Vacation Rentals & Homes in Winter Haven Florida
Vacation Rentals by Owner in Winter Haven, Florida.
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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
New 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, internet,.......
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 seaplane base! Watch the sunrise from your privat.......
10.0 Star Rating
3 Bedrooms
- Sleeps 8
Winter Haven Vacation Rental
Pet Friendly 
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
This beautiful family-friendly home is ideally located near all of central Florida's attractions. Only a few minutes from Polk Pkwy/I-4, Legoland, Peppa Pig Park, and Bok Tower Gardens. Easy commute to Disney, Orlando, and Tampa. Close to shopping and restaurants. Located in a safe and quiet community.
This home has two living and dining areas that will accommodate large families. The outdoor patio is great for entertaining. The kitchen is well equipped with the appliances and utensils yo.......
9.2 Star Rating
4 Bedrooms
- Sleeps 10
Winter Haven Vacation Rental
Pet Friendly
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 lanai, 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 on Canal to LEGOLAND’s Lake Eloise on the Chain of Lakes, bring your jet skis- there is a small boat ramp across the canal to launch or head to the Marina just a few miles down the road and rent a pontoon boat for the day. Large solor heated/cooled inground pool w/ 55” tv WITH SOUNDBAR on the large pool patio for the family to enjoy. There is also a large pool house full of cool arcade games: Pac Man, Ski Ball, Air Hockey, Darts, Corn hole and plenty of board games. Insi.......
Lakefront Family Retreat | Private Dock, Tiki Bar & Kayaks | Near Legoland
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 from the home at the Lake Cannon Public Park. We h.......
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 Rating
3 Bedrooms
- Sleeps 8
Winter Haven Vacation Rental
Pet Friendly
Family-Friendly 2BR Near LEGOLAND with Parking
WELCOME to our Wakulla Vacation Home (1) “Nest” which is a duplex property. We are a family own business & genuinely hope to tailor our properties to meet our Guest needs. We adhere to a 3 Core Property Standards that we expect; so, you'll always arrive to a home that is Safe, Clean and Guest Ready!
This property is centrally located, 2 mi to dtwn Winter Haven and the Hospital & 2 mi to LEGOLAND & Peppa Pig........
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!
Living up to its city name, this elegant 3-bedroom, 3-bathroom Winter Haven home features the perfect haven for escaping to the warmth. Complete with a welcoming atmosphere and a lakefront yard, this vacation rental is optimized for relaxation and fun. Go fishing on Lake Maude, spend a day at Disney World, and visit the largest LEGOLAND in the world. At day’s end, return to a modern kitchen, an electric fireplace, Smart TVs in every room, and a screened-in porch with serene lake views.
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Beautiful home located in a gated community only 20 miles from LegoLand!
7 year old home in gated community , private pool, heated with heated hot tub all screened in with a awesome outdoor space. theater room, minutes from winter haven, 2 lakes within a mile for boating and fishing needs, 40 min from Tampa and 50 min from Disneyworld. We can turn pool heater on but it is a addition 300 a week. But hot tub is free to people staying there hot tub it heated to 102 degrees........
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724
WELCOME! Lake Mariam Vacation Home (2) is part of a duplex built in 2016 that sits on 2.6 acres of Lakefront Property. If hospitality & quality sleeping accommodation is what you want, our space focuses on that & much more. Rejuvenate from a day of Adventure or Business in our Lakefront property home. ONLY 4 miles from LEGOLAND. Famous Orlando attractions (SeaWorld, Disney/Universal, Airport & Downtown) all w/in an hour drive!.......
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!
Escape to Paradise on the Chain of Lakes! The Lake House at 1443 S. Lake Roy Drive welcomes you to a 5,000 square foot retreat, boasting 5 bedrooms and 5 baths spread across two spacious stories. Nestled in the heart of Central Florida, this luxurious home promises warmth, tranquility, and special moments with your loved ones.
Conveniently located, this lakeside haven is just a mere 0.7 miles away from the thrilling Legoland, 37 miles from the magical world of Disney, and less than 50 mil.......
9.8 Star Rating
5 Bedrooms
- Sleeps 15
Winter Haven Vacation Rental
Pet Friendly
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!
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-bathroom, Chateaux-style home offers imported double French doors that open to a grand marble entry, brass light fixtures, a crystal dining room chandelier, and a floating spiral staircase to make your stay unique. Enjoy access to multiple nearby lakes and boat slips, visit Disney World and Universal Studios, or opt to stay home and swim in the beautiful lap pool.
Lakefront Lego Land Estate
Relax and enjoy the waterfront lifestyle in our beautiful home nestled on Lake Summit in Winter Haven.
Located 1 mile from Legoland and 3 miles from downtown, you will be a short drive away from all the attractions, restaurants, and bars Winter Haven has to offer. This is a perfect location for exploring all of Winter Haven, Lakeland, Tampa, Orlando, Disney World, and Florida Beaches.
This 4 bedroom, 3 bathroom home features 4000 sq. ft of living space. Relax and enjoy the outdoor.......
