Winter Park, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Winter Park, Florida on RentalSaver.com!

Winter Park Rentals

From $140 per night (USD)
VRBO
Stay near Winter Park action at our 2-bedroom apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
In the heart of Winter Park, this charming 2-bedroom apartment offers non-stop chances for unwinding and exploring. Unwi ...
From $140 per night (USD)
VRBO
From $190 per night (USD)
Expedia
New Renovated House Near Everything
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Lovely comfortable and clean home with large “zin” yard in an area that is near the best of the best: Restaurants, Whole ...
From $190 per night (USD)
Expedia
From $186 per night (USD)
VRBO
Charming Clean Home near East End Market Large fenced yard - 25% off thirty days
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Winter Park home ready for your event, vacation or executive rental. Updated kitchen, granite countertops, wood floors, ...
From $186 per night (USD)
VRBO
From $122 per night (USD)
Expedia
Walk The Downtown Village of Winter Park!!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This is a downstairs end apartment with a back door that opens directly onto the pool deck near the hot tub. The apartme ...
From $122 per night (USD)
Expedia
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VRBO
Winter Park Pool Home 4 beds 2 bath
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Centrally located. Quiet neighborhood. Swimming pool with diving board and lots of toys, floaties. Pool table recently u ...
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VRBO
From $248 per night (USD)
Expedia
Stroll to Park Avenue from Vintage Lake-View House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This cozy, quaint Winter Park home was built in 1925. The house has updated appliances and plenty of space. There are tw ...
From $248 per night (USD)
Expedia
From $373 per night (USD)
VRBO
Casa Feliz
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spacious and comfortable 3 bedroom 2 bathroom home with a fully enclosed pool in Maitland. Very quiet cul-de-sac with pl ...
From $373 per night (USD)
VRBO
From $176 per night (USD)
Expedia
Charming Winter Park 3 Bedroom Villa with Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
This villa is centrally located in East Winter Park just off 436 between Aloma and Howell Branch Road with easy access t ...
From $176 per night (USD)
Expedia
From $158 per night (USD)
VRBO
Breezy Pool Home!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our Breezy Winter Park Home where you can relax and enjoy! The home is situated in a short drive to Downtown ...
From $158 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Comfy Home in Winter Park, can accommodate up 6 guests!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our home is located in Winter Park and can serve as a central base to live like a local. You can enjoy all of the great ...
From $267 per night (USD)
Expedia
From $139 per night (USD)
VRBO
Three Blocks to Park Ave, 2 Blocks to WP Village!!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two block ...
From $139 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Best Winter Park Home close to Rollins College, Advent Health & Park Avenue !
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Beautiful furnished and fully equipped kitchen 4-bedroom, 3-bath home which sits on a large fenced corner lot in a high ...
From $353 per night (USD)
Expedia
From $186 per night (USD)
VRBO
A comfortable home close to the city, yet tucked away from the noise.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Perfect for those who want to kick back as well as those who are ready for Orlando fun.... Theme parks, beaches, shoppin ...
From $186 per night (USD)
VRBO
From $401 per night (USD)
Expedia
Casa Bella
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Casa Bella offers new fixtures and equipment . A double car garage . 3 King size master bedrooms with their own full bat ...
From $401 per night (USD)
Expedia
$Mid-Century Modern Gem Near Downtown\/Winter Park\/Baldwin Park$
From $180 per night (USD)
VRBO
Mid-Century Modern Gem Near Downtown\/Winter Park\/Baldwin Park
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Recent renovations makes this mid-century modern cottage feel like a dream and you can't beat the location! Cozy and inv ...
From $180 per night (USD)
VRBO
Click For Pricing
Expedia
A DEAL By The Month! Walk to Rollins & Park Ave
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
It's your own private one-room structure with a private entrance next to a parking space. It's much like a hotel room in ...
Click For Pricing
Expedia
From $90 per night (USD)
VRBO
17'coachman clipper tiny travel trailer
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This little 17' narrow travel trailer is perfect for those that want to "camp" for a few days with out having to set up ...
From $90 per night (USD)
VRBO
From $76 per night (USD)
Expedia
Lakefront Luxury Furnished Split Floor Plan First Floor Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
You will enjoy lake front living on Lake Howell, a 500 acre fishing, sailing and skiing lake. Large first floor 3 bedroo ...
