
House vacation rentals in Winter Haven
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Top-rated house rentals in Winter Haven
Guests agree: these houses are highly rated for location, cleanliness, and more.

Luxury Home 4/3 near Disney, 2 Masters
Luxury 4 bedroom home located in a quiet, gated community about 15 miles from Disney World. The travel time to Disney will depend on the traffic but is usually between 30 and 40 minutes. Fully furnished with 2 master King bed suites, one queen bedroom and one bedroom with 2 twin beds. 3 full baths. 5 high definition televisions, high speed Wifi, free long distance phone calls to US, Canada and UK. Large pool and spa. Large game room with many games and activities for children of all ages.

Southern Dunes Villa - Pool - Golf - near Disney
Stunning executive home with a south facing screened in-ground pool overlooking the 2nd hole of the Southern Dunes Golf Course. Only 13 miles from LEGOLAND and 22 miles from WALT DISNEY WORLD, this is the perfect place to relax after a busy day at the parks. Impeccably maintained, our villa features upgraded furniture, electronics, mattresses and flooring. Southern Dunes is a gated golf community that prides itself on the quality of its golf course and the security and beauty of its homes.

Lakefront Home on the Winter Haven Chain O’Lakes!
Completely renovated 2 Bedroom, 1.5 bath home location on beautiful Lake Roy on the Winter Haven Chain O’Lakes. One bedroom on the lower level with a queen bed. Second story with king bed and twin bed. Full bath located upstairs). Comfortably sleeps 5. (Additional guests must be pre-approved). Free boat parking and boat rental available. House is connected to the main home with a private keyless touchpad for contactless entry. Pet friendly with prior approval and pet deposit.

Gorgeous Gem in the Heart of Lakeland
LOCATION, LOCATION! This gorgeous, spacious, newly renovated home is located on one of the most desired and safest streets in all of Lakeland, and steps away from the beautiful Lake Hollingsworth and Trail. Close to the lake, and a short drive to downtown Lakeland, this gem is in the perfect location! This home features zero gravity beds, a gourmet kitchen, smart TVs and WiFi throughout, comfortable sofas with ample seating for entertainment, dining and more. You'll love this place!

Beautiful Lake House Boating Fishing near Legoland
Welcome to The Executive Lake House ten minutes from Lego Land in beautiful Winterhaven, Florida. The brand new rental home sits on a lake and offers a dock, with boats, fishing gear and beautiful views of the lake. The home offers two bedrooms, a , full kitchen and laundry and one full bathroom The backyard has a playground and pool area that is ( not) included at this price point. If wanting an additional charge of 20 dollars per night Will be charged. Let me know at booking.

Fantastic Water Front Home on the Chain of Lakes
We are sharing our dream home with you! This home offers one of the best open layouts in Winter Haven. Great open kitchen with granite counter tops, stainless steel appliances, and numerous appliances. The large TV room features a Samsung smart 65" TV that connects to the Lanai/Pool area. A must see to believe! Numerous pictures provided to allow your mind to wonder. My interaction with you will be based on you. We have keypad entry for your convenience. I am here for you though!

Florida Oasis w/ Pool near LEGOLAND
We have added a modern twist to the design of this 1950's home with all the modern appliances and finishes. This home is nestled in-between 2 lakes among the Winter Haven Chain of Lakes! The backyard is a Florida Oasis of a great pool and pool deck with plenty of fun available with games for you and the kids, or just enjoy laying peacefully in the sun! 2.5 mile drive from Legoland 3.5 mile drive from Downtown Winter Haven with great restaurants and small town unique shops.

Freshly Renovated Home
Cute older house with modern amenities. Located right downtown within a block from the playpark, Lake Wailes lake, walking path, and the historic downtown shopping area. All of the appliances in the home are brand new, as well as the washer and dryer. There is a large TV in the living room, as well as one in each bedroom - each with Roku and Netflix. Each bedroom also has a mini split A/C unit to sleep as cold, or hot, as you like. Parking is in the rear covered carport.

