
House vacation rentals in Winter Haven
Find and book unique houses on Airbnb
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. 13 miles from LEGOLAND, 22 miles from DISNEY, 29 miles from UNIVERSAL, 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 & the security & beauty of its homes.

3/2 Great Family Home Near Legoland
Enjoy easy access to Legoland (4 mi) & charming Downtown (1 mi) from this centrally-located home. Designed to make you feel right at home during your family getaway, the whole home is private to you. We are pet friendly! Featuring a kitchen ready to make a home meal, a fully fenced private back yard, keyless entry, & free, ample parking for multiple cars and a trailer. Street parking is also allowed. Locally owned & operated. We are excited to share our city and provide exceptional service

*This must be THE PLACE FL*
Your place away from home! Have fun with the whole family at this unique and stylish place. You'll have everything you need to relax and recharge. It is located less than 10 mins away from Legoland, restaurants and convenience stores. This house offer 3 BR and 2 full BA as well as a fully-equipped kitchen. All bedrooms include TV, dresser, closet and memory foam mattress. The Master bedroom has a queen bed, and the other two bedrooms have full size beds. There is wifi and parking available.

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, private laundry, smart TVs and WiFi, comfortable sofas with ample seating for entertainment, dining and more. You'll love this place!

Awesome Vacation Home w/ Private Heated Pool/Spa
Sunshine living at its best! The Abbey at West Haven is an enclave of exclusive vacation homes. This gem has been totally redesigned and upgraded for your vacationing pleasure and is the IDEAL choice for your next family vacation or getaway in Central Florida. Stores, restaurants and golf courses are all within 5 mins and Disney just 15 mins away. After a long day at the Theme Parks or a round of golf, relax at the private, pool and spa or enjoy a BBQ on the enormous covered patio.

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. This is a mother-in-law suite that is connected to the main home. 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. Dog welcome with prior approval and pet fee. Boat parking at dock. Boat rental available at Central Florida Water Sports. Private entry with keyless touchpad.

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.

Legoland Lakehouse Canoe & Kayak Retreat
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.

Charming Lakefront Cottage with Stunning Views
Welcome to our lake house retreat in Lakeland, Florida. You can enjoy a peaceful getaway with beautiful sunset views and tranquil waters during the evenings, and still visit major cities such as Orlando and Tampa during the day which are less than an hour away. Minutes from Southeastern University, Florida Southern, Lake Hollingsworth, and other attractions in the Lakeland area.
Popular amenities for Winter Haven house rentals
House rentals with a pool

Adult-Only Getaway w/ Mermaid Pool | 18+, Private

Spectacular Waterfront Home in Winter Haven

Luxury Tropical Themed Villa With Lake View!

La Casita in Kokomo Bay

Great Location | Heated Pool | Awesome Design

"Cozy Retreat with something for everyone"

Southern Dunes Golf Vacation Villa

Sweet Sunshine. 4 king beds. Heated pool.
House rentals with a hot tub

Modern 3br home

Beautiful Pool Home With Rear Conservation Views

Luxury Vacay Home w/ Pool 5Br/5Bath near Disney

There is no other place you want to be than here.

Luxurious Golf Front Oasis: Pool, Spa, View&Cinema

Lazy River, Pool, Slide, Cafe / 4 Bedroom Villa

Heated pool/hot tub, near Legoland, Disney,

Stylish Villa Private Pool-SPA Near Parks Disney!
House rentals with free parking

Elegant Golf Course Home in Southern Dunes

Cozy2BR/2BR Near Legoland & Winter Haven Hospital

3 Bedroom House | 2 Blocks from Lake Hollingsworth

Pet friendly Central Florida Bungalow

Winter Haven Waterfront Retreat

Arcade+Pingpong + 10 guests + 11 mil to Lego Land!

Country Blue Getaway by the Ranch Fields

Escape Comfort Property
When is the best time to visit Winter Haven?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$28,663 GYD | G$29,081 GYD | G$29,290 GYD | G$28,872 GYD | G$27,617 GYD | G$27,198 GYD | G$27,198 GYD | G$26,989 GYD | G$26,361 GYD | G$26,989 GYD | G$27,198 GYD | G$30,127 GYD |
| 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 310 vacation rentals in Winter Haven

Nightly prices starting at
Winter Haven vacation rentals start at G$4,184 GYD per night before taxes and fees

Verified guest reviews
Over 11,350 verified reviews to help you choose

Family-friendly vacation rentals
220 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 110 rentals that welcome pets

Vacation rentals with a pool
90 properties feature pools

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wi-Fi availability
300 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
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Key West Vacation rentals
- Rentals with a kayak Winter Haven
- Rentals with breakfast Winter Haven
- Rentals with pools Winter Haven
- Rentals with a washer and dryer Winter Haven
- Family-friendly rentals Winter Haven
- Rentals with a hot tub Winter Haven
- Rentals with outdoor seating Winter Haven
- Fitness-friendly rentals Winter Haven
- Guesthouse rentals Winter Haven
- Rentals with a patio Winter Haven
- Private suite rentals Winter Haven
- Rentals with a fire pit Winter Haven
- Cottage rentals Winter Haven
- Condo rentals Winter Haven
- Villa rentals Winter Haven
- Hotel rooms Winter Haven
- Rentals with a fireplace Winter Haven
- Apartment rentals Winter Haven
- Pet-friendly rentals Winter Haven
- Cabin rentals Winter Haven
- Waterfront rentals Winter Haven
- Rentals with lake access Winter Haven
- House rentals Polk County
- House rentals Florida
- House rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Raymond James Stadium
- Orlando / Kissimmee KOA
- Universal's Volcano Bay
- Give Kids the World Village
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Amalie Arena
- Aquatica
- Camping World Stadium
- Disney's Hollywood Studios
- ICON Park