From $76 per night (USD)
Expedia
From $281 per night (USD)
VRBO
You're Pampered Here - Just 3 Blocks From Park Avenue!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Modern, clean and unique. Fastest internet speed available: 139MBPS download and 21.5 MBPS upload! Second floor penthous ...
From $281 per night (USD)
VRBO
From $152 per night (USD)
Expedia
Mid Century Modern Cottage in The Heart of Winter Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Furnished Mid Century Modern Short/Long term rental located in charming Olde Winter Park. Two bedrooms and one and half ...
From $152 per night (USD)
Expedia
$Private Poolside Guest House In Winter Park\/Orlando$
From $147 per night (USD)
VRBO
Private Poolside Guest House In Winter Park\/Orlando
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Beautiful and comfortable two-story cottage/detached guest house, centrally-located within an historic neighborhood. Loc ...
From $147 per night (USD)
VRBO
From $201 per night (USD)
Expedia
Winter Park Oasis
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Your backyard oasis awaits you, with queen size 10in memory foam swing mattress, full outdoor kitchen, 65in TV along wit ...
From $201 per night (USD)
Expedia
From $86 per night (USD)
VRBO
Private Patio: College Park Cottage in Orlando!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Pets Welcome w/ Fee | Furnished Patio | Shaded Property Nestled just 3 miles from downtown, this welcoming 2-bedroom, 1 ...
From $86 per night (USD)
VRBO
$8th Green Cottage \A relaxing Oasis in the city\ Guesthouse$
From $161 per night (USD)
Expedia
8th Green Cottage \"A relaxing Oasis in the city\" Guesthouse
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The 8th Green Cottage is a relaxing oasis in the heart of Orlando. Located less than 10 minutes from downtown. Sitting o ...
From $161 per night (USD)
Expedia
Click For Pricing
VRBO
Winter Park Getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Simplicity at its finest. I host like I live and like I like to be hosted- with chocolates and snacks and fluffy towels ...
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VRBO
From $349 per night (USD)
Expedia
Cheerful 4-bedroom with large and lush backyard
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Your family will be close to everything when you stay at this centrally-located place. Close to multiple interstate entr ...
From $349 per night (USD)
Expedia
From $244 per night (USD)
VRBO
Cute bungalow minutes walk from Park Avenue.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Just what you have been waiting for; beautiful cottage home in the heart of Winter Park! 2 bedroom/2 bath only steps aw ...
From $244 per night (USD)
VRBO
$Cottage on Cornell - Quaint & Cozy w\/Outdoor Kitchen$
Click For Pricing
Expedia
Cottage on Cornell - Quaint & Cozy w\/Outdoor Kitchen
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
Newly renovated guest suite using original reclaimed materials to create a modern vintage farmhouse vibe. Centrally loca ...
Click For Pricing
Expedia
From $379 per night (USD)
VRBO
Casa Winter Park
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casa Winter Park accommodates the need for personal space while enjoying, at the same time, the gathering with several f ...
From $379 per night (USD)
VRBO
$Modern Elegance In The Heart Of Winter Park - 2 beds\/2 baths$
From $185 per night (USD)
Expedia
Modern Elegance In The Heart Of Winter Park - 2 beds\/2 baths
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Location!!! Beautifully appointed 2 bedroom, 2 bath second floor apartment overlooking a beautiful pool area with balcon ...
From $185 per night (USD)
Expedia
From $139 per night (USD)
VRBO
Cute Guest House In Winter Park Minutes From Downtown in Car
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy our guest house and the new space we created in Oct 2015! The guest house has a kitchenette with two glass burners ...
From $139 per night (USD)
VRBO
$Old World Charm of College Park\/Winter Park$
From $198 per night (USD)
Expedia
Old World Charm of College Park\/Winter Park
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcoming and spacious home located in a highly sought after College Park / Winter Park district of Central Florida. It' ...
From $198 per night (USD)
Expedia
From $156 per night (USD)
VRBO
Mid Century Luxury, 1 block from Park Ave (#3)
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This 2nd floor apartment is nestled under oaks on a quiet cobblestone street in downtown Winter Park. There are only 3 u ...
From $156 per night (USD)
VRBO
From $156 per night (USD)
Expedia
Mid Century Luxury, 1 block from Park Ave (#2)
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This ground floor apartment is nestled under oaks on a cobblestone street in downtown Winter Park. There are only 3 unit ...
