Vacation Rentals with Private Pool in Cypresswood Golf and Country Club, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Lakeland - Winter Haven

  6.  Cypresswood Golf and Country Club

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89 Best Vacation Rentals with Private Pool in Cypresswood Golf and Country Club (Starting from $218)

Modern Haines City Home with Pool and Lanai!
Modern Haines City Home with Pool and Lanai!
House
Haines City, FL, USA
9.7k from Cypresswood Golf and Country Club center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

4 Bedrooms8 Guests
8.5

Very Good

4 reviews

$319
Average price / night
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Luxury Lakefront | Heated Salt Pool, Dock & Kayaks | Home Theatre & EV Charger | Near Theme Parks
Luxury Lakefront | Heated Salt Pool, Dock & Kayaks | Home Theatre & EV Charger | Near Theme Parks
House
Winter Haven, FL, 33881, United States
2.4k from Cypresswood Golf and Country Club center

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

6 Bedrooms13 Guests
9.6

Exceptional

18 reviews

$692
Average price / night
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Heated Pool Backyard Fun | Kayaks | Boat Dock | Lake Access | Theater Room | EV Charger Theme Parks
Heated Pool Backyard Fun | Kayaks | Boat Dock | Lake Access | Theater Room | EV Charger Theme Parks
House
Winter Haven, FL, 33881, United States
2.4k from Cypresswood Golf and Country Club center

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

3 Bedrooms6 Guests
9.8

Exceptional

16 reviews

$337
Average price / night
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Heated Pool and Hot tub-near Legoland, Disney, Theme parks
Heated Pool and Hot tub-near Legoland, Disney, Theme parks
House
Winter Haven, FL, 33884, United States
4.0k from Cypresswood Golf and Country Club center

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

4 Bedrooms8 Guests
9.8

Exceptional

47 reviews

$431
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
4.2k from Cypresswood Golf and Country Club 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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Lakefront Lego Land Estate
Lakefront Lego Land Estate
House
Winter Haven, FL, 33884, United States
4.6k from Cypresswood Golf and Country Club 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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Beautiful home located in a gated community only 20 miles from LegoLand!
Beautiful home located in a gated community only 20 miles from LegoLand!
House
Winter Haven, FL, 33881, United States
4.7k from Cypresswood Golf and Country Club center

AC, Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

17 reviews

$432
Average price / night
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Luxury Lakehouse on Lake Ruby - Dock - Game Room - Near Legoland
Luxury Lakehouse on Lake Ruby - Dock - Game Room - Near Legoland
House
Winter Haven, FL, 33884, United States
4.8k from Cypresswood Golf and Country Club center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, No Smoking

3 Bedrooms8 Guests
New to Booking
$495
Average price / night
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Beautiful Lake Front cottage w/ heated pool & Hot Tub, 23 miles from Disney
Beautiful Lake Front cottage w/ heated pool & Hot Tub, 23 miles from Disney
House
Main House Winter Haven, FL, 33881, United States
4.9k from Cypresswood Golf and Country Club center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
9.8

Exceptional

29 reviews

$308
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
5.4k from Cypresswood Golf and Country Club 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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Lake Hamilton Oasis - Pool • Dock • Sunrise Views
Lake Hamilton Oasis - Pool • Dock • Sunrise Views
House
Winter Haven, FL, 33881, United States
5.4k from Cypresswood Golf and Country Club center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
New to Booking
$321
Average price / night
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Heated Pool, Arcade with PS5, 5min from Legoland-Stylish LakeHome
Heated Pool, Arcade with PS5, 5min from Legoland-Stylish LakeHome
House
Winter Haven, FL, 33884, United States
5.4k from Cypresswood Golf and Country Club center

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

3 Bedrooms7 Guests
10.0

Exceptional

11 reviews

$387
Average price / night
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An Amazing Mid-Century Modern Experience
An Amazing Mid-Century Modern Experience
House
Winter Haven, FL, 33881, United States
5.6k from Cypresswood Golf and Country Club center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
New to Booking
$512
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
5.7k from Cypresswood Golf and Country Club 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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Ultimate Family Getaway: 4BR Home with Pool & Games
Ultimate Family Getaway: 4BR Home with Pool & Games
House
Winter Haven, FL, 33881, United States
5.8k from Cypresswood Golf and Country Club center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

5 Bedrooms10 Guests
New to Booking
$408
Average price / night
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Spectacular Waterfront Home in Winter Haven
Spectacular Waterfront Home in Winter Haven
House
Winter Haven, FL, 33884, United States
5.8k from Cypresswood Golf and Country Club center

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

4 Bedrooms10 Guests
10.0

Exceptional

26 reviews

$923
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, 33884, United States
5.8k from Cypresswood Golf and Country Club center

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

3 Bedrooms8 Guests
8.4

Very Good

9 reviews

$243
Average price / night
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Huge Luxury Lake House on the Chain of Lakes near Legoland!
Huge Luxury Lake House on the Chain of Lakes near Legoland!
House
Winter Haven, FL, 33884, United States
6.0k from Cypresswood Golf and Country Club center

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

5 Bedrooms15 Guests
9.8

Exceptional

113 reviews

$548
Average price / night
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Lake View, Game Room, 10 minutes to Legoland - Perfect for Large Families!
Lake View, Game Room, 10 minutes to Legoland - Perfect for Large Families!
House
Winter Haven, FL, 33880, United States
6.1k from Cypresswood Golf and Country Club center

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

4 Bedrooms11 Guests
10.0

Exceptional

12 reviews

$514
Average price / night
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Legoland Pool House with Suite  4 bedroom 2 bathroom
Legoland Pool House with Suite 4 bedroom 2 bathroom
House
Winter Haven, FL, 33884, United States
6.2k from Cypresswood Golf and Country Club center

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

4 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$289
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!
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!
House
Winter Haven, FL, 33880, United States
6.4k from Cypresswood Golf and Country Club center

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

3 Bedrooms8 Guests
6.0

Review score

1 reviews

$318
Average price / night
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Newly remodeled Vacation Home with Saltwater Pool
Newly remodeled Vacation Home with Saltwater Pool
House
Winter Haven, FL, 33884, United States
6.4k from Cypresswood Golf and Country Club center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$234
Average price / night
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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
6.5k from Cypresswood Golf and Country Club center

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

4 Bedrooms10 Guests
10.0

Exceptional

13 reviews

$638
Average price / night
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Family Friendly Lake House W/ Pool Near Legoland
Family Friendly Lake House W/ Pool Near Legoland
House
Winter Haven, FL, 33880, United States
6.5k from Cypresswood Golf and Country Club center

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

5 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$9219
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
6.8k from Cypresswood Golf and Country Club 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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Private pool lake house with game room—just 4 minutes from LEGOLAND
Private pool lake house with game room—just 4 minutes from LEGOLAND
House
WINTER HAVEN, FL, 33884, United States
7.1k from Cypresswood Golf and Country Club center

AC, Arcade, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
10.0

Exceptional

74 reviews

$391
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
7.2k from Cypresswood Golf and Country Club 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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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 with Private Pool in Cypresswood Golf and Country Club.

Where to stay in Cypresswood Golf and Country Club? Best neighborhoods & areas

Cypresswood Golf and Country Club Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 89 verified vacation rentals with a private pool in Cypresswood Golf and Country Club. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Cypresswood Golf and Country Club vary depending on the property size, location, and travel season. Rates typically start from around $218 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Cypresswood Golf and Country Club also welcome pets. Currently, 8 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Cypresswood Golf and Country Club often include additional features such as Private Pool, Pool, and Bedding/Linens. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Cypresswood Golf and Country Club include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.