Vacation Rentals in Theatre Winter Haven, FL: Compare 10+ Sites & Save

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229 Best Vacation Rentals in Theatre Winter Haven (Starting from $103)

Waterfront Winter Haven Home with Dock and Hot Tub!
Waterfront Winter Haven Home with Dock and Hot Tub!
House
Winter Haven, FL, USA
1.1k from Theatre Winter Haven center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

4 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$315
Average price / night
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Charming 2-bedroom country house with AC, WiFi in Winter Haven
Charming 2-bedroom country house with AC, WiFi in Winter Haven
House
Winter Haven, FL, 33880, United States
0.8k from Theatre Winter Haven center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
7.0

Good

9 reviews

$125
Average price / night
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Unique cozy studio
Unique cozy studio
Apartment
Winter Haven, FL, USA
1.5k from Theatre Winter Haven center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom2 Guests
9.8

Exceptional

5 reviews

$106
Average price / night
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Costa 5BD Lego Pool Home - Your Own Private Resort
Costa 5BD Lego Pool Home - Your Own Private Resort
House
Winter Haven, FL, 33880, United States
0.9k from Theatre Winter Haven center

AC, Dryer, Heater, Internet, Laundry, Living Area, No Smoking, Washer

5 Bedrooms12 Guests
New to Booking
$390
Average price / night
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Cozy Bungalow
Cozy Bungalow
House
Winter Haven, FL, USA
1.5k from Theatre Winter Haven center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family, Bungalows

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$183
Average price / night
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Waterfront Winter Haven Home with Dock & Hot Tub!
Waterfront Winter Haven Home with Dock & Hot Tub!
House
Winter Haven, FL, 33880, United States
1.1k from Theatre Winter Haven center

AC, Arcade, Bar, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

4 Bedrooms12 Guests
10.0

Exceptional

68 reviews

$456
Average price / night
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Getaway Clubhouse
Getaway Clubhouse
House
Winter Haven, FL, USA
1.5k from Theatre Winter Haven center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$218
Average price / night
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Cute & Cozy 1 bedroom guesthouse located in Winter Haven FL
Cute & Cozy 1 bedroom guesthouse located in Winter Haven FL
House
Winter Haven, FL, 33880, United States
1.2k from Theatre Winter Haven center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom2 Guests
10.0

Exceptional

19 reviews

$103
Average price / night
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4 Mi to Legoland Poolside Paradise!
4 Mi to Legoland Poolside Paradise!
House
Winter Haven, FL, USA
1.5k from Theatre Winter Haven center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms5 Guests
New to Booking
$302
Average price / night
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Tiny Paradise
Tiny Paradise
Apartment
Winter Haven, FL, 33880, United States
1.5k from Theatre Winter Haven center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio

1 Bedroom2 Guests
9.4

Superb

11 reviews

$124
Average price / night
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Sweet Cottage
Sweet Cottage
House
Winter Haven, FL, USA
1.6k from Theatre Winter Haven center

Accommodations, Country houses, Cottages, Lodgings, Places to stay

2 Bedrooms8 Guests
New to Booking
$196
Average price / night
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The Unique cozy studio
The Unique cozy studio
Apartment
Winter Haven, FL, 33880, United States
1.5k from Theatre Winter Haven center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom2 Guests
9.0

Fabulous

2 reviews

$116
Average price / night
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Winter Haven Home with Pool Near Legoland!
Winter Haven Home with Pool Near Legoland!
House
Winter Haven, FL, USA
1.8k from Theatre Winter Haven center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

3 Bedrooms8 Guests
9.6

Exceptional

11 reviews

$231
Average price / night
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Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
House
Winter Haven, FL, 33880, United States
1.5k from Theatre Winter Haven center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$286
Average price / night
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The Old Haven - An Enduring Piece of Nostalgia
The Old Haven - An Enduring Piece of Nostalgia
House
Winter Haven, FL, USA
1.8k from Theatre Winter Haven center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

4 Bedrooms9 Guests
9.0

Fabulous

1 reviews

$208
Average price / night
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Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
House
Winter Haven, FL, 33880, United States
1.5k from Theatre Winter Haven center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
9.8

Exceptional

12 reviews

$306
Average price / night
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Pool 9min Legoland Disney Universal 40 Min
Pool 9min Legoland Disney Universal 40 Min
House
Cypress Gardens, FL, USA
1.8k from Theatre Winter Haven center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Accessible hotels

3 Bedrooms8 Guests
New to Booking
$288
Average price / night
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Work, Play or Recharge:3BR Pool Home near Legoland
Work, Play or Recharge:3BR Pool Home near Legoland
House
Winter Haven, FL, 33880, United States
1.5k from Theatre Winter Haven center

AC, Barbecue, Dryer, Fitness Equipment, Internet, Microwave, No Smoking, Pool, Toys

3 Bedrooms5 Guests
New to Booking
$218
Average price / night
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Large 3Bedrooms 1 Bath Near DownTown Dining
Large 3Bedrooms 1 Bath Near DownTown Dining
House
Winter Haven, FL, USA
1.9k from Theatre Winter Haven center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms8 Guests
8.5

Very Good

8 reviews

$160
Average price / night
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Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Cottage
Winter Haven, FL, 33880, United States
1.6k from Theatre Winter Haven center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

2 Bedrooms8 Guests
8.8

Fabulous

5 reviews

$273
Average price / night
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Winter Haven Retreat with Private Pool!
Winter Haven Retreat with Private Pool!
House
Winter Haven, FL, USA
2.6k from Theatre Winter Haven center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
7.8

Good

6 reviews

$236
Average price / night
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Lake Shipp House with pool and dock on the water
Lake Shipp House with pool and dock on the water
House
Winter Haven, FL, 33880, United States
1.6k from Theatre Winter Haven center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

26 reviews

$247
Average price / night
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Lakeside Lofts at Lake Martha
Lakeside Lofts at Lake Martha
Villa
Winter Haven, FL, USA
2.6k from Theatre Winter Haven center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Self-catering

4 Bedrooms6 Guests
9.3

Superb

16 reviews

$182
Average price / night
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Little Haven — Winter Haven's top-rated 3BR/2BA with private pool & modern amenities. Sleeps 8. Minutes from LEGOLAND Florida, Walt Disney World, Universal Studios & SeaWorld. Perfect for family vacations, reunions & Orlando getaways. Instant book!
6.0

Review score

1 reviews

$318
Average price / night
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Smart Home 2-bedroom house in marvelous Winter Haven with AC, Netflix, Alexa.
Smart Home 2-bedroom house in marvelous Winter Haven with AC, Netflix, Alexa.
House
Winter Haven, FL, 33880, United States
1.8k from Theatre Winter Haven center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms5 Guests
New to Booking
$153
Average price / night
Check Availability
Lakeside Adventure Retreat w/ Heated Pool, Fishing Dock, Game Room & Optional 1 hr Boat Cruise*
Lakeside Adventure Retreat w/ Heated Pool, Fishing Dock, Game Room & Optional 1 hr Boat Cruise*
House
Winter Haven, FL, 33880, United States
1.9k from Theatre Winter Haven center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

13 reviews

$638
Average price / night
Check Availability
Charming 3-bedroom  2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
House
Winter Haven, FL, 33880, United States
2.0k from Theatre Winter Haven center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$212
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Theatre Winter Haven.

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Theatre Winter Haven Vacation Rentals on the Map

Frequently Asked Questions

You can explore 229 verified vacation rentals in Theatre Winter Haven. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Theatre Winter Haven vary depending on the season, property size, and location. Rates typically start from around $103 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Theatre Winter Haven include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Theatre Winter Haven welcome pets. Currently, 38 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Theatre Winter Haven often include amenities such as Fireplace/Heating, Guest Services, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.