From $156 per night (USD)
Expedia
Click For Pricing
VRBO
Stunning Orlando Getaway
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
The whole group will enjoy easy access to everything from this centrally located Orlando location. This 1950s beautifull ...
Click For Pricing
VRBO
From $164 per night (USD)
Expedia
Modern Garden Suite!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The space is a newly built 600+ sq ft Modern Chic style home, located in The Audubon Park Garden District! Enjoy the con ...
From $164 per night (USD)
Expedia
From $92 per night (USD)
VRBO
Winter Park charm. Close to Park Ave
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Private 2 bedroom guest suite with its own entry and a separate sitting room. Tandem bedroom include 1 queen sized bed ...
From $92 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Stylish Boutique Guest house in Winter Park
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Indulge the senses in the calming aesthetics of this newly constructed guest house. The residence features room for 4 g ...
From $204 per night (USD)
Expedia
From $125 per night (USD)
VRBO
Light, Bright and Full of Delight! 2 Blocks to Park Ave
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy this PRIVATE and Sparkling clean entire home, first floor 2 bedroom/1 full bath luxury apartment near Park Avenue! ...
From $125 per night (USD)
VRBO
$Mills 50 District\/Audobon Park Area 2 Bedroom$
From $156 per night (USD)
Expedia
Mills 50 District\/Audobon Park Area 2 Bedroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Two bedroom, one bath 1/2 duplex in prime area of Orlando. Big bedroom has queen bed. Smaller bedroom has a twin and a f ...
From $156 per night (USD)
Expedia
From $137 per night (USD)
VRBO
Cottage Retreat in the City
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
QUICK LOOK Newly Constructed, 1-Bedroom Cottage in College Park, a quaint downtown Orlando neighborhood Available Night ...
From $137 per night (USD)
VRBO
$☀️ King Condo w\/ Sunroom, Lakeside Pool and Waterfront Park$
From $133 per night (USD)
Expedia
☀️ King Condo w\/ Sunroom, Lakeside Pool and Waterfront Park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to beautiful Winter Park, Florida and your home away from home in our trendy, super-convenient 1/1 King bed ...
From $133 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Modern Mediterranean Oasis
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Warm and stylish getaway. Very spacious bedrooms open dining and family room. Relax outside with beautifully lit paved p ...
From $254 per night (USD)
VRBO
From $375 per night (USD)
Expedia
Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
One month minimum to rent (30 nights). A hidden gem, this meticulous sun-filled 3 BR + Office/2.5 bath home offers ult ...
From $375 per night (USD)
Expedia
$Top 1% College Park GuestHouse Villa\/Oasis - Mins to DT ORL\/Winter Park & Eola$
From $166 per night (USD)
VRBO
Top 1% College Park GuestHouse Villa\/Oasis - Mins to DT ORL\/Winter Park & Eola
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
***Update January 2025*** EV Level 2 Charger FREE to our guests. 9X faster than Level 1. Located adjacent our Guest park ...
From $166 per night (USD)
VRBO
From $144 per night (USD)
Expedia
Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This is a downstairs end apartment with a back door that opens directly onto the pool deck near the hot tub. The apartme ...
From $144 per night (USD)
Expedia
$Just 3 Blocks to Park Ave Shops\/ Restaurants, 2 From The Winter Park Village!$
From $241 per night (USD)
VRBO
Just 3 Blocks to Park Ave Shops\/ Restaurants, 2 From The Winter Park Village!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Modern, clean and unique. Second floor penthouse unit overlooking the pool area. Gorgeous acacia wood floors, quartz c ...
From $241 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Modern 2BR Lake House in Exclusive Area – No Smoking
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled in prestigious Maitland neighborhood, this stylish and comfortable retreat offers the perfect blend of relaxatio ...
From $235 per night (USD)
Expedia
From $213 per night (USD)
VRBO
Family Friendly home with Fenced in Backyard to enjoy with kids & pets
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This beautiful 3 bedroom, 2 full bathrooms home is located in a lovely and quiet community. Close to shops, restaurants ...
From $213 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Charming home 3 blocks from historic Park Avenue & one block from Lake Virginia
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Open kitchen / family room with dining area to comfortable seat 4, dining room and living room, screened in porch for wa ...
