town, and all major attractions. After an exciting family day, relax in your private patio hot tub and enjoy the nature, or soak up some sun poolside at the resort. Fun for adults and kids of all ages! Also enjoy the resort tennis courts, pool table, gym, restaurant, and poolside snack bar! NO RESORT FEES! FREE PARKING!

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

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!

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Winter Haven vacation rentals

Laptop-friendly workspace

Stay near Winter Haven's top sights

LEGOLAND Florida Resort513 locals recommend

LEGOLAND Florida Water Park104 locals recommend

Legoland station88 locals recommend

Winter Haven Hospital4 locals recommend

Harborside25 locals recommend

Harry's Old Place17 locals recommend

Home rentals in Winter Haven

A vibrant water play area features a colorful pirate ship surrounded by palm trees and outdoor lounge seating. A slide extends from the ship into a shallow splash zone, inviting family fun. Bright umbrellas provide shade in the background, enhancing the lively atmosphere.

Home in Davenport

5 out of 5 average rating, 18 reviews

New Family friendly townhome.

A modern living room features a large, wall-mounted flat screen TV displaying a scenic image. The space is designed in neutral tones with light-colored tile flooring and a cozy area rug. Large sliding doors offer access to an outdoor seating area.

Home in Kissimmee

4.92 out of 5 average rating, 133 reviews

5 Bdrm (sleeps 13), free water park,closeto Disney

A spacious dining area features a long table set for meals, accompanied by elegant chairs. Soft lighting illuminates the space, enhancing its modern design. A staircase is visible, leading to upper levels, while a well-equipped kitchen can be seen in the background.

Home in Osceola County

4.83 out of 5 average rating, 12 reviews

The Villa Retreat / near Disney

The living room displays a comfortable seating arrangement with a dark sofa, two green chairs, and a small ottoman. Light streams through sheer curtains, enhancing the space, which features neutral walls and a wood-look floor. A TV is mounted on the wall across from the sofa.

Home in Orlando

4.74 out of 5 average rating, 259 reviews

Cozy Home Airport 14 mins Universal 20 mins

The collage showcases the townhouse's interior and amenities: a modern kitchen with dark countertops, a comfortable living area with a sofa and TV, the inviting community pool area with palm trees, and a close-up of the private hot tub, highlighting its bubbling water and easy access.

Home in Kissimmee

4.79 out of 5 average rating, 34 reviews

Minutes from Disney 3BR 2.5BA Townhome w. Hot-Tub

The entrance opens to a bright living area featuring light grey walls and marble-like flooring. Artwork depicting vibrant characters adorns the walls. A ceiling fan is visible above a seating area, and large windows allow natural light to fill the space.

Home in Kissimmee

4.82 out of 5 average rating, 34 reviews

Dream staying in Orlando, FL

The entrance of a gated community is framed by tall palm trees against a clear blue sky. Decorative stone pillars mark the entryway, with lush greenery and vibrant landscaping visible along the driveway. Cloud formations add texture to the scenic backdrop.

Home in Davenport

4.83 out of 5 average rating, 101 reviews

Family Home Gated 10 Beds Pool Disney 7 miles.

A private screened-in pool area features a sparkling blue pool surrounded by comfortable lounge chairs. A hot tub is positioned nearby, with a shaded seating area visible at the back. The space is complemented by bright sunlight and a clear blue sky.

Home in Kissimmee

4.59 out of 5 average rating, 71 reviews

Disney 4 bed 3 bath Pool Hot Tub HP

Other great vacation rentals in Winter Haven

Home in Davenport

4.84 out of 5 average rating, 32 reviews

Solterra discount slps 18/7 bdm/GR/pool/spa5485

An outdoor space features a spacious pool surrounded by a sunbathing area. A covered seating area offers shade under a large umbrella, while palm trees add a touch of greenery. The screen enclosure provides protection while allowing for natural light and fresh air.

Home in Kissimmee

5 out of 5 average rating, 3 reviews

Dream vacation, near Disney

Home in Davenport

4.76 out of 5 average rating, 68 reviews

Vacation home

Home in Davenport

5 out of 5 average rating, 5 reviews

New! Windsor Island Resort with pool by Disney 03

A large swimming pool is surrounded by lush palm trees and sun loungers, offering a refreshing escape. The clear blue water reflects the sky, with steps leading into the pool area. A spacious deck provides ample space for relaxation and enjoyment under the sun.

Home in Davenport, Orlando

4.86 out of 5 average rating, 36 reviews

Orlando Retreat: Cozy Escape for Magical Holidays

Top guest favorite

A colorful water play area features a wooden pirate ship with multiple water features, including a large water bucket and a slide. Stairs lead up to the main deck, surrounded by a splash area, offering a playful environment for children.

Home in Davenport

4.96 out of 5 average rating, 25 reviews

Pelican Escape

A docking area extends into the water, featuring a wooden platform with various kayaks neatly arranged. A gazebo provides shaded seating, and a manicured green lawn complements the serene water view under a clear blue sky.

Condo in Kissimmee

4.9 out of 5 average rating, 120 reviews

D-Gated Resort-5 miles to Disney-2 FREE Water Park

Home in Four Corners

4.88 out of 5 average rating, 16 reviews

DisneyVacationHomeLazyRiver9021

Quick stats about vacation rentals in Winter Haven

Total rentals
450 properties
Total number of reviews
17K reviews
Family-friendly rentals
260 properties are a good fit for families
Pet-friendly rentals
140 properties allow pets
Rentals with a pool
150 properties have a pool
Rentals with dedicated workspaces
250 properties have a dedicated workspace

Frequently Asked Questions

Where should I stay in Winter Haven?
Make yourself at home in Winter Haven by choosing from our most frequently booked neighborhoods. We have over 250 vacation rentals in Florence Villa, over 250 vacation rentals in Downtown Winter Haven, and over 310 vacation rentals in Eagle Lake.
Are there vacation rentals with a dedicated workspace in Winter Haven?
Yes! Work meets play with ease at over 250 vacation rentals in Winter Haven featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in hotel rentals in Winter Haven?
Experience the best of Winter Haven with our hotel rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Winter Haven?
Four-legged friends are welcome in Winter Haven. Choose from more than 140 vacation rentals for guests traveling with pets.
Are there Winter Haven vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 150 vacation homes with pools in Winter Haven, available on Airbnb. Make a splash and soak up the sun in style!
Do hotel rentals in Winter Haven have wifi?
Absolutely! We offer over 30 hotel rentals with wifi in Winter Haven. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winter Haven have a bbq area?
Absolutely! We offer over 50 house rentals with a bbq area in Winter Haven. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winter Haven have a gym?
Absolutely! We offer over 20 house rentals with a gym in Winter Haven. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winter Haven have self check-in?
Absolutely! We offer over 80 house rentals with self check-in in Winter Haven. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Winter Haven?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a gym, over 50 homes with a bbq area, over 290 homes with wifi, over 80 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore