Vacation Rentals in Cypress Gardens, FL: Compare 10+ Sites & Save

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  3.  USA

  4.  Florida
  5.  Lakeland - Winter Haven

  6.  Cypress Gardens

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225 Best Vacation Rentals in Cypress Gardens (Starting from $52)

2Bed 1Bath CentralLocation 2 Mile LEGOLAND and Dining
2Bed 1Bath CentralLocation 2 Mile LEGOLAND and Dining
House
Cypress Gardens, FL, USA
0.6k from Cypress Gardens center

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

2 Bedrooms5 Guests
9.0

Fabulous

3 reviews

$117
Average price / night
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★2/1★Central★Location★☀2-Mile LEGOLAND&Dining☀
★2/1★Central★Location★☀2-Mile LEGOLAND&Dining☀
House
Winter Haven, FL, 33884, United States
0.1k from Cypress Gardens center

AC, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, TV

2 Bedrooms5 Guests
9.0

Fabulous

16 reviews

$143
Average price / night
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Stylish-N-Private 1BR Retreat 2 Miles to LegoLand
Stylish-N-Private 1BR Retreat 2 Miles to LegoLand
House
Winter Haven, FL, USA
0.6k from Cypress Gardens center

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

1 Bedroom4 Guests
8.7

Fabulous

12 reviews

$105
Average price / night
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Luxury 3BR Lake House on Quiet Private Lake, with Pool and Hot Tub
Luxury 3BR Lake House on Quiet Private Lake, with Pool and Hot Tub
House
Winter Haven, FL, 33884, United States
0.2k from Cypress Gardens center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
9.6

Exceptional

28 reviews

$280
Average price / night
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Private Entrance 1 Bd Guest Suite in Cypress Gardens near Legoland
Private Entrance 1 Bd Guest Suite in Cypress Gardens near Legoland
House
Cypress Gardens, Winter Haven, Florida, USA
0.7k from Cypress Gardens center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Places to stay

1 Bedroom5 Guests
9.6

Exceptional

30 reviews

$52
Average price / night
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Lakefront home with heated pool minutes from Legoland
Lakefront home with heated pool minutes from Legoland
House
Winter Haven, FL, 33884, United States
0.3k from Cypress Gardens center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

5 Bedrooms12 Guests
New to Booking
$656
Average price / night
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Modern 3 Bed 2 Bath Home 3 minutes from Legoland
Modern 3 Bed 2 Bath Home 3 minutes from Legoland
House
Winter Haven, FL, USA
0.9k from Cypress Gardens center

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

3 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$170
Average price / night
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Cozy Haven Apartment
Cozy Haven Apartment
Apartment
Winter Haven, FL, 33884, United States
0.4k from Cypress Gardens center

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

1 Bedroom2 Guests
10.0

Exceptional

15 reviews

$95
Average price / night
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Winter Haven Retreat with Private Pool!
Winter Haven Retreat with Private Pool!
House
Winter Haven, FL, USA
1.6k from Cypress Gardens 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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 3/ 2 kid friendly home, only minutes to Legoland.
3/ 2 kid friendly home, only minutes to Legoland.
House
Winter Haven, FL, 33884, United States
0.4k from Cypress Gardens center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

28 reviews

$198
Average price / night
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Cozy Lakefront Home w/Pool -7 mins from Legoland
Cozy Lakefront Home w/Pool -7 mins from Legoland
House
Winter Haven, FL, USA
1.7k from Cypress Gardens center

View, Parking, Ocean View, Barbecue/Outdoor Cooking, Internet, Oceanfront, Security/Safety

3 Bedrooms8 Guests
7.8

Good

8 reviews

$194
Average price / night
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Private Entrance 1 Bd 1.5 Bath Guest Suite in Cypress Gardens near Legoland
Private Entrance 1 Bd 1.5 Bath Guest Suite in Cypress Gardens near Legoland
Apartment
Winter Haven, FL, 33884, United States
0.4k from Cypress Gardens center

AC, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, Patio, TV

1 Bedroom5 Guests
10.0

Exceptional

23 reviews

$79
Average price / night
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Bright Cypress Gardens Home Near Legoland!
Bright Cypress Gardens Home Near Legoland!
House
Cypress Gardens, FL, USA
1.7k from Cypress Gardens center