From $314 per night (USD)
Expedia
$Private Luxury Pool \/ Smart-home$
From $338 per night (USD)
VRBO
Private Luxury Pool \/ Smart-home
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Owners have freshly renovated September 2023 Investing over ($75,000) adding the following - Brand new single slope met ...
From $338 per night (USD)
VRBO
From $169 per night (USD)
Expedia
Luxury Living Just 3 Blocks From Park Ave!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful Acacia wood flooring, with marble in the bathrooms and porcelain tile in the kitchen. Quartz countertops, ceil ...
From $169 per night (USD)
Expedia
From $206 per night (USD)
VRBO
Great Family Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Our home has high quality furniture, linens, cookware and tableware for your family dinners. There are large and small ...
From $206 per night (USD)
VRBO
Click For Pricing
Expedia
Amazing College Park private walled in estate
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Amazing private Mediterranean walled estate located across from the historic DubsDread golf course! Centrally located in ...
Click For Pricing
Expedia
From $281 per night (USD)
VRBO
Amazing location- walk to everything
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Entire Private Home - 2 bed 2 bath fully furnished unit located just one block from Park Ave in Winter Park. ***Several ...
From $281 per night (USD)
VRBO
From $304 per night (USD)
Expedia
★Modern DT Home★King Bed☀️Patios✔Long Stays⚡️WiFi★
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy your peaceful stay in a quiet neighborhood in this beautiful Mid-Century modern townhome, just 8 minutes from dow ...
From $304 per night (USD)
Expedia
$Lakefront Condo w\/ Sunroom, Office, & Lakeside Pool$
From $133 per night (USD)
VRBO
Lakefront Condo w\/ Sunroom, Office, & Lakeside Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to beautiful Winter Park, Florida and your home away from home in your lakeside, super-convenient 1 bedroom /1 h ...
From $133 per night (USD)
VRBO
From $115 per night (USD)
Expedia
LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This duplex unit is cozy and comfortable. It's updated with all new appliances, is tastefully decorated and has very com ...
From $115 per night (USD)
Expedia
From $120 per night (USD)
VRBO
Cozy Comfort Just 2 Blocks From Park Ave!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This duplex unit is cozy and comfortable. It's updated with all new appliances, is tastefully decorated and has very com ...
From $120 per night (USD)
VRBO
Click For Pricing
Expedia
NEW! ☀Bungalow+Patio+FirePit! Close to Everything!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You will love it here! This trendy winter park home will feel like home! Well equipped with all your essentials (Soaps+ ...
Click For Pricing
Expedia
$Contemporary Award Winning Hotel w\/Rooftop Close to Parks & Rollins College$
From $385 per night (USD)
VRBO
Contemporary Award Winning Hotel w\/Rooftop Close to Parks & Rollins College
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our 323 square foot King Room is appointed with handsome contemporary furnishings, including an armoire, mini fridge, fl ...
From $385 per night (USD)
VRBO
From $385 per night (USD)
VRBO
ADA Compliant Room - Contemporary Furnishings - Rooftop Pool - Close to Parks
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our Classic King ADA is wheelchair-accessible. The room is appointed with handsome contemporary furnishings, including a ...
From $385 per night (USD)
VRBO
From $419 per night (USD)
VRBO
Private Balcony in Award Winning Hotel, Roof-top Pool, Close to Rollins College
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Classic King with Balcony room measures 323 square feet and has the added feature of a balcony with French doors tha ...
From $419 per night (USD)
VRBO
From $386 per night (USD)
VRBO
Award Winning Boutique Hotel Close to Parks & Rollins College, Rooftop Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our Classic Queen room is 358 square feet and appointed with two pillowtop Queen size beds, luxury linens and handsome c ...
From $386 per night (USD)
VRBO
$Private Balcony - Award Winning Accommodations w\/Rooftop Pool, Close to Parks!$
From $420 per night (USD)
VRBO
Private Balcony - Award Winning Accommodations w\/Rooftop Pool, Close to Parks!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our Classic Queen with Balcony room is 358 square feet and appointed with two pillowtop Queen size beds, luxury linens a ...
From $420 per night (USD)
VRBO
From $426 per night (USD)
VRBO
Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Our Premier ADA Queen is a larger room at 448 square feet and is wheelchair-accessible. The room features an additional ...
