Vacation Rentals with Private Pool in Winter Park Hospital, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
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  6.  Winter Park Hospital

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56 Best Vacation Rentals with Private Pool in Winter Park Hospital (Starting from $140)

Casa Winter Park
Casa Winter Park
House
Winter Park, FL, 32792, United States
1.1k from Winter Park Hospital 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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Citrus Oasis: 4BR Pool Home
Citrus Oasis: 4BR Pool Home
House
Winter Park, FL, 32792, United States
3.0k from Winter Park Hospital 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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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
3.1k from Winter Park Hospital 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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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
3.1k from Winter Park Hospital 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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Winter Park 3BR Oasis- Private Pool
Winter Park 3BR Oasis- Private Pool
House
Winter Park, FL, 32792, United States
3.4k from Winter Park Hospital 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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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
3.7k from Winter Park Hospital 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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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
3.7k from Winter Park Hospital 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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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
3.7k from Winter Park Hospital 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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*Travel Themed Property with Backyard Oasis*
*Travel Themed Property with Backyard Oasis*
House
Maitland, FL, 32751, United States
3.8k from Winter Park Hospital 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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Casa Jardin
Casa Jardin
House
Maitland, FL, 32751, United States
4.1k from Winter Park Hospital 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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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
4.4k from Winter Park Hospital 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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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
4.4k from Winter Park Hospital 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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Casa Feliz
Casa Feliz
House
Maitland, FL, 32751, United States
4.8k from Winter Park Hospital 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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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
5.1k from Winter Park Hospital 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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Anysel Pool house
Anysel Pool house
House
Orlando, FL, 32807, United States
5.3k from Winter Park Hospital 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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Modern Tropical Pool Home ⭐️
Modern Tropical Pool Home ⭐️
House
Orlando, FL, 32817, United States
5.4k from Winter Park Hospital 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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Private Luxury Pool / Smart-home
Private Luxury Pool / Smart-home
House
Orlando, FL, 32804, United States
5.5k from Winter Park Hospital 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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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
5.7k from Winter Park Hospital 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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Casa Bella
Casa Bella
House
Maitland, FL, 32751, United States
5.8k from Winter Park Hospital center

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

5 Bedrooms8 Guests
9.8

Exceptional

163 reviews

$381
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
5.8k from Winter Park Hospital 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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Luxury Ranch 2 Master Kg Bed w/ heated Salted Pool
Luxury Ranch 2 Master Kg Bed w/ heated Salted Pool
House
Orlando, FL, 32804, United States
5.8k from Winter Park Hospital center

Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms13 Guests
10.0

Exceptional

11 reviews

$1001
Average price / night
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Cozy 4/2, King Beds, Pergola & Hot Tub, Local Pool!
Cozy 4/2, King Beds, Pergola & Hot Tub, Local Pool!
House
Casselberry, FL, 32707, United States
6.2k from Winter Park Hospital center

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

4 Bedrooms13 Guests
9.6

Exceptional

15 reviews

$356
Average price / night
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Wana Chill Spot  w/ Pool, Spa, Bar ,Ping Pong, BBQ
Wana Chill Spot w/ Pool, Spa, Bar ,Ping Pong, BBQ
House
Casselberry, FL, 32707, United States
6.4k from Winter Park Hospital center

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

3 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$340
Average price / night
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The Soundwave Retreat 🌴 Pool, Spa & Golf Oasis
The Soundwave Retreat 🌴 Pool, Spa & Golf Oasis
House
Casselberry, FL, 32707, United States
6.5k from Winter Park Hospital center

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

4 Bedrooms14 Guests
10.0

Exceptional

6 reviews

$540
Average price / night
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Traveler's Dream: Refresh & Recharge Poolside
Traveler's Dream: Refresh & Recharge Poolside
Apartment
Casselberry, FL, 32707, United States
6.7k from Winter Park Hospital center

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

1 Bedroom2 Guests
9.4

Superb

10 reviews

$140
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
6.8k from Winter Park Hospital 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
6.8k from Winter Park Hospital 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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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 Park Hospital.

Where to stay in Winter Park Hospital? Best neighborhoods & areas

Winter Park Hospital Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 56 verified vacation rentals with a private pool in Winter Park Hospital. 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 Park Hospital vary depending on the property size, location, and travel season. Rates typically start from around $140 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 Park Hospital also welcome pets. Currently, 26 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 Park Hospital 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 Park Hospital 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.