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

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$143
Average price / night
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Waterfront-Heated SaltWtr Pool-Putting Green-Beach-FirePit-Dock-Sunsets-Legoland
Waterfront-Heated SaltWtr Pool-Putting Green-Beach-FirePit-Dock-Sunsets-Legoland
House
Winter Haven, FL, 33884, United States
0.5k from Cypress Gardens center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

5 Bedrooms16 Guests
9.6

Exceptional

5 reviews

$848
Average price / night
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Stylish Lake home with HUGE POOL, Arcade with PS5,and Theater Just 5 min from Legoland
Stylish Lake home with HUGE POOL, Arcade with PS5,and Theater Just 5 min from Legoland
House
Winter Haven, FL, USA
1.7k from Cypress Gardens center

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

3 Bedrooms6 Guests
8.6

Fabulous

10 reviews

$269
Average price / night
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5 BR home with large patio, pool & outdoor family fun - 7 mins to LEGOLAND!
5 BR home with large patio, pool & outdoor family fun - 7 mins to LEGOLAND!
House
Winter Haven, FL, 33884, United States
0.5k from Cypress Gardens center

AC, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Patio

5 Bedrooms12 Guests
9.6

Exceptional

4 reviews

$392
Average price / night
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3Bed 2Bath Spacious-LakeHomeAceLoc4milesLEGOLAND
3Bed 2Bath Spacious-LakeHomeAceLoc4milesLEGOLAND
House
Cypress Gardens, FL, USA
2.2k from Cypress Gardens center

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

3 Bedrooms7 Guests
7.7

Good

4 reviews

$139
Average price / night
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Spacious 4-bedroom house in pleasant Winter Haven with AC
Spacious 4-bedroom house in pleasant Winter Haven with AC
House
Winter Haven, FL, 33884, United States
0.5k from Cypress Gardens center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$464
Average price / night
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1Bed 1Bath Container Home Centrally Located
1Bed 1Bath Container Home Centrally Located
Ski Chalet
Cypress Gardens, FL, USA
2.2k from Cypress Gardens center

Cheap, Accommodations, Parking, Cabins, Cottages, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom3 Guests
8.7

Fabulous

13 reviews

$91
Average price / night
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Family-Friendly Pool Home Just Minutes from Legoland — Sleeps 6+!
Family-Friendly Pool Home Just Minutes from Legoland — Sleeps 6+!
House
Winter Haven, FL, 33884, United States
0.6k from Cypress Gardens center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$323
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
2.4k from Cypress Gardens 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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Lakefront Lego Land Estate
Lakefront Lego Land Estate
House
Winter Haven, FL, 33884, United States
0.7k from Cypress Gardens center

AC, Arcade, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking

5 Bedrooms8 Guests
9.8

Exceptional

29 reviews

$438
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
2.4k from Cypress Gardens 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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Private/Spacious 1BR Central Near LegoLand 2 Miles
Private/Spacious 1BR Central Near LegoLand 2 Miles
House
Winter Haven, FL, 33884, United States
0.8k from Cypress Gardens center

AC, Dryer, Internet, Laundry, Living Area, No Smoking, Outdoor Space, Washer

1 Bedroom5 Guests
9.2

Superb

12 reviews

$172
Average price / night
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Beautiful Private Newer and Gated 55+ Community.
Beautiful Private Newer and Gated 55+ Community.
Villa
Winter Haven, FL, 33884, United States
1.2k from Cypress Gardens center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms3 Guests
New to Booking
$208
Average price / night
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Romantic & Spicy Getaway w/ Mermaid Pool & Hot Tub. Adults only!
Romantic & Spicy Getaway w/ Mermaid Pool & Hot Tub. Adults only!
House
Winter Haven, FL, 33884, United States
1.6k from Cypress Gardens center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.6

Exceptional

4 reviews

$485
Average price / night
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Winter Haven Retreat w/ Private Pool!
Winter Haven Retreat w/ Private Pool!
House
Winter Haven, FL, 33884-1938, United States
1.6k from Cypress Gardens center

AC, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.2

Superb

17 reviews

$314
Average price / night
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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 Cypress Gardens.

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Frequently Asked Questions

You can explore 225 verified vacation rentals in Cypress Gardens. 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 Cypress Gardens vary depending on the season, property size, and location. Rates typically start from around $52 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 Cypress Gardens 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 Cypress Gardens welcome pets. Currently, 35 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 Cypress Gardens often include amenities such as Fireplace/Heating, Balcony/Terrace, and Child Friendly. 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.