From $426 per night (USD)
VRBO
$Large Room Award Winning Hotel w\/Rooftop Pool - Close to Parks & Rollins College$
From $489 per night (USD)
VRBO
Large Room Award Winning Hotel w\/Rooftop Pool - Close to Parks & Rollins College
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our Parlor King is a larger room at 435 square feet and features a separate Parlor seating area with a sleeper sofa and ...
From $489 per night (USD)
VRBO
$ADA Compliant Room in Award Winning Hotel w\/Rooftop Pool - Close to Parks!$
From $441 per night (USD)
VRBO
ADA Compliant Room in Award Winning Hotel w\/Rooftop Pool - Close to Parks!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Our Premier ADA Queen is a larger room at 448 square feet and is wheelchair-accessible. The room features an additional ...
From $441 per night (USD)
VRBO
From $219 per night (USD)
VRBO
CHARMING - Cozy Retreat Near Lake Killarney in Winter Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come and stay awhile at the Killarney Retreat, built in the 50s, tucked away from the hub of city, yet just a short driv ...
From $219 per night (USD)
VRBO
From $199 per night (USD)
Expedia
Temporary living that feels like home where you can relax and be yourself.
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Fully furnished, charming and comfortable, 4 bedroom - 2 bath, short-term home has new linens, new beds (1 King, 2 queen ...
From $199 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Winter Park Oasis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy your stay at the Winter Park Oasis! This cozy 2 bedroom private unit, is in a charming and historic neighborhood! ...
From $172 per night (USD)
VRBO
From $200 per night (USD)
Expedia
GREAT LOCATION 🏡
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Location, location, location - this immaculate Olde Winter Park home is ready for you to relax and enjoy Winter Park and ...
From $200 per night (USD)
Expedia
From $221 per night (USD)
VRBO
Ideal Location, Charming 4 bedroom home w Pool, fenced yard, 40% off thirty days
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Traditional Old Winter Park home ready for your event, special occasion, vacation, wedding, golf weekend, or executive r ...
From $221 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Winter Park Bungalow & Outdoor Oasis - Rollins College, Park Ave & Fenced Yard
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This charming bungalow in the heart of Winter Park's upscale Forest Hills neighborhood is the perfect retreat for your n ...
From $220 per night (USD)
Expedia
Click For Pricing
VRBO
By the Sea Style Condo
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Welcome to your home away from home. This rental unit is located just 10 minutes from Downtown Orlando and is a 25-30 mt ...
Click For Pricing
VRBO
Click For Pricing
Expedia
1 bed, 1 bath college park gem
Bedrooms:
1
Bathrooms:
2
Sleeps:
28
My home is on a quiet street nestled in the Dubsdread Golf Course, less than 10 minutes from downtown Orlando and Winter ...
Click For Pricing
Expedia
From $161 per night (USD)
VRBO
Coastal Feel - Modern Appeal
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2 bedroom 2 bath, 1350 sqft detached home Family friendly layout with master bedroom suite, shared bedroom (2 twin beds) ...
From $161 per night (USD)
VRBO
Click For Pricing
Expedia
Cozy Getaway
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
This is a two bedroom 2 1/2 bath condo located near downtown Orlando minutes away from shopping centers & restaurants. O ...
Click For Pricing
Expedia
From $427 per night (USD)
VRBO
Greatest location! Condo with private yard!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Location, Location, Location!!! Greatest location! Well appointed condo -one block from Park Avenue! This is a Downstair ...
From $427 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Modern and fabulous tropical oasis, central to everything!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Make memories at this unique and family-friendly property in the heart of Audubon Park. Hang out in a tropical garden sh ...
From $240 per night (USD)
Expedia
Click For Pricing
VRBO
Cozy Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
...
Click For Pricing
VRBO
From $155 per night (USD)
Expedia
Luxury Tiny Home -2 MI to DT Orlando & Winter Park
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: Enjoy your stay in a stylish, new construction tiny home in one of Orlando's best neighborhoods, College Park. ...
From $155 per night (USD)
Expedia
$Luxury Ranch 2 Master Kg Bed w\/ heated Salted Pool$
From $840 per night (USD)
VRBO
Luxury Ranch 2 Master Kg Bed w\/ heated Salted Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
13
The Luxury Ranch is a tropical getaway in Orlando where life revolves around the sunshine, swimming pool, and airy sunro ...
