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Featured Winter Haven Villas

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Near Disney Dream Home With Pool

Near Disney Dream Home With Pool

4.0 out of 5.0 4622 Terrasonesta Drive, Davenport, FL
1/5
(1 Reviews)
This villa features an outdoor pool and an indoor pool. Enjoy the fitness center and perks like free self parking and free WiFi. A garden and barbecue grills are also provided.
 
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Belfry Villa #230922 - 5 Br villa

Belfry Villa #230922 - 5 Br villa

4.0 out of 5.0 478 Belfry Drive, Davenport, FL
An outdoor pool is featured at this villa, along with free WiFi in public areas.
 
$239
Villa Near Walt Disney World Resort and Seaworld With 52 Holes of Golf

Villa Near Walt Disney World Resort and Seaworld With 52 Holes of Golf

Winter Garden, FL
This villa features an outdoor tennis court and a spa tub.
 
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Disney Area 3 Bedroom / 2 Bathroom Emerald Island Resort

Disney Area 3 Bedroom / 2 Bathroom Emerald Island Resort

Kissimmee, FL
This villa features an outdoor tennis court and a fitness center. A spa tub is also provided.
 
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'pluto's Pad' - Spacious Villa With Large Pool on Disney's Doorstep

'pluto's Pad' - Spacious Villa With Large Pool on Disney's Doorstep

Kissimmee, FL
A garden is available at this resort.
 
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Quiet and Inviting - 4bed Town House in Regal Palms #4rp908

Quiet and Inviting - 4bed Town House in Regal Palms #4rp908

Davenport, FL
This villa features a fitness center and a spa tub. A garden is also provided.
 
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Aquamarine Hideaway

Aquamarine Hideaway

4.0 out of 5.0 160 Hideaway Beach Ln, Kissimmee, FL
This villa doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the laundry service. There's an outdoor pool on site, and a terrace and a garden are also provided.
 
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Best Price Match Water Park, Lazy River, Arcade, Bar, Gym, Wifi Side by Side

Best Price Match Water Park, Lazy River, Arcade, Bar, Gym, Wifi Side by Side

Kissimmee, FL
This villa features an outdoor tennis court and a fitness center. A spa tub and a garden are also provided.
 
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Luxury 5 Bedroom 3 Bathroom Pool Home Close To Disney

Luxury 5 Bedroom 3 Bathroom Pool Home Close To Disney

Davenport, FL
A spa tub is available at this villa.
 
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Privacy Fence Around Pool - Games Room - TVs Througout - Minutes to Restaurants

Privacy Fence Around Pool - Games Room - TVs Througout - Minutes to Restaurants

Clermont, FL
This villa includes a garden and laundry facilities.
 
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Private Secluded Pool - Less Than 8 Miles to Disney

Private Secluded Pool - Less Than 8 Miles to Disney

Kissimmee, FL
Located in Indian Point, this romantic villa is 1 mi (1.6 km) from Give Kids the World Village and 1.9 mi (3.1 km) from Medieval Times. 192 Flea Market and Green Meadows Petting Farm are also within 3 mi (5 km).
 
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Luxury 5 Bedroom Villa With Private Pool, Game Room, 3 Miles From Disney

Luxury 5 Bedroom Villa With Private Pool, Game Room, 3 Miles From Disney

Kissimmee, FL
A spa tub is featured at this villa, along with a garden.
 
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Winter Haven Villa Rentals

Wake up, stretch, and pad across the bedroom to your kitchen. You’ve got a busy day of exploring ahead, and you’ll face it best with a mug of piping hot coffee in your hand. Look out the window at the rising sun and take a deep breath.

This can be your life if you rent a villa in Winter Haven. Once upon a time, villas were huge Roman buildings owned by the wealthiest citizens. These days, you can still find palatial villas—but there’s smaller, cozier options to choose from as well.

What makes villas so special? First, they offer you and your travel group privacy and space. After a long day of exploring Winter Haven, a villa truly becomes your home away from home. Lay down in one of the bedrooms for a midday catnap, then make use of the fully stocked kitchen and craft a culinary masterpiece to serve up on the private patio. Your companions will be talking about it for years to come.

Do you want to really treat yourself during your time in Winter Haven? Go for it. Luxury villas will make you feel like a million bucks as you sip champagne on a balcony, or cozy up with your someone special and take in the classy artwork. Put that big marble tub to good use. The more fragrant bath salts, the merrier!

At Travelocity, we offer the vacation villa options you want, with a number of villas available for rent in Winter Haven. Get the most out of your time in this fascinating city, wise wanderer, and browse our available villas today.

Top Trending Hotels in Winter Haven

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$59
Winter Haven Gardens Inn and Banquet Center

Winter Haven Gardens Inn and Banquet Center

2.5 out of 5.0 1150 3rd Street SW, Winter Haven, FL
Situated in Winter Haven, this hotel is within 1 mi (2 km) of Indigo's Family Fun Center and Chain of Lakes Park. Lake Conine is 2.8 mi (4.6 km) away. Winter Haven Station is 16 minutes by foot.
 
$81
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2.0 out of 5.0 1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
Situated in the business district, this motel is within a 15-minute walk of Indigo's Family Fun Center and Chain of Lakes Park. Lake Conine is 2.9 mi (4.7 km) away. Winter Haven Station is 14 minutes by foot.
 
$144
Holiday Inn Winter Haven

Holiday Inn Winter Haven

3.0 out of 5.0 200 Cypress Gardens Boulevard, Winter Haven, FL
Located in the heart of Winter Haven, this hotel is within a 15-minute walk of Chain of Lakes Park and Indigo's Family Fun Center. Legoland Florida and Lake Conine are also within 6 mi (10 km). Winter Haven Station is 14 minutes by foot.
 
$71
Econo Lodge

Econo Lodge

2.0 out of 5.0 5665 Cypress Gardens Boulevard, Building b, Winter Haven, FL
Situated in Winter Haven, this hotel is 0.4 mi (0.6 km) from Legoland Florida and within 6 mi (10 km) of Chain of Lakes Park and Indigo's Family Fun Center. Cypresswood Golf and Country Club and Eagle Ridge Mall are also within 9 mi (15 km).
 

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.