Vacation Rentals & Homes in Winter Haven Florida

Winter Haven Private vacation home

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 .......read more

4 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Winter Haven Apartment

This property is a beautifully updated 2/1 home. Property comes equipped with a full kitchen, living room, smart TV, central AC, high speed internet, gorgeous front and back porch, spacious shared back yard area, washer/dryer unit, and plenty parking. Property is located 4 minutes to downtown Winter Haven and 12 minutes to Legoland. Property is pe.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 5

Vacation Home

Winter Haven Private vacation home 4.8

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 sleepe.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 5

Vacation Home

Winter Haven Private vacation home

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/barefo.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 10

Vacation Home

Winter Haven Apartment

This property is a beautifully updated 2/1 home. Property comes equipped with a full kitchen, living room, smart TV, central AC, high speed internet, gorgeous front and back porch, spacious shared back yard area, washer/dryer unit, and plenty parking. Property is located 4 minutes to downtown Winter Haven and 12 minutes to Legoland. Property is pe.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 5

Vacation Home

Winter Haven Private vacation home 4.0

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 eight with one king bed, two queen beds, and one twin. The kitchen is fully stocked with pots, pans, dishes, and si.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 7

Vacation Home

Winter Haven Private vacation home 4.7

Located in Winter Haven, this handsomely furnished, all-inclusive 2 bedroom/2.5 bathroom townhouse is the ideal home-away-from-home when vacationing or working in Winter Haven or Central Florida. The townhouse, in beautiful downtown, is steps away from the city library, parks, coffee shop, countless restaurants and shops, and minutes away (by car) .......read more

2 Bedroom(s)
3 Bath(s) Sleeps 6

Vacation Home

Winter Haven Private vacation home 5.0

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.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Winter Haven Private vacation home 5.0

The Luxury Lakehouse

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

VACASA GUESTWORKS

This rental is operated and managed locally by an independent host.

Prior to your arrival, you will receive local host contact information, who .......read more

3 Bedroom(s)
3 Bath(s) Sleeps 7

Vacation Home

Winter Haven Private vacation home 4.8

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.......read more

3 Bedroom(s)
5 Bath(s) Sleeps 6

Vacation Home

Winter Haven Private vacation home

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 H.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Winter Haven Private vacation home

This three bedroom, two bath waterfront home on Lake Howard Drive has been fully remodeled on the inside with modern finishes and features. The interior boasts an open floor plan with hardwood floors, new appliances, and custom cabinetry in the kitchen. The living room features large windows with stunning views of the lake. All three bedrooms have .......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Winter Haven Private vacation home 4.5

Bring your family & friends and enjoy this amazing & relaxing lakefront view property with room for everyone to come together. Whether it's a family gathering, or to simply escape from the fast pace of everyday life, this is the place for you! This property has a peaceful sitting area with an incredible lakefront view and an amazing backyard. Appr.......read more

7 Bedroom(s)
5 Bath(s) Sleeps 21

Vacation Home

Winter Haven Private vacation home 5.0

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 are.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 10

Vacation Home

Winter Haven Private vacation home 4.7

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.......read more

6 Bedroom(s)
4 Bath(s) Sleeps 13

Vacation Home

WINTER HAVEN Private vacation home 4.9

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.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 12

Vacation Home

Winter Haven Private vacation home 5.0

CHECKOUT A FULL VIDEO OF THE PROPERTY:

https://youtu.be/K6zlvwkvq-o

★ SPACIOUS 5-STAR LUXURY WINTER HAVEN HOME ★

You will be awe-struck by modern architecture of this newly-remodeled 6 bedroom, 3 bath Florida vacation rental home! It is centrally located between the Orlando & Tampa areas for easy access to all of the entert.......read more

6 Bedroom(s)
3 Bath(s) Sleeps 12

Vacation Home

Winter Haven Private vacation home 5.0

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 .......read more

3 Bedroom(s)
2 Bath(s) Sleeps 7

Vacation Home

Winter Haven Private vacation home 4.9

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 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Winter Haven Private vacation home 4.5

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.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 5

Vacation Home

Winter Haven Private vacation home

Peace & Love Sanitized Private Room with private door entrance and bathroom. Wi-Fi, parking space for a Single person. Very quiet place recommended for nurses, students, teachers etc. Decorated with positive phrases so that you have an excellent physical, mental, emotional and spiritual rest. Located in the heart of Winter Haven, the room is safe, .......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2

Vacation Home

Winter Haven Private vacation home

This room is located 5 minutes from Winter Haven Hospital and is only designed to accommodate women, especially nurses and those who belong to the health sector. In this private room and shared bathroom you can enjoy the simplicity of this accommodation that has a spiritual touch, it is very clean, safe, quiet, comfortable, comfortable and with a v.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2

Vacation Home

Winter Haven Condo

We invite you to Stay and Play at our Updated 2 Bedroom Condo with an all around Lake View located in the Prestigious Gated Community of Winterset. You'll find yourself perfectly placed for a great Florida vacation.

