Winter Haven Vacation Rentals & Private Rental Homes.
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Vacation Rentals by Owner in Winter Haven Florida -- We have partnered directly with a major provider for By Owner Rentals, and now have the selection and value to offer our visitors searching for places to rent in Florida.
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Start your vacation here!
We proudly partner with VRBO.com, one of the world's most trusted vacation rental platforms. As an official Affiliate, every listing on our site connects you directly to verified owners through secure booking channels. Whether you're looking for a beachfront condo, a pet-friendly cottage, or a pool home near Disney, we make it easy to find the perfect place to stay in Florida.
Lake Hamilton Hideout
This beautiful home provides the perfect setting for a relaxing and rejuvenating vacation in the heart of central Florida. As soon as you step inside, you will be greeted by a bright and spacious living spaces, complete with comfortable furnishings and modern amenities. The large windows throughout the house provide views of Lake Hamilton. Located just minutes from Legoland and situated on the Chain of Lakes our home is the perfect base for exploring all the area has to offer.
The space
Th.......
Lakefront Vacation Home on the Chain of Lakes in Winter Haven
Newly remodeled Lakefront Vacation Home on the Chain of Lakes right next to Winter Haven Municipal Airport across from Brown's Seaplane base. Come and enjoy the beautiful sunrises over the lake.
The house offers wonderful lake views from almost every room with 2 bedrooms, 2 bathrooms (2nd bathroom in the garage), large living room with sleeper sofa in the corner and small desk, a fully equipped kitchen with dining area, screened lanai/porch with outside furniture, large backyard, interne.......
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. With 3 bedrooms and 3 bathrooms, it can accommodate 6 people. Waterski/barefoot/wakeboard, fish, kayak or SUP from your back door. Nearby slalom courses for water skiers, plus a seaplane base! Wa.......
10.0 Star Review
3 Bedrooms
- Sleeps 8
Winter Haven Vacation Rental
Pets Allowed 
Newly remodeled Vacation Home with Saltwater Pool
This "brand-new" home, built in 2010, totally rebuilt and remodeled in 2022, is located in a gated community in the south of Winter Haven, next to Legoland, and features everything you need for a relaxing vacation. Enjoy the sunsets over Round Lake as you sit out in the nice, large, screened pool area with a 14x28 saltwater pool and relax under the stars.
The house offers comfortable space for 6 guests including children. Additional guests and visitors are not permitted.
The house .......
Luxury 3BR Lake House on Quiet Private Lake, with Pool and Hot Tub
3,800 sq ft Executive Vacation Home on a private lake 5 minutes from Legoland and Peppa Pig, and 40 minutes from DisneyWorld, Orlando, Fl. Three large bedrooms, two with king size beds and all with en suite bathrooms, plus living room, family room, dining room, large laundry room, screened pool and hot tub, screened outdoor dining room and BBQ area (complete with large BBQ) and accessories. Also a games room with a pool table and a TV room with a 65" smart TV. This house is beautifully furnished.......
Spacious home, in a quiet neighborhood near LEGOLAND®-just a 12-minute drive
In this cozy town of Winter Haven, you'll find a beautiful 4-bedroom house that's just a short 12-minute ride away from all the excitement of LEGOLAND Florida. Nestled near the serene Chain of Lakes Park and the natural wonders of The Circle B Bar Reserve, this property offers the perfect blend of adventure and relaxation.
As a traveler, you'll delight in the thoughtful amenities that make your stay truly comfortable. Enjoy the convenience of free WiFi, a washing machine and dryer, and a .......
9.2 Star Review
4 Bedrooms
- Sleeps 10
Winter Haven Vacation Rental
Pets Allowed
Luxury Lakefront Retreat | Heated Salt Pool, Dock & Kayaks | Home Theatre & EV Charger
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 a gorgeous patio, outdoor kitchen and heated pool to share with family & friends! The kitchen is full of natural light with three skylights that stream in the Florida sunshine! There is a fabulous patio door that opens to bring the outside in! If you prefer to spend some downtime with the kids by the he.......
Private pool lake house with game room—just 4 minutes from LEGOLAND
4-Bedroom Lake House Near LEGOLAND | Pool • Game Room • Canal Access
Welcome to our 4-bedroom lake house located at the quiet end of a canal leading to Lake Eloise on the Chain of Lakes, just minutes from LEGOLAND. This home is perfect for families and groups looking for space, comfort, and a relaxing Florida getaway close to the action.
Start your mornings enjoying coffee by the pool, listening to the calm surroundings and easing into the day before heading out to the parks or.......
Lakefront Family Retreat | Private Dock, Tiki Bar & Kayaks | Near Legoland
Welcome to Sunrise on Lake Idylwild
Your perfect lakeside getaway awaits on the beautiful Chain of Lakes in Winter Haven, Florida!
