Vacation Rentals with Private Pool in Winter Pines Golf Club, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Orlando
  6.  Winter Pines Golf Club

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60 Best Vacation Rentals with Private Pool in Winter Pines Golf Club (Starting from $72)

1-bedroom vacation room just 12 minutes from University of Central Florida
1-bedroom vacation room just 12 minutes from University of Central Florida
Apartment
Orlando, FL, 32807, United States
1.8k from Winter Pines Golf Club center

AC, Barbecue, Breakfast Available, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
9.4

Superb

3 reviews

$177
Average price / night
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Casa Winter Park
Casa Winter Park
House
Winter Park, FL, 32792, United States
1.9k from Winter Pines Golf Club center

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

4 Bedrooms8 Guests
9.8

Exceptional

123 reviews

$380
Average price / night
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Luxury 4BR Home Pool Heat Available Extra charge Hot Tub 2 Grills WiFi
Luxury 4BR Home Pool Heat Available Extra charge Hot Tub 2 Grills WiFi
House
Orlando, FL, 32807, United States
2.5k from Winter Pines Golf Club center

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

4 Bedrooms10 Guests
10.0

Exceptional

18 reviews

$326
Average price / night
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Ideal Location, Charming 4 bedroom home w Pool, fenced yard.
Ideal Location, Charming 4 bedroom home w Pool, fenced yard.
House
Winter Park, FL, 32789, United States
2.9k from Winter Pines Golf Club center

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

4 Bedrooms10 Guests
10.0

Exceptional

112 reviews

$370
Average price / night
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Citrus Oasis: 4BR Pool Home
Citrus Oasis: 4BR Pool Home
House
Winter Park, FL, 32792, United States
3.3k from Winter Pines Golf Club center

AC, Free Parking, Internet, Kitchen, No Smoking, Pool, TV, Washer

4 Bedrooms8 Guests
4.6

Review score

4 reviews

$282
Average price / night
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Anysel Pool house
Anysel Pool house
House
Orlando, FL, 32807, United States
3.3k from Winter Pines Golf Club center

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

3 Bedrooms8 Guests
7.4

Good

3 reviews

$167
Average price / night
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Winter Park 3BR Oasis- Private Pool
Winter Park 3BR Oasis- Private Pool
House
Winter Park, FL, 32792, United States
3.8k from Winter Pines Golf Club center

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

3 Bedrooms6 Guests
New to Booking
$307
Average price / night
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Resort Like Private Pool Waterfront Retreat 4/2 Home in Orlando Weekly discounts
Resort Like Private Pool Waterfront Retreat 4/2 Home in Orlando Weekly discounts
House
Orlando, FL, 32817, United States
3.9k from Winter Pines Golf Club center

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

4 Bedrooms8 Guests
10.0

Exceptional

131 reviews

$279
Average price / night
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Charming 3-bedroom house with WiFi, AC in Winter Park
Charming 3-bedroom house with WiFi, AC in Winter Park
House
Winter Park, FL, 32792, United States
4.0k from Winter Pines Golf Club center

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

3 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$323
Average price / night
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Lakefront Luxury pool 3100sq ft on lake.
Lakefront Luxury pool 3100sq ft on lake.
House
Orlando, FL, 32807, United States
4.3k from Winter Pines Golf Club center

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

5 Bedrooms14 Guests
10.0

Exceptional

10 reviews

$823
Average price / night
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Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
House
Winter Park, FL, 32792, United States
4.3k from Winter Pines Golf Club center

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

3 Bedrooms8 Guests
8.8

Fabulous

30 reviews

$303
Average price / night
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Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.
Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.
House
Winter Park, FL, 32789, United States
4.4k from Winter Pines Golf Club center

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

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$374
Average price / night
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Vibrant Orlando Lakefront Cat Lover's Retreat with Pool & Gardens
Vibrant Orlando Lakefront Cat Lover's Retreat with Pool & Gardens
House
Orlando, FL, 32803, United States
4.5k from Winter Pines Golf Club center

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

4 Bedrooms7 Guests
New to Booking
$200
Average price / night
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Modern Tropical Pool Home ⭐️
Modern Tropical Pool Home ⭐️
House
Orlando, FL, 32817, United States
4.5k from Winter Pines Golf Club center

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

3 Bedrooms6 Guests
9.8

Exceptional

21 reviews

$395
Average price / night
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Winter Park Charmer - Heated Pool Home - Close to everything
Winter Park Charmer - Heated Pool Home - Close to everything
House
Winter Park, FL, 32792, United States
4.8k from Winter Pines Golf Club center