From $840 per night (USD)
VRBO
From $166 per night (USD)
Expedia
Sunshine Escape Guesthouse ☀
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Clean and comfortable guesthouse centrally located in Orlando. It is perfect for business travelers, baecation for coupl ...
From $166 per night (USD)
Expedia
$Spacious Home w\/Pool & Hot Tub near Downtown Orlando!$
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VRBO
Spacious Home w\/Pool & Hot Tub near Downtown Orlando!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in one of the best neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5 min walk to tons ...
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VRBO
From $138 per night (USD)
Expedia
Very Special HGTV Type 2 bed 1 bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Beautiful 2 bed 1 Bath first floor, fenced in just completely remodeled Condo. Located on 500 Acre fish/ski Lake Howell. ...
From $138 per night (USD)
Expedia
From $162 per night (USD)
VRBO
Modern, fabulous two-bedroom with parking in Winter Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Our newly renovated duplex home is stylish and well-appointed with everything you need for a getaway or a longer visit. ...
From $162 per night (USD)
VRBO
From $209 per night (USD)
Expedia
THE CLOUD 9 SUITE
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
PET FRIENDLY 🐾 Book the Cloud 9 Suite, located in the heart of downtown Winter Park FL and Orlando! Beautifully furnish ...
From $209 per night (USD)
Expedia
From $146 per night (USD)
VRBO
Home Away from Home- Winter Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy our newly renovated home in Winter Park. We are centrally located and within minutes from Rollins College and Park ...
From $146 per night (USD)
VRBO
From $126 per night (USD)
Expedia
Beautiful Direct Fish & Ski Lakefront Town home In N. Orlando with Pool & WiFi
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Direct lake front condo 2 bed 2 ½ bath townhouse w/private boat dock. Includes Electric with Password Protected Spectrum ...
From $126 per night (USD)
Expedia
From $173 per night (USD)
VRBO
Quaint Winter Park East End Market Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to our Winter Park home behind East End Market ! You will fall in love with this area which is full of friendly ...
From $173 per night (USD)
VRBO
From $431 per night (USD)
Expedia
Deck Condo
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Your family will be close to everything when you stay at this centrally-located place. Nestled along the SHORELINE of be ...
From $431 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Casa Jardin
Bedrooms:
6
Bathrooms:
3
Sleeps:
6
3 bedrooms with 3 bathrooms home overlooking an extra large backyard with a mature landscape surrounding the pool area. ...
From $367 per night (USD)
VRBO
Click For Pricing
Expedia
Renovated College Park home Sleeps10 close to WP
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Enjoy a conveniently stylish experience at this centrally-located newly renovated place. This modest concrete block dupl ...
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Expedia
From $230 per night (USD)
VRBO
Mills House @WP. Sleeps 11 Renovated. Queen beds
Bedrooms:
2
Bathrooms:
3
Sleeps:
11
Enjoy a stylish experience at this centrally-located place. MillsHouse is conveniently located for a foodie adventure. T ...
From $230 per night (USD)
VRBO
From $364 per night (USD)
Expedia
3Bdrm Home Near Downtown Orlando and Winter park
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
This stylish place to stay is perfect for group trips! This is a 3 bedroom modern home that is conveniently located near ...
From $364 per night (USD)
Expedia
Click For Pricing
VRBO
Advent health all white unit
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to my charming 2 bedroom 2 bathroom home in the heart of Orlando FL located right of the I4 highway exit Princet ...
Click For Pricing
VRBO
From $136 per night (USD)
Expedia
Quaint Key West Pool Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Historic Winter Park Florida. Central Florida's gem Winter Park is filled with history, whimsy and magic as i ...
From $136 per night (USD)
Expedia
$6 Mi to Downtown Orlando: Quiet Home w\/ Sunroom$
From $132 per night (USD)
VRBO
6 Mi to Downtown Orlando: Quiet Home w\/ Sunroom
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Soak up the Florida sun and explore the Orlando area with ease from this 2-bed, 1-bath vacation rental in Winter Park! Y ...
From $132 per night (USD)
VRBO
From $154 per night (USD)
Expedia
City Charmer
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come stay on the quiet side of Orlando, just a stone throw away to Baldwin Park. This half duplex has 2 bedrooms and 2 f ...
From $154 per night (USD)
Expedia

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Results: 183 Rentals