Winter Haven Vacation Rentals from ￥8,624: Search Short-Term Rentals

Q: What's the top vacation rental that Winter Haven has to offer?

Formosa Valley Resort by UNE Homes : This vacation home rental outside Winter Haven is equipped with an outdoor pool, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

A LEGO-themed welcome sign with 'LEGO FLORIDA' and 'WELCOME' in large letters, surrounded by greenery.

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Our top choices for Winter Haven vacation rentals

A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.

1. The Russell Lake House

Winter Haven

Jake D.

￥30,921 total

includes taxes & fees

Nov 16 - Nov 17

A building with a red door, numbered 132C, and a small porch area with a metal stool and a green bucket with a wooden stick.

2. Tiny Paradise

Winter Haven

Paula

￥18,808 total

includes taxes & fees

Nov 29 - Nov 30

A swimming pool with a fence, lounge chairs, and a palm tree.

3. Lake Ida Beach Resort

Winter Haven

Heather

￥13,848 total

includes taxes & fees

Nov 16 - Nov 17

A kitchen with white cabinets, a dining table with chairs, and a ceiling fan.

4. Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

Winter Haven

John G.

￥44,535 total

includes taxes & fees

Nov 15 - Nov 16

A compact living space with a loft bed, a TV mounted on the wall displaying streaming services, a small bathroom, and a wooden floor.

5. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

winter have

Kyle P.

￥22,487 total

includes taxes & fees

Nov 29 - Nov 30

A kitchen with white cabinets, a black countertop, a window with blinds, and a light fixture.

6. Cozy 1-Bedroom Retreat Near Downtown & Legoland

Winter Haven

￥23,193 total

includes taxes & fees

Nov 16 - Nov 17

A living room with a large mural of marine life, a ceiling fan, a flat-screen TV, and a dining area in the background.

7. BlockHaven near Legoland & Disney

Winter Haven

Yuliett

￥38,816 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

8. Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Winter Haven

Debi K.

￥48,720 total

includes taxes & fees

Nov 17 - Nov 18

A spacious living room with a sofa, a recliner, and a glass coffee table. There is a kitchen area in the background with a microwave and refrigerator.

9. Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Winter Haven

Rachel B.

￥42,922 total

includes taxes & fees

Nov 17 - Nov 18

A wooden house with a porch, steps, and a fenced area with plants.

10. The Old Haven - An Enduring Piece of Nostalgia

Winter Haven

Ericka

￥47,833 total

includes taxes & fees

Nov 17 - Nov 18

11. 3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724

Winter Haven

Tim M.

￥43,122 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with a stainless steel refrigerator, white cabinetry, a double sink, and a painting of flowers on the wall.

12. New Haven 5 mi to Legoland & 0.5 mi to dwntwn

Winter Haven

￥41,716 total

includes taxes & fees

Nov 15 - Nov 16

A compact living space with a dining area, kitchen, and a seating area with a sofa and a rug.

13. Family-Friendly 2BR Near LEGOLAND with Parking

Winter Haven

Carolyn S.

￥30,473 total

includes taxes & fees

Nov 17 - Nov 18

A kitchen with a dining table, chairs, and a ceiling fan.

14. Cozy 3br 2ba Winter Haven Getaway Chain of Lakes

Winter Haven

Felix P.

￥43,002 total

includes taxes & fees

Nov 16 - Nov 17

A living room with a grey sectional sofa, a white round coffee table, a fluffy rug, and a decorative mirror on the wall.

15. Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

Winter Haven

Emilly D.

￥38,650 total

includes taxes & fees

Dec 1 - Dec 2

A living room with a brick fireplace, a sofa, a coffee table, and a dining area in the background.

16. Spacious 4-bedroom house in pleasant Winter Haven with AC

Winter Haven

Monica

￥59,872 total

includes taxes & fees

Nov 16 - Nov 17

An outdoor hot tub area with a pool, surrounded by chairs and a table.

17. Legoland Splash Escape with pool and hot tub!

Winter Haven

Michelle

￥51,166 total

includes taxes & fees

Nov 17 - Nov 18

A bedroom with a large bed, a ceiling fan, a mirror, and a small bedside table with a lamp.

18. Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games

Winter Haven

Oscar G.

￥54,589 total

includes taxes & fees

Nov 23 - Nov 24

A modern living room with a marble floor, a ceiling fan, a flat-screen TV, a sofa, and a kitchen in the background.

19. View Private Suite near LEGOLAND & Hospital

Winter Haven

￥19,421 total

includes taxes & fees

Nov 16 - Nov 17

A compact hotel room with a bed, a sofa, a desk, a kitchenette, and a TV.

20. Private King Suite with W/D near LEGOLAND & Winter Haven Hospital

Winter Haven

Mike S.

￥26,959 total

includes taxes & fees

Nov 15 - Nov 16

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Find vacation rentals that suit your style

Top Winter Haven Hotel Reviews

A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

Staybridge Suites Winter Haven Auburndale by IHG

Winter Haven

10/10 Excellent

Grabiela

BlockHaven near Legoland & Disney

Winter Haven

10/10 Excellent

Yuliett

A hotel room with two beds, a desk, a microwave, a TV, and a painting on the wall.

Best Western Plus Winter Haven Inn & Suites

Winter Haven

10/10 Excellent

Ricardo

A hotel entrance with a glass canopy, a reception desk, and a seating area with plants.

