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Winter Haven Vacation Rentals & Private Rental Homes.

Large selection of Rentals, book your Winter Haven Vacation Rental Home Here and Save!

Many rental properties to choose from, including private Homes, Cottages or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities that will make your Florida visit the perfect getaway.

Rentals by Owner in Winter Haven Florida.

We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of Short Term Rentals to choose from, we now have the selection and value to offer our visitors searching for places to rent in Winter Haven Florida.

Select from the following Rental Properties:

Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!

Winter Haven Vacation Rental Star 4.5 Star Review

Awesome lake house, with a private dock, kayaks, a canoe, a game room with foosball, air hockey/small pool table, an arcade with 100s of games, board games, a yard with hammock swings, games, kid electric car & the lake has boat ramps, so bring your water toys.

This lake is a fishing paradise we have caught crappies, red ears, bluegills, and.......read more

3 Bedrooms - Sleeps 11
Vacation Rental Home in Winter Haven



15% Off ~ Lakehouse with Dock ~ Pristine Lake Water & Close to LegoLand!

Winter Haven Vacation Rental Star 4.8 Star Review

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 yoursel.......read more

3 Bedrooms - Sleeps 7
Vacation Rental Home in Winter Haven



Serenity Retreat, Confidently Clean

Winter Haven Apartment Star 5.0 Star Review

This is a unique 2 story antique building that has been completely renovated and sectioned into 2 small apartments on the 2nd floor. This property was designed with our guest in mind, to offer an oasis of peace, tranquility; geared towards meditation and relaxation. Though we are located only few minutes from restaurants, stores, hospitals, unive.......read more

1 Bedrooms - Sleeps 3
Apartment in Winter Haven



This beautiful lake house has something for everyone!

Winter Haven Vacation Rental Star 4.7 Star Review

The Lake House at 1443 S. Lake Roy Drive on the chain of lakes - At over 5,000 square feet, this two story 5 bedroom, 5 bath home is a great way to escape to the warmth and solitude of Central Florida with friends and family.

Only .7 miles to Legoland, 50 miles from Orlando, less than 50 miles to beaches near Tampa and close to MANY waters.......read more

5 Bedrooms - Sleeps 14
Vacation Rental Home in Winter Haven



Bright Waterfront Home on Winter Haven's Lake Jessie

Winter Haven Vacation Rental

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/bare.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Winter Haven



Lake Lucerne way villa

Winter Haven Vacation Rental

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.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Winter Haven



*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1722

Winter Haven Vacation Rental Star 4.8 Star Review

WELCOME! Lake Mariam Vacation Home (1), is part of a duplex that sits on 2.6 acres of Lakefront Property. There is also a Tiny Home located the duplex, behind this property; but every guest has a lot privacy and there is NO interaction.

If hospitality & quality sleeping accommodation is what you want, our space focuses on that & much more. .......read more

3 Bedrooms - Sleeps 7
Vacation Rental Home in Winter Haven



Lake Rochelle Rental (Lakefront)

Winter Haven Vacation Rental Star 4.9 Star Review

Huge, fenced yard with quaint 3/2 trilevel
house overlooking Lake Rochelle in Northeast Winter Haven. Just
minutes from LegoLand Florida and U.S. 27 and approx. forty minutes
to Disney/Universal/Sea World, our lakehouse is designed to get away
from it all. No smoking please. Great bird watching, fishing, and
boating. Very serene .......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Winter Haven



Modern HouseBoat*AceLoca*4Miles*LegoLand*

Winter Haven House boat Star 4.9 Star Review

Welcome to the SeaRover on Lake Mariam part of the Chain of Lakes! This is a fully furnished newly renovated house boat that is permanently docked. It comes complete with a full kitchen with propane stove and oven, microwave, coffee maker and mini fridge freezer. The living room features a 55" smart tv and a sofa bed that sleeps 1 along with an Al.......read more

1 Bedrooms - Sleeps 3
House boat in Winter Haven



Soak up the charm of this cozy, recently remodel studio.

Winter Haven Apartment Star 4.9 Star Review

This studio is located minutes from Downtown Winter Haven, one of Florida\'s oldest towns. It is a small downtown, that is packed with lots of unique delightful places where you can eat and drink. It’s also a perfect place just to walk around and have a relaxing evening. Its a place you must experience at night!.......read more

1 Bedrooms - Sleeps 2
Apartment in Winter Haven



★2/1★Central★Location★☀2-Mile LEGOLAND&Dining☀

Winter Haven Vacation Rental Star 5.0 Star Review

There’s no better way to experience the beauty of Winter Haven than by sleeping right in the heart of it. “Nest” is situated right in the middle of the city with shopping and dining just minutes away. This modern, two-bedroom home is ONLY 2 miles (7 min drive) from LEGOLAND Florida and Pepa Pig theme parks. It is the perfect place to relax af.......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Winter Haven



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