Vacation Rentals in Orwin Manor, FL: Compare 10+ Sites & Save

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694 Best Vacation Rentals in Orwin Manor (Starting from $68)

Roy's guest house
Roy's guest house
House
Orlando, FL, USA
0.7k from Orwin Manor center

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

1 Bedroom2 Guests
9.9

Exceptional

83 reviews

$117
Average price / night
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3-bedroom Bungalow in Welcoming Winter Park with WiFi, AC
3-bedroom Bungalow in Welcoming Winter Park with WiFi, AC
House
Orlando, FL, 32803, United States
0.6k from Orwin Manor center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$450
Average price / night
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Fire Pit + Grill + 2MI to DT Orlando
Fire Pit + Grill + 2MI to DT Orlando
House
Orlando, FL, USA
1.1k from Orwin Manor center

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

3 Bedrooms6 Guests
8.0

Good

1 reviews

$349
Average price / night
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Cozy 2b/2b Duplex Home minutes from near Advent hospital & Rollins college
Cozy 2b/2b Duplex Home minutes from near Advent hospital & Rollins college
House
Orlando, FL, 32804, United States
0.6k from Orwin Manor center

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

2 Bedrooms4 Guests
New to Booking
$175
Average price / night
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Tiny Cottage - 3 MI to Downtwn w Grill & Hammocks
Tiny Cottage - 3 MI to Downtwn w Grill & Hammocks
House
Orlando, FL, USA
1.2k from Orwin Manor center

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

1 Bedroom2 Guests
7.3

Good

3 reviews

$151
Average price / night
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Modern Mediterranean Oasis
Modern Mediterranean Oasis
House
Winter Park, FL, 32789, United States
0.6k from Orwin Manor center

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

3 Bedrooms8 Guests
New to Booking
$253
Average price / night
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Tiny Home w MIL suite - 3 MI to DT
Tiny Home w MIL suite - 3 MI to DT
House
Orlando, FL, USA
1.2k from Orwin Manor center

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

3 Bedrooms7 Guests
New to Booking
$478
Average price / night
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Elegant & Spacious Historic Winter Park Home with Pool + Spa
Elegant & Spacious Historic Winter Park Home with Pool + Spa
House
Winter Park, FL, 32789, United States
0.7k from Orwin Manor center

AC, Dryer, Extra Bed, Fireplace, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
New to Booking
$271
Average price / night
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LUXURY 5bd 4ba w Jacuzzi tub Winter Park CP Orlando Gem
LUXURY 5bd 4ba w Jacuzzi tub Winter Park CP Orlando Gem
Villa
Orlando, FL, USA
1.3k from Orwin Manor center

Luxury, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay

5 Bedrooms22 Guests
New to Booking
$703
Average price / night
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Cheerful and stylish 2-bedroom with parking, centrally located
Cheerful and stylish 2-bedroom with parking, centrally located
House
Winter Park, FL, 32789, United States
0.7k from Orwin Manor center

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

2 Bedrooms4 Guests
New to Booking
$161
Average price / night
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Winter Park Gem 2BR Near Parks 3MI to Downtown
Winter Park Gem 2BR Near Parks 3MI to Downtown
House
Orlando, FL, USA
1.4k from Orwin Manor center

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

2 Bedrooms4 Guests
New to Booking
$286
Average price / night
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Private Poolside Guest House In Winter Park/Orlando
Private Poolside Guest House In Winter Park/Orlando
House
Winter Park, FL, 32789, United States
0.8k from Orwin Manor center

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

1 Bedroom4 Guests
8.0

Good

2 reviews

$147
Average price / night
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2 MI to DT Orlando & Winter Park
2 MI to DT Orlando & Winter Park
House
Orlando, FL, USA
1.5k from Orwin Manor center

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

2 Bedrooms4 Guests
9.0

Fabulous

4 reviews

$227
Average price / night
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The beautiful Melrose Cottage - 25% monthly rental
The beautiful Melrose Cottage - 25% monthly rental
House
Winter Park, FL, 32789, United States
0.9k from Orwin Manor center