Less than 90 Minutes drive from the Gulf and Atlantic coasts. It is a peaceful, gated community which is maintained to a high s.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Winter Haven Private vacation home

Bring the wwireless network
kitchen for cooking
air conditioner
television
washing machine
supporting facilities
free parking spacehole family into this fully remodeled pet friendly home with lots of room to entertain........read more

5 Bedroom(s)
2 Bath(s) Sleeps 16

Vacation Home

Winter Haven Private vacation home 5.0

Have fun with the family at this cozy home near Lake Shipp! 1.5 miles to Downtown, 5 miles to Legoland, 32 miles to Disney World. Our 3 bedroom, 4 beds, sleep 6 people. This home is designed with modern amenities to ensure a comfortable stay. Guests are greeted by a tastefully decorated interior that exudes comfort and warmth. Fully equipped kitche.......read more

3 Bedroom(s)
1 Bath(s) Sleeps 6

Vacation Home

Winter Haven Private vacation home 5.0

Come stay at Chanti's Place for your next stay. Experience a secret hideaway in this stylish, boho-modern designed home. This beautiful 4 bedroom, 2 bathroom home of Pinnacle Point is located in Winter Haven, Florida, the water ski capital of the world.

Activities and attractions within 15 minutes:
Marshall Hampton Reserve, Theatre Winter.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 10

Vacation Home

Winter Haven Private vacation home 4.7

The Lego House, where everything is awesome, thousands of Lego pieces for you to play, it is the AWESOMEST house, with Lego board games, a pool with giant Lego inspired blocks (not heated), Lego decorations, Lego themed bathrooms, a Lego themed kitchen, Lego everything, even a Lego Waffle Maker, also a classic arcade with 1,000’s of games, Smart .......read more

4 Bedroom(s)
2 Bath(s) Sleeps 10

Vacation Home

Winter Haven Private vacation home 5.0

Welcome to Lavish Dreams!
This New Modern Construction is furnished with comfortable, King Bed, full kitchen equipped, and a spacious living area with a 75-inch TV that is perfect for relaxation and entertainment.

You are only:

10 mins to Legoland
10 mins to Advent Health
20 mins to Chains of Lakes
11 mins to Eagle Ridge.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Winter Haven Private vacation home

Forget your worries in this spacious and serene space. This home is in a nice peaceful neighborhood near winter haven hospital.
Kitchen
Wifi
Free parking on premises
TV
Washer
Air conditioning
Security cameras on property.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Winter Haven Apartment 4.9

Guest Suite with completely separate entrance and full bath in safe, quiet neighborhood in the Cypress Gardens area of WH. 3 miles from State Farm Ops Center and 2 miles from Legoland. Although attached to main house, this hotel-like suite is totally separate from it and includes queen bed, fridge, microwave, coffee/tea maker, and desk with MFC pri.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 3

Vacation Home

Winter Haven Private vacation home 4.8

Great neighborhood! Peaceful, safe, friendly.

Close to Legoland! 5 minute drive (1 mile).

Relax and enjoy your time in Florida. The back yard has views of horse pastures and palm trees. The inside has all the amenities. We want you to keep coming back!

This 2 bed 1.5 bath home is perfect for a family visiting Legoland. There a.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

WINTER HAVEN Private vacation home

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,.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 1

Vacation Home

Winter Haven Private vacation home 4.8

Enjoy a relaxing escape to Winter Haven when you book this charming vacation rental home, complete with 2 bedrooms, 1.5 bathrooms, an office space for remote work, and much more! Fix up a meal on the charcoal grill or head out and try amazing local restaurants, all just a short drive away. For family fun, visit LEGOLAND, take a day trip to Walt Dis.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 7

Vacation Home

Winter Haven Private vacation home 5.0

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.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 6

Vacation Home

Winter Haven Private vacation home 4.5

About this space
Welcome to Lakeside Landing!

Get away from the hustle of the city to a tranquil getaway in Winter Haven. Tour the many lakes the city has to offer or even stop by Legoland (15 mins away) to spend a day with the kids.

This modern home is furnished with clean white linens and calming neutral tones to make our custome.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Winter Haven Private vacation home 4.8

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 worl.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home