Holiday Inn Express & Suites Lakeland South by IHG

Lakeland

10/10 Excellent

It’s in a great part of Lakeland, lots of restaurants and shops nearby. Easy access to I4 and other major roads. Hotel itself was very nice. Loved the high ceilings in the room we were in. Reasonably priced and the free breakfast was one of the best I’ve ever had at a hotel! Only downside to me was there were a few chairs in the room and when you had the pullout couch bed out it was crowded and not really any place to put the chair out of the way but other than that it was excellent!

Anonymous traveler

A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

Kompose Boutique Resort at Theme Parks

Kissimmee

10/10 Excellent

Patrik

A Holiday Inn hotel with a clear entrance, multiple flags, and a covered parking area.

Holiday Inn Winter Haven by IHG

Winter Haven

10/10 Excellent

Modupe D

A Hampton Inn hotel with a clear entrance, a covered waiting area, and a sign indicating a clearance of 13'6".

Hampton Inn Winter Haven

Winter Haven

10/10 Excellent

janet

An outdoor patio with a fire pit, wicker furniture, and a checkered wall.

SpringHill Suites by Marriott Lakeland

Downtown Lakeland

10/10 Excellent

mark

A modern hotel reception area with a wooden reception desk, a seating area with a table and chairs, and a large wall with geometric patterns.

Holiday Inn Express Lake Wales N-Winter Haven by IHG

Lake Wales

10/10 Excellent

Paula

A modern café with wooden tables and chairs, a counter with a coffee machine, and a refrigerator.

Home2 Suites by Hilton Orlando South Davenport

Davenport

10/10 Excellent

Yam

A spacious lobby with a grand chandelier, large windows offering a view of a pool, and a second-floor balcony with a railing.

The Berkley, Orlando

Kissimmee

10/10 Excellent

rick

A resort with multiple swimming pools, a large central pool, and a lake.

Embassy Suites By Hilton Orlando Sunset Walk

Kissimmee

10/10 Excellent

This property gave me international resort vibes in Florida. It really was an oasis. I had a two bedroom and our party was five, three were children. The entire property is clean. The staff from the front desk to the support staff were polite and professional. Great location, if you only want to drive a couple of minutes for access to restaurants, you're in a perfect location. It's also not too far out from the theme parks. TIP: There is a $40 daily resort fee that will be deducted from your...

Serene

An outdoor seating area with a fire feature, wicker chairs, and a stone fireplace.

TownePlace Suites by Marriott Plant City

Plant City

10/10 Excellent

Omar

A pool area with lounge chairs and umbrellas, surrounded by tropical plants.

ette hotel Orlando

Kissimmee

10/10 Excellent

I absolutely loved this place! It is so clean, charming, & beautifully decorated. The set-up and design of the rooms was so thought out and not a single detail was missed. The room had amazing linens, high-end bathrobes, toiletries and slippers. I was offered turn down service with fresh water every night and my room was always nice and clean when I returned at the end of the day. I love that's it's family owned - the owners did such a great job at making me feel at home. The restaurant has...

Michelle

Find out more about Winter Haven

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Frequently Asked Questions

Can I find a vacation rental in Winter Haven?

Yes, there are vacation rentals in Winter Haven close to LEGOLAND® Florida, or you can choose a more secluded option if you'd like a relaxing place to stay. Visitors to Winter Haven speak positively about the scenic lakeside and top-notch restaurants in this destination. Leave time to check out the gardens and entertainment venues during your visit.

What's the top vacation rental that Winter Haven has to offer?

Formosa Valley Resort by UNE Homes: This vacation home rental outside Winter Haven is equipped with an outdoor pool, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

How many vacation rentals are there in Winter Haven?

Choose from 53 Expedia vacation rentals in Winter Haven for a memorable vacation.

What can I see and do in Winter Haven?

Family-friendly attractions include LEGOLAND® Florida and Peppa Pig Theme Park Florida, whereas The Circle B Bar Reserve and Inman Park are a couple of great spots to enjoy the outdoors. Theatre Winter Haven and Chain of Lakes Park are other places to visit while you're in town.

What are vacation rentals like in Winter Haven?

Vacation rentals are private properties you can book for a few days or a quick weekend in Winter Haven. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.

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Winter Haven Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Haven vacation rentals

1. The Russell Lake House

2. Tiny Paradise

3. Lake Ida Beach Resort

4. Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

5. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

6. Cozy 1-Bedroom Retreat Near Downtown & Legoland

7. BlockHaven near Legoland & Disney

8. Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

9. Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

10. The Old Haven - An Enduring Piece of Nostalgia

11. 3BR/2BA Lake Mariam Home Near LEGOLAND with Kitchen & Laundry_1724

12. New Haven 5 mi to Legoland & 0.5 mi to dwntwn

13. Family-Friendly 2BR Near LEGOLAND with Parking

14. Cozy 3br 2ba Winter Haven Getaway Chain of Lakes

15. Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

16. Spacious 4-bedroom house in pleasant Winter Haven with AC

17. Legoland Splash Escape with pool and hot tub!

18. Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games

19. View Private Suite near LEGOLAND & Hospital

20. Private King Suite with W/D near LEGOLAND & Winter Haven Hospital

Find vacation rentals that suit your style

Top Winter Haven Hotel Reviews

Staybridge Suites Winter Haven Auburndale by IHG

10/10 Excellent

Find out more about Winter Haven

Frequently Asked Questions

Can I find a vacation rental in Winter Haven?

What's the top vacation rental that Winter Haven has to offer?

How many vacation rentals are there in Winter Haven?

What can I see and do in Winter Haven?

What are vacation rentals like in Winter Haven?

Explore a world of travel with Expedia