Vacation Rentals in Winter Pines Golf Course, FL: Compare 10+ Sites & Save

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  3.  USA

  4.  Florida
  5.  Lakeland - Winter Haven

  6.  Winter Pines Golf Course

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309 Best Vacation Rentals in Winter Pines Golf Course (Starting from $52)

John Shirleys Retreat
John Shirleys Retreat
House
Winter Haven, FL, USA
2.9k from Winter Pines Golf Course center

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

3 Bedrooms6 Guests
8.2

Very Good

5 reviews

$176
Average price / night
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Florida Chill\nSunshine by Day, Fire Pit Nights — 3BR with AC in Winter Haven
Florida Chill\nSunshine by Day, Fire Pit Nights — 3BR with AC in Winter Haven
House
Winter Haven, FL, 33884, United States
1.6k from Winter Pines Golf Course center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$216
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
Winter Pines Golf Course, Winter Haven, Florida, USA
3.8k from Winter Pines Golf Course 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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Elita Inn
Elita Inn
Apartment
28550 U.S. 27, Dundee, FL, 33838, United States
1.7k from Winter Pines Golf Course center

AC, Free Parking, Frontdesk 24 Hour, Internet, Laundry, Microwave, No Smoking

1 Bedroom3 Guests
7.6

Good

28 reviews

$89
Average price / night
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2Bed 1Bath CentralLocation 2 Mile LEGOLAND and Dining
2Bed 1Bath CentralLocation 2 Mile LEGOLAND and Dining
House
Cypress Gardens, FL, USA
4.0k from Winter Pines Golf Course 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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New Modern Studio/Guest House in serene Dundee, Great Location, Smoke-Free
New Modern Studio/Guest House in serene Dundee, Great Location, Smoke-Free
Apartment
Dundee, FL, 33838, United States
2.0k from Winter Pines Golf Course center

AC, Heater, Internet, No Smoking

1 Bedroom4 Guests
New to Booking
$67
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
4.0k from Winter Pines Golf Course 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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Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven
Cozy Grand Room 1-bedroom apartment with WiFi, AC in charming Winter Haven
Apartment
Winter Haven, FL, 33884, United States
2.3k from Winter Pines Golf Course center

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

1 Bedroom4 Guests
New to Booking
$144
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
4.0k from Winter Pines Golf Course 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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The Poolside Escape
The Poolside Escape
House
Winter Haven, FL, 33884, United States
2.4k from Winter Pines Golf Course center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$245
Average price / night
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Lakefront Retreat In Winterset
Lakefront Retreat In Winterset
House
Winter Haven, FL, USA
4.6k from Winter Pines Golf Course center

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

1 Bedroom6 Guests
New to Booking
$117
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
2.5k from Winter Pines Golf Course 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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3Bed 2Bath Spacious-LakeHomeAceLoc4milesLEGOLAND
3Bed 2Bath Spacious-LakeHomeAceLoc4milesLEGOLAND
House
Cypress Gardens, FL, USA
4.8k from Winter Pines Golf Course 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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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
2.5k from Winter Pines Golf Course 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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1Bed 1Bath Container Home Centrally Located
1Bed 1Bath Container Home Centrally Located
Ski Chalet
Cypress Gardens, FL, USA
4.8k from Winter Pines Golf Course 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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Casa Inman – 3BR Luxury Stay Minutes from Legoland
Casa Inman – 3BR Luxury Stay Minutes from Legoland
Villa
Winter Haven, FL, 33881, United States
2.6k from Winter Pines Golf Course center

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

3 Bedrooms10 Guests
8.4

Very Good

5 reviews

$248
Average price / night
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The Luxury Lakehouse
The Luxury Lakehouse
House
Winter Haven, FL, USA
5.1k from Winter Pines Golf Course center

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

3 Bedrooms7 Guests
7.7

Good

3 reviews

$307
Average price / night
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John Shirley's Retreat
John Shirley's Retreat
House
Winter Haven, FL, 33884, United States
2.8k from Winter Pines Golf Course center

AC, Barbecue, Dryer, Free Parking, Heater, Laundry, Microwave, No Smoking, Pool

3 Bedrooms8 Guests
New to Booking
$319
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
5.3k from Winter Pines Golf Course 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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Family Vacation Home · 8 Minutes from Legoland Florida
Family Vacation Home · 8 Minutes from Legoland Florida
Villa
Winter Haven, FL, 33884, United States
3.0k from Winter Pines Golf Course center

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

3 Bedrooms7 Guests
10.0

Exceptional

3 reviews

$342
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
5.4k from Winter Pines Golf Course 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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Family Winter Haven Retreat w/ Pool & Game Room
Family Winter Haven Retreat w/ Pool & Game Room
House
Winter Haven, FL, 33884, United States
3.0k from Winter Pines Golf Course center

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

3 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$274
Average price / night
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Luxury 3BR with Private POOL • 4 MIN to LEGOLAND • GAME ROOM & FULL KITCHEN.
Luxury 3BR with Private POOL • 4 MIN to LEGOLAND • GAME ROOM & FULL KITCHEN.
House
Winter Haven, FL, 33884, United States
3.1k from Winter Pines Golf Course center

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

3 Bedrooms8 Guests
New to Booking
$354
Average price / night
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Relaxing Retreat with Game Room + Massage Chair+ Fire Pit + Wood Fire Pizza Oven
Relaxing Retreat with Game Room + Massage Chair+ Fire Pit + Wood Fire Pizza Oven
House
Dundee, FL, 33838, United States
3.3k from Winter Pines Golf Course center

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

3 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$172
Average price / night
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3 bdrm Lakefront home in Dundee, FL. 7m to Lego Land, 28m to Disney Wild Kingdom
3 bdrm Lakefront home in Dundee, FL. 7m to Lego Land, 28m to Disney Wild Kingdom
House
Dundee, FL, 33838, United States
3.4k from Winter Pines Golf Course center

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

3 Bedrooms6 Guests
New to Booking
$159
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
3.4k from Winter Pines Golf Course 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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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
3.5k from Winter Pines Golf Course 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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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 Winter Pines Golf Course.

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Frequently Asked Questions

You can explore 309 verified vacation rentals in Winter Pines Golf Course. 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 Winter Pines Golf Course 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 Winter Pines Golf Course 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 Winter Pines Golf Course welcome pets. Currently, 29 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 Winter Pines Golf Course often include amenities such as Fireplace/Heating, Bedding/Linens, and Laundry. 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.