Spacious 3 Bed, 2 Bath Home Near Legoland
Enjoy family vacation in this fresh, clean 3-bedroom, 2-bathroom home. With keyless entry and a private fenced backyard, you'll have everything you need for a comfortable stay. 4 miles from Legoland 1 mile from downtown Locally owned & operated As residents of Winter Haven, we're passionate about sharing our community with you. We're always ready to assist you with any questions or requests during your stay. Book your stay today and discover the charm of Winter Haven!

Legoland Lakehouse w/Pool &New AC
Relax in style in this 100 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

The Dalt Retreat
The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 10 year old Grandson Dalton. It’s a great spot to relax by the in ground pool and fenced in back yard. Enjoy the outside with your family and cookout. We want you to love The Dalt as much as we do. Located in Winter Haven and Central FL area easy to enjoy the local lakes. Also not too far from other central Fl attractions and beaches from East or West coast.

Villa Blanca
Relax with the whole family at this peaceful pool home located off the quiet roads along the higher elevation of the Florida ridge. Propane tank for home generator. In ground pool covered by enclosed screen. Property fronts the old Sun Air Golf course (not active). An active bar and grill still operates in the old country club at the end of the neighborhood. Right in the center of both Legoland and Disney World
Popular amenities for Winter Haven house rentals
House rentals with a pool

Hollingsworth Pool Home

Mickey's Lakefront Villa at Sunset Lakes

Lake Home w/Heated Pool, Dock, Kayaks & EV Charger

Escape to 4 BR~Fountain Retreat

Awesome Vacation Home w/ Private Heated Pool/Spa

La Casita in Kokomo Bay

4BR,Heated Pool,Jacuzzi & Dining Oasis near Disney

Spacious Private Family Home with Pool
Weekly house rentals

Lakeside Bungalow - Winter Haven Chain-of- Lakes

Encanto At Auburndale

Gorgeous Newly Renovated Home

Central Florida Bungalow! 2 Bedroom 1 Bath

Sunset Lakefront Home | Hot Tub, Private Dock

Birthday Bungalow by Legoland

Adult Luxury - Magic for Families!

Blue Cottage On Parker [Downtown Lakeland]
Private house rentals

Bright Home Near Legoland & Lake

Disney Castle Cove (Pool & Community Boat Ramp)

Cozy2BR/2BR Near Legoland & Winter Haven Hospital

Quiet house with pool on a Top golf course

Lake*Walk2LEGOLAND*Pool*Putting Green*Dock*Sunsets

Little Castle on the canal on lake Arietta

Disney Golf Dreamhouse with Pool 20 min to Disney!

Cozy Retreat in the city
When is the best time to visit Winter Haven?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ503 | ﺩ.ﺇ510 | ﺩ.ﺇ514 | ﺩ.ﺇ507 | ﺩ.ﺇ485 | ﺩ.ﺇ477 | ﺩ.ﺇ477 | ﺩ.ﺇ448 | ﺩ.ﺇ422 | ﺩ.ﺇ463 | ﺩ.ﺇ477 | ﺩ.ﺇ514 | 
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C | 
Quick stats about house rentals in Winter Haven
 - Total vacation rentals- Explore 300 vacation rentals in Winter Haven 
 - Nightly prices starting at- Winter Haven vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees 
 - Verified guest reviews- Over 11,560 verified reviews to help you choose 
 - Family-friendly vacation rentals- 200 properties offer extra space & kid-friendly amenities 
 - Pet-friendly vacation rentals- Find 100 rentals that welcome pets 
 - Vacation rentals with a pool- 90 properties feature pools 
 - Rentals with dedicated workspaces- 170 properties have a dedicated workspace 
 - Wi-Fi availability- 290 of Winter Haven vacation rentals include wi-fi access 
 - Popular amenities for guests- Guests love Kitchen, Wifi, and Pool across Winter Haven rentals 
 - 4.8 Average rating- Winter Haven stays are highly rated by guests—averaging 4.8 out of 5! 
Destinations to explore
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Discovery Cove
- Old Town Kissimmee
- Raymond James Stadium
- Disney's Animal Kingdom Theme Park
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Walt Disney World Resort Golf
- Aquatica
- Amalie Arena
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ZooTampa at Lowry Park