3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1722
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. Rejuvenate from a day of Adventure or Business in our Lakefront property home.
ONLY 4 miles from LEGOLAND. Famous Orlando attractions (SeaWorld.......
Historic, sleeps 10+, 5 Bedroom, huge yard, lake, fishing, parks, events
Enjoy your stay in this large, peaceful, historic, fully renovated home. This home consists of 5 bedrooms, 3 bathrooms with modern kitchen, new AC, 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 also near the Lake Maude Park, and a short drive from many sports complexes........
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 Rating
4 Bedrooms
- Sleeps 12
Winter Haven Vacation Rental
Pet Friendly
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 Rating
6 Bedrooms
- Sleeps 13
Winter Haven Vacation Rental
Pet Friendly
Private Spacious 1BR Near LEGOLAND 2 Miles
WELCOME to our Wakulla Vacation Home (2), duplex property. We are a family own business & genuinely hope to tailor our properties to meet our Guest needs. We adhere to a 3 Core Property Standards that we expect; so, you'll always arrive to a home that is Safe, Clean and Guest Ready! This property is centrally located, 2 mi to dtwn Winter Haven and the Hospital & 2 mi to LEGOLAND & Peppa Pig. One of the best features of this property is a very private screened in porch with large fenced in yard........
Lake House to be leased with Main house: 2042348
23 Miles from Disney world, 35 Miles from Universal Studios. 5 miles 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 Main (Prop ID: 2042348) which has 3 Bed,.......
1 Bedrooms
- Sleeps 4
Winter Haven Vacation Rental
Waterfront Vacation Rental on Lake Mirror!
Situated directly on Lake Mirror, this charming Winter Haven vacation rental is perfect for snowbirds looking to embrace lake life and experience endless water sport recreation! Whether you spend your days fishing off the dock, exploring the lake, or watching local wildlife, you’ll love having this 2-bedroom, 2-bath abode as your home away from home. When not enjoying the outdoors, relax in the living room and admire the beautiful lakefront views or prepare dinner in the well-equipped kitchen........
Minutes to Legoland. Heated Pool and Private Hot Tub. Relaxation Awaits!
Relax in the pool and hot tub after enjoying theme parks such as Busch Gardens, Disney world, and Universal Studios! LegoLand is 1 mile away! Lego bedroom for kids. Centrally Located in the middle of Florida allows beach trips to both east & west coast. air conditioned garage has been turned into a game room pool table, air hockey and a actual miss pac-man machine with 14 different games installed inside. Also a Magnetic Dart board. Private boat & RV parking with RV outlet thru gate in backyard........
10.0 Star Rating
4 Bedrooms
- Sleeps 8
Winter Haven Vacation Rental
Pet Friendly
Spectacular Waterfront Home in Winter Haven
HIGHLIGHTS
+Custom built in 2006
+Chef’s kitchen with Viking Professional appliances
+Waterfront on 3 sides of the property!
+2 docks with boat cleats - bring your boat!
+Beautifully manicured grounds - all new lakeside landscaping
+Screen enclosed Florida Pool with hot tub
+Additional waterfront above ground hot tub
+West facing for fabulous sunsets
+Covered parking for 2 vehicles
+Upstairs and downstairs screened porches
+TVs in every room
CONVENIENCE.......
10.0 Star Rating
4 Bedrooms
- Sleeps 10
Winter Haven Vacation Rental
Pet Friendly
Cozy Lakefront Home w/ Pool -7 mins from Legoland
Discover family bliss at our 3-bedroom lakeside retreat in Winter Haven. Dive into the private pool, fire up the grill for al fresco feasts, and unwind in the Tulum-inspired luxury of your cozy abode. With a wealth of family-friendly activities nearby, from Legoland to lakeside strolls, this safe and quiet neighborhood is your gateway to cherished quality time. Create unforgettable memories in this tranquil haven. Book your stay today!.......
Private King Suite with W/D near LEGOLAND & Winter Haven Hospital
Centrally located Modern/Contemporary Spacious Private King Suite that is close to Winter Haven (WH) downtown (2 miles); WH Hospital (2 miles) & LEGOLAND (6 miles). It is perfect for couples+1 kid, solo adventure, or business travelers. This Spacious Private King Suite has a private bathroom (walk-in shower); memory foam King bed; Loveseat Sofa Bed (small convertible futon, folds down for a child); 55" Smart TV; covered parking; W&D, & Kitchenette. Easy check-in, private entrance w/keyless lock........
8.4 Star Rating
1 Bedrooms
- Sleeps 3
Winter Haven Vacation Rental
Pet Friendly
Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!
This lakeside cottage has a peaceful view of Eagle Lake. Close to Legoland resort and an easy drive to many central Florida destinations including Disney World parks, other Orlando destinations, Bok Singing Tower, Tampa beaches, etc. Local community events include free waterski shows and great restaurants. Amenities include high speed internet, flat screen TVs, family dining table and washer/dryer. Smart lock access allows arriving on your own schedule. Rent kayaks with local vendors. Perf.......