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

2 Bedrooms4 Guests
New to Booking
$170
Average price / night
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Luxury Tiny Home 2 Miles from Downtown Orlando
Luxury Tiny Home 2 Miles from Downtown Orlando
House
Orlando, FL, USA
1.5k from Orwin Manor center

Internet, Air Conditioner, Security/Safety, Parking, Fireplace/Heating, Child Friendly

1 Bedroom2 Guests
8.6

Fabulous

12 reviews

$165
Average price / night
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Funky Remodeled Otown Bungalow Sleeps 8
Funky Remodeled Otown Bungalow Sleeps 8
House
Winter Park, FL, 32789, United States
1.0k from Orwin Manor center

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

2 Bedrooms8 Guests
New to Booking
$269
Average price / night
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Downtown Groovy Studio
Downtown Groovy Studio
Apartment
Orlando, FL, USA
1.6k from Orwin Manor center

Apartments, Cheap, Accommodations, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom4 Guests
8.7

Fabulous

15 reviews

$169
Average price / night
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Modern, fabulous two-bedroom with parking in Winter Park
Modern, fabulous two-bedroom with parking in Winter Park
House
Winter Park, FL, 32789, United States
1.0k from Orwin Manor center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$161
Average price / night
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Private Patio College Park Cottage in Orlando!
Private Patio College Park Cottage in Orlando!
House
Orlando, FL, USA
1.8k from Orwin Manor center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Vacation rentals

2 Bedrooms4 Guests
New to Booking
$68
Average price / night
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Cozy home 5min to Park Ave and Downtown Orlando
Cozy home 5min to Park Ave and Downtown Orlando
House
Winter Park, FL, 32789, United States
1.1k from Orwin Manor center

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

2 Bedrooms6 Guests
New to Booking
$267
Average price / night
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Charming home @wp. Patio +Gazebo. close to highwys
Charming home @wp. Patio +Gazebo. close to highwys
House
Winter Park, FL, 32789, United States
1.2k from Orwin Manor center

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

2 Bedrooms7 Guests
7.0

Good

2 reviews

$223
Average price / night
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Private Luxury Pool / Smart-home
Private Luxury Pool / Smart-home
House
Orlando, FL, 32804, United States
1.2k from Orwin Manor 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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THE CLOUD 9 SUITE
THE CLOUD 9 SUITE
House
Winter Park, FL, 32789, United States
1.2k from Orwin Manor center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

2 Bedrooms2 Guests
New to Booking
$208
Average price / night
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Modern 3BR Duplex | Kitchen, Wi-Fi & Pet-Friendly
Modern 3BR Duplex | Kitchen, Wi-Fi & Pet-Friendly
House
Orlando, FL, 32803, United States
1.3k from Orwin Manor center

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

3 Bedrooms6 Guests
New to Booking
$172
Average price / night
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Tiny home w/outdoor kitchen & studio suite
Tiny home w/outdoor kitchen & studio suite
House
Orlando, FL, 32804, United States
1.3k from Orwin Manor center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$396
Average price / night
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Mills House @WP. Sleeps 11 Renovated. Queen beds
Mills House @WP. Sleeps 11 Renovated. Queen beds
House
Winter Park, FL, 32789, United States
1.3k from Orwin Manor center

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

3 Bedrooms11 Guests
8.0

Good

2 reviews

$303
Average price / night
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Triplex Sleeps17 CollegePark Golf 5min to Downtown
Triplex Sleeps17 CollegePark Golf 5min to Downtown
House
Orlando, FL, 32804, United States
1.4k from Orwin Manor center

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

4 Bedrooms16 Guests
New to Booking
$864
Average price / night
Check Availability

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 Orwin Manor.

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Frequently Asked Questions

You can explore 694 verified vacation rentals in Orwin Manor. 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 Orwin Manor vary depending on the season, property size, and location. Rates typically start from around $68 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 Orwin Manor 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 Orwin Manor welcome pets. Currently, 48 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 Orwin Manor often include amenities such as Fireplace/Heating, Laundry, and Wellness Facilities. 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.