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

4 Bedrooms8 Guests
8.2

Very Good

15 reviews

$281
Average price / night
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Pet friendly 3 Bedroom POOL Home in the Heart of Orlando
Pet friendly 3 Bedroom POOL Home in the Heart of Orlando
House
Orlando, FL, 32807, United States
4.8k from Winter Pines Golf Club center

AC, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

3 Bedrooms7 Guests
9.2

Superb

7 reviews

$329
Average price / night
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4/2.5 Resort-like lake front saltwater pool home
4/2.5 Resort-like lake front saltwater pool home
House
Orlando, FL, 32817, United States
5.2k from Winter Pines Golf Club center

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

4 Bedrooms8 Guests
10.0

Exceptional

32 reviews

$401
Average price / night
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*Travel Themed Property with Backyard Oasis*
*Travel Themed Property with Backyard Oasis*
House
Maitland, FL, 32751, United States
5.4k from Winter Pines Golf Club center

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

6 Bedrooms14 Guests
9.8

Exceptional

37 reviews

$549
Average price / night
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Orlando 3BR Getaway • Wi-Fi + Fun for Families
Orlando 3BR Getaway • Wi-Fi + Fun for Families
House
Orlando, FL, 32825, United States
5.5k from Winter Pines Golf Club center

AC, Arcade, Dryer, Fireplace, Free Parking, Internet, Kitchen, Laundry, Microwave

3 Bedrooms7 Guests
7.0

Good

2 reviews

$250
Average price / night
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Botanical Garden Home-20 min to Disney, 10 Min to Downtown & 40 Min to the beach
Botanical Garden Home-20 min to Disney, 10 Min to Downtown & 40 Min to the beach
House
Orlando, FL, 32825, United States
5.8k from Winter Pines Golf Club center

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

3 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$215
Average price / night
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Casa Jardin
Casa Jardin
House
Maitland, FL, 32751, United States
6.1k from Winter Pines Golf Club center

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

4 Bedrooms6 Guests
9.8

Exceptional

30 reviews

$387
Average price / night
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‼️Relaxing East Orlando Retreat w/ Private Pool
‼️Relaxing East Orlando Retreat w/ Private Pool
House
Orlando, FL, 32825, United States
6.3k from Winter Pines Golf Club center

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

3 Bedrooms6 Guests
9.4

Superb

28 reviews

$286
Average price / night
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Casa Feliz
Casa Feliz
House
Maitland, FL, 32751, United States
6.4k from Winter Pines Golf Club center

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

3 Bedrooms8 Guests
10.0

Exceptional

47 reviews

$366
Average price / night
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Private Luxury Pool / Smart-home
Private Luxury Pool / Smart-home
House
Orlando, FL, 32804, United States
6.5k from Winter Pines Golf Club center

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

3 Bedrooms8 Guests
9.6

Exceptional

77 reviews

$392
Average price / night
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Pet-Friendly Studio in Downtown Orlando • Modern
Pet-Friendly Studio in Downtown Orlando • Modern
House
Orlando, FL, 32812, United States
6.6k from Winter Pines Golf Club center

AC, Extra Bed, Heater, Internet, Microwave, No Smoking, Outdoor Space, Patio, Pool

1 Bedroom2 Guests
8.0

Good

2 reviews

$72
Average price / night
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2BR Family Retreat • Orlando • Full Kitchen
2BR Family Retreat • Orlando • Full Kitchen
House
Orlando, FL, 32812, United States
6.6k from Winter Pines Golf Club center

AC, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, Patio

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$88
Average price / night
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Luxury Lakefront Retreat w Pool, Balcony, Firepit, Dock, Orlando, FL Sleeps 12
Luxury Lakefront Retreat w Pool, Balcony, Firepit, Dock, Orlando, FL Sleeps 12
House
Orlando, FL, 32817, United States
6.7k from Winter Pines Golf Club center

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

4 Bedrooms12 Guests
New to Booking
$752
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 Winter Pines Golf Club.

Where to stay in Winter Pines Golf Club? Best neighborhoods & areas

Winter Pines Golf Club Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 60 verified vacation rentals with a private pool in Winter Pines Golf 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 Winter Pines Golf Club vary depending on the property size, location, and travel season. Rates typically start from around $72 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 Winter Pines Golf Club also welcome pets. Currently, 25 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 Winter Pines Golf Club often include additional features such as Pool, Private Pool, and Wellness Facilities. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Winter Pines Golf 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.