Skip to content

Vacation Rentals & Homes in Winter Haven Florida

Book Your Winter Haven Vacation Rental Directly Online Here and Save!

Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Winter Haven, Florida.

The Russell Lake House - Winter Haven Cottage

The Russell Lake House

This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet, and walk-in shower. AC and heat are available. The property has a pool that can be used while onsite. The entire property's back yard is on a lake (lakefront) with a dock. Fishing poles and tackle can be provided upon request for those who want to fish on the dock or from the bank. Ample off street parking, quiet neighborhood .......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Cottage Rentals

Vacation Home

Vibrant Lakeside retreat centrally located - Vibrant Lakeside retreat centrally located - Winter Haven House

Vibrant Lakeside retreat centrally located

Vibrant Lakeside oasis. A water enthusiasts' paradise! Stunning views of the Lake Buckeye the moment you step through the front door. Endless opportunities for fun on the lake. Private, on-sight boat ramp and dock. Centrally located just 10 minutes to downtown Winter Haven. 13 minutes drive to Legoland amusement park. Seven minute drive to Winter Haven Hospital for medical professional. 1 hour drive to either Tampa or Orlando International Airpor.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Lake Hamilton 2950 - Winter Haven House

Newly Listed! Haven Oasis on Lake Hamilton ~ Private Pool & Backyard Oasis ~ Lake Access ~ Theater

Come to Lake Hamilton’s luxurious lake house and let the sunsets take your breath away as you relax and enjoy making memories at our gorgeous Mediterranean home! No detail has been missed with gorgeous travertine tile and crown moulding throughout the home. The kitchen is full of natural light with three skylights that stream in the Florida sunshine! There is a fabulous patio door that opens wall to wall to bring the outside in! If you prefer .......read more

6 Bedroom(s)
4 Bath(s) - Sleeps 13 House Rentals

Vacation Home

Lake Silver 5 - Winter Haven House

Splash into May -10% Discount May 1st - May 31st!

Ready for some Lake with a New Dock & Lego fun - Lake Silver Retreat in the Heart of the City will take your breath away! One moment you are surrounded by shops and restaurants and the next, you have found yourself nestled in this cozy retreat that is tucked away beneath the trees and close enough to touch the water of Lake Silver. Sit back and watch some of Winter Haven's very own Cypress Gardens Ski Team practicing from the backyard or watch .......read more

5 Bedroom(s)
3 Bath(s) - Sleeps 11 House Rentals

Vacation Home

Idylwild - Winter Haven House

Chain of Lakes w Dock & Kayaks ~Sunrise on Lake Idylwild~Legoland 7.5 mi~Disney 30 mi.

Welcome to SUNRISE ON LAKE IDYLWILD! This gorgeous newly renovated and beautifully decorated lake house is located on the Chain of Lakes at Lake Idylwild and is the very definition of lake living. Lake Idylwild connects with 18 of the Chain of Lakes with its own private dock. This stunning lake house offers spacious outdoor areas with beautiful views. If you’d like to bring your own boat or jet skis, there is a public ramp less than 1 mile f.......read more

4 Bedroom(s)
2 Bath(s) - Sleeps 7 House Rentals

Vacation Home

Lake Jessie - Winter Haven House

Bright Waterfront Home on Winter Haven's Lake Jessie

900 Lake Jessie is a rare rental find. It's a bright lakefront home on Winter Haven's renowned Chain of Lakes. This newly renovated, spacious, single story home on Lake Jessie is well equipped, so you can relax and have fun. The home is fully furnished including towels, bedding, kitchenware and laundry. It can accommodate 10 people. Waterski/barefoot/wakeboard, fish, kayak or SUP from your back door. Nearby slalom courses for water skiers, plus a.......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 10 House Rentals

Vacation Home

Vacation Rentals - Winter Haven House

Lake Lucerne way villa

Welcome to Villa Lake Lucerne, located just around 30 minutes from the Disney World Resort and 17 minutes from the LEGO-Land Resort. Just Relax! You will arrive to a brand new home recently built in August, 2018. Boasting 4 bedrooms, 2 full bathrooms, open great room great for the whole family and a huge screened lanai terrace. Fits 8 guests. Free WiFi and cable. Secured entrance with camera in new neighborhood. Resort style pool!.......read more

4 Bedroom(s)
2 Bath(s) - Sleeps 10 House Rentals

Vacation Home

Lake Silver Retreat III - Winter Haven House

Splash into May -10% Discount May 1st - May 31st!