This thoughtfully designed and tastefully decorated lakefront home offers something special for everyone in your group—whether you're planning a family vacation, a relaxing retreat, or a mix of both. Situated on scenic Lake Idylwild, this home features a private dock and connects to 18 other lakes in the chain, opening up endless opportunit.......
Lake Rochelle Rental Lakefront
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 environment with quiet neighborhood and preserve across the lake........
10.0 Star Review
3 Bedrooms
- Sleeps 8
Winter Haven Vacation Rental
Pets Allowed
Family-Friendly 2BR Near LEGOLAND with Parking
Welcome to "Nest", a private front-unit duplex in Winter Haven designed for families, couples, business travelers, and guests visiting LEGOLAND Florida Resort, Peppa Pig Theme Park, Downtown Winter Haven, Winter Haven Hospital, and nearby Central Florida attractions.
Guests will see the "Nest" sign at the front of the property. We use the name Nest because this home is designed to be a comfortable place to land, relax, and feel at home during your stay.
This 2-bedroom, 1-bathroom r.......
TRAVELLING PROFESSIONALS ONLY - 3.3 miles to Winter Haven Hospital!
This home is your home away from home. Quiet, clean, full paint job, all new furnishings, Roku TV in both bedrooms, Queen size beds, dresser with mirror, beautiful desk space with desk lamps.2 bedside tables with lamps in each bedroom, bed linens, towels and wash rags, Private full SKY bathroom for each bedroom, Dove body wash and shampoo provided, washer and dryer in home, kitchen with pots and pans, utensils, cups, bowls plates, kettle, dining tables with chairs, gas stove with oven, communit.......
2 Bedrooms
- Sleeps 1
WINTER HAVEN Vacation Rental
Luxury StayComfy at WinterHeaven
Have fun with the whole family at this two bedroom stylish place. Enjoy two comfy queen beds and a sofa-bed, tv 50'' with streaming and channels. Coffee station, all utensils, and appliances. Welcome refreshment, kids coloring books, washer and dryer. Well located at Winter Heaven, Florida. Only five minutes from Winter Heaven hospital, 14 minutes from Legoland , 40 minutes from Disney, and four minutes from Winter Heaven downtown. Many lakes with outside activities, restaurants and shops.
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Hook, Line & Leisure: Lakefront Gem w/ Porch!
2,384 Sq Ft | Dedicated Office | Yard w/ Fruit Trees
Experience Winter Haven’s authentic, diverse neighborhood vibe in this lakeside retreat. Within walking distance, enjoy a nature park, playground, and sports park. Fish for bass or relax on the lanai to witness stunning sunrises, sunsets, and tropical birds in your private, fenced lakeshore backyard. This tastefully updated home also features a fully equipped kitchen. Book your memorable Florida getaway today!
-- THE PROPERTY .......
Beautiful home located in a gated community only 20 miles from LegoLand!
Beautiful 4 bedroom home in gated community. Private heated pool and hot tub* in an awesome outdoor space. Theater room for those down times. There are 2 lakes within a mile for any of those boating and fishing enthusiests. It is a short 40 min drive to Tampa and a 50 min drive to Disneyworld!
*Please note:We can turn pool heater on for an additional $300 a week. Hot tub is always heated to 102 degrees at no extra cost........
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
Welcome to 3BR 2BA Modern Spacious Lake Home 4 Miles to LEGOLAND, a comfortable vacation home located on a peaceful 3-acre lakefront property on Lake Mariam in Winter Haven, Florida.
This listing is for the left-side unit of a duplex. When facing the building from the street, 1724 is the unit on the left. Each unit is separate and private. The shared area guests should expect is the on-site parking area.
The home is a great fit for families, couples, small groups, business traveler.......
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! .......
Luxury Lakefront Retreat | Heated Pool, Theater & Private Dock | Near Legoland | EV Charger
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 to spend some downtime with the kids by the heated.......
Huge Luxury Lake House on the Chain of Lakes near Legoland!
Welcome to your ultimate getaway in Winter Haven! This stunning 5,500 sq. ft. lakeside home offers 5 bedrooms, 5 bathrooms, and an unbeatable blend of relaxation and fun.
The Space:
Bedrooms & Bathrooms: Three bedrooms on the first floor, including a poolside bathroom with a walk-in accessible shower, and two more bedrooms upstairs.
Dining & Cooking: Grill on the pool deck or cook in the fully stocked kitchen, then gather at the oversized indoor dining table. Enjoy your morn.......