Lake Silver Retreat III is a home with options ~ you can rent it as a 3 bedroom or a 5 bedroom (some holidays exclusions)! If you're ready for some Lake with a New Dock & Lego fun - Lake Silver Retreat in the Heart of the City will take your breath away! One moment you are surrounded by shops and restaurants and the next, you have found yourself nestled in this cozy retreat that is tucked away beneath the trees and close enough to touch the wa.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 7 House Rentals

Vacation Home

Vacation Rentals - Winter Haven House

Charming Lakefront Pool Home - 5 Min to Legoland!

Our 4 bedroom, 3 bath home is also lakefront, making it a perfect spot for large groups to travel together. Enjoy your evenings 5 minutes to LEGOLAND, 30 minutes to Disney and 50 minutes to Busch Gardens/Tampa. The home sleeps seven with one king bed, two queen beds, and one twin. Kitchen is fully stocked with pots, pans, dishes, and silverware. Backyard patio has a dining set and chairs along the pool to enjoy the lakefront views. The driveway .......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 7 House Rentals

Vacation Home

Hamilton House Suite - Winter Haven House

Lake House to be leased with Main house: 2042348

Only 30 min outside Disney world and Universal Studios. 10 min from Legoland Theme and Water Park. Amazing lake front home. Bring your boat and enjoy skiing, boating and fishing from pier. Lake Hamilton is large lake chain with 2,184 total acres. This is a 1 Bed 1 Bath property with Bed: 1 King Bed & Living Room: 1 Queen Pullout Couch. Fully equipped kitchenette, & Laundry room with Washer/Dryer. Can only be rented with Lake Hamilton Ma.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 House Rentals

Vacation Home

Vacation Rentals - Winter Haven House

NEW LISTING! LAKE FRONT, POOL AND GAME ROOM

NEW LISTING! Beautiful home located in Winter Haven, we are in the center of the state which makes it easy to visit all of your Florida vacation spots. LEGOLAND 1/2 a mile, DISNEY 30 miles, BUSCH GARDENS 50 miles, if you would like to visit one of our famous beaches on either coast you are 70 miles to Clearwater Beach.......read more

3 Bedroom(s)
4 Bath(s) - Sleeps 8 House Rentals

Vacation Home

Tropical Cowboy House - Winter Haven House

Charming Home 5 Minutes From Legoland

Peaceful, safe neighborhood, just down the road from Legoland. Relax and enjoy your time in Florida from the back porch under palm trees with views of horse pastures. This 2 bed 1.5 bath home is perfect for a family visiting Legoland. There are queen beds in each bedroom and a pullout queen memory foam mattress in the living room. Fast WiFi and a 4k TV with Netflix are included for your entertainment. The kitchen is fully equipped. The utility.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Paine Drive - House of Paine - Winter Haven House

New Listing! Family Fun Times ~ Pet Friendly ~ 2 miles to Legoland & close to Disney!

Welcome to Winter Haven! Pack up the SUV and bring the family for a fun weekend away! This centrally located 3 bedroom, 1 bath home that sleeps 9 will be perfect for a big family or two who want to spend time at Legoland or the newly opened Peppa Pig Theme Parks! Just a short 2 mile ride to get to the parks and many choices for restaurants and a grocery store as well. The master has a king bed, a second bedroom with a queen bed and a fun doubl.......read more

3 Bedroom(s)
1 Bath(s) - Sleeps 9 House Rentals

Vacation Home

Scroll To Top