9.8 Star Review
5 Bedrooms
- Sleeps 15
Winter Haven Vacation Rental
Pets Allowed
3 Bedroom Cozy Home with the Perfect Patio
Welcome to our family-friendly home! Just a 5-minute walk to the nearest lake and a short 15-minute drive from Legoland, our charming retreat offers 3 bedrooms, 2 bathrooms, a spacious kitchen, and a cozy living room. Fuel up with complimentary coffee from our bar before exploring the nearby attractions. Unwind on the oversized porch, perfect for observing nature. Ideal for creating lasting memories. Book your stay today and make yourselves at home!
The space
Welcome to our charming and fu.......
Winter Haven Retreat w/ Private Pool!
Run, don't walk, to Winter Haven and experience the ultimate vacation at this charming 3-bedroom, 2-bath home. Ideally located, this vacation rental offers easy access to top attractions, like LEGOLAND, Walt Disney World, and Universal Studios. After a day of fun, return home to relax in the cozy living room or take a dip in the pool. With comfortable bedrooms, a full kitchen, and a beautiful backyard, this vacation home is the perfect retreat for those looking to make unforgettable memories.
Cute & Cozy 1 bedroom guesthouse located in Winter Haven FL
The guesthouse Cute & Cozy is separate yet, it is adjacent to the main house (owner lives) and has its own entrance. Located in central Florida, Winter Haven is between Orlando and Tampa; 3 miles from Legoland, 5-10 minute walk from shopping and restaurants on Cypress Gardens Blvd. The Cute & Cozy is also in a great location for Florida's amazing beaches, just under 2 hours east or west........
Lanai & Pool: Elegant Villa in Winter Haven!
WFH Friendly | Lake Access On-Site | 5,100 Sq Ft
Escape to the ‘Water Ski Capital of the World’ at this Winter Haven vacation rental on the Chain of Lakes. This 4-bedroom, 4.5-bath, Chateaux-style home offers stunning fixtures and unique features for a one-of-a-kind stay. Go boating on multiple nearby lakes, visit Disney World and Universal Studios, or opt to stay home and swim in the beautiful lap pool. A blissful escape awaits!
-- THE PROPERTY --
SLEEPING ARRANGEMENTS- Bedroom 1: .......
Lakefront Lego Land Estate
Welcome to the Lakefront Legoland Estate, a spacious 5-bedroom, 4-bathroom pool home set directly on Lake Summit, part of the Winter Haven Chain of Lakes. Just one mile from LEGOLAND Florida and Peppa Pig Theme Park, and an easy drive to all Central Florida attractions, this home is perfect for families or groups looking for space, comfort, and unbeatable lakefront views.
Inside, you'll find over 4,000 sq. ft. of living space thoughtfully designed for comfort and convenience. The open liv.......
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1722
Welcome to 3BR 2BA Modern Spacious Lake Home 4 Miles to LEGOLAND, a comfortable vacation home located on a peaceful 3-acre lakefront property on Lake Mariam in Winter Haven, Florida.
This listing is for the right-side unit of a duplex. When facing the building from the street, 1722 is the unit on the right. Each unit is separate and private. The shared area guests should expect is the on-site parking area.
The home is a great fit for families, couples, small groups, business travel.......
Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Enjoy your stay in this Historic, large, peaceful, fully renovated Manor. This home consists of 5 bedrooms, 3 bathrooms with modern, fully equipped kitchen, butlers pantry, 2 stocked coffee bars new AC, blue tooth speaker, mood lights and more! All rooms are fully furnished for your comfort. Includes a Private, large yard, in a country like setting but has many amenities in walking distance. Lake access with docks and boat launch across the street. This home is near Legoland, Polk State College,.......
Waterfront Winter Haven Home with Dock & Hot Tub!
Your lakeside paradise awaits at this 4-bedroom, 3-bath Winter Haven vacation rental, perfect for your 'Sunshine State' getaway! The home features luxury amenities, including a 26-foot dock, swimming pool, hot tub, gazebo bar, and game room! Spend each day water skiing on Lake Lulu, toasting cocktails on the dock bar, or jumping in the pool! If that’s not enough for you, this house is nestled right amidst the Chain of Lakes, next to Legoland, and near multiple restaurants you can reach by boat.......
10.0 Star Review
4 Bedrooms
- Sleeps 12
Winter Haven Vacation Rental
Pets Allowed
Legoland 3 Bedroom Pet Friendly Pool Home
Bring the whole family to this great place with lots of room for fun. This home is conveniently located only 2.1 miles from Legoland! Completely remodeled home with new soft close cabinets with granite counter tops to porcelain ceramic tile throughout. Every room has smart tvs so you can stream your favorite streaming service. The home has two bathrooms, one with a full tile shower and the other with a tub to take a relaxing bath. Also brand new leather reclining couches in the living room........
7.6 Star Review
6 Bedrooms
- Sleeps 13
Winter Haven Vacation Rental
Pets Allowed