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251 Rentals In Winter Park
United States
Florida
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Winter Park
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Amenities
Pool
Internet
Washer
Fishing
FirePlace
Wheelchair Access
Non Smoking
Yard
TV
Balcony
Patio
Parking
AC
Microwave
No Pets
Jacuzzi
Pet Allowed
Dishwasher
Kitchen
Sauna
Crib
Smoking Allowed
Grill
Cozy Comfort In The Heart of Winter Park!
2
1.0
4
Winter Park Florida Apartment
From $115 per night
(USD)
Three Blocks to Park Ave, 2 Blocks to WP Village!!!
2
1.0
4
Winter Park Florida Apartment
From $120 per night
(USD)
A curated stay in the Historic College Quarter
2
1.0
4
Winter Park Florida Cottage
From $249 per night
(USD)
Best Winter Park Home close to Rollins College, Advent Health & Park Avenue !
4
3.0
12
Winter Park Florida Private vacation home
From $272 per night
(USD)
Winter Park Getaway
1
1.0
4
Winter Park Florida Guest house
Click For Pricing
Cute bungalow minutes walk from Park Avenue.
2
2.0
4
Winter Park Florida Private vacation home
From $194 per night
(USD)
Luxury Villa, 3bed\/2bath Great Location with Pool
3
2.0
9
Winter Park Florida Private vacation home
From $139 per night
(USD)
Mid Century Luxury, 1 block from Park Ave (#3)
2
1.0
5
Winter Park Florida Apartment
From $140 per night
(USD)
Mid Century Luxury, 1 block from Park Ave (#2)
2
1.0
5
Winter Park Florida Apartment
From $138 per night
(USD)
Winter Park charm. Close to Park Ave
2
1.0
4
Winter Park Florida Private vacation home
From $92 per night
(USD)
Stylish Boutique Guest house in Historic Winter Park.
2
1.0
4
Winter Park Florida Apartment
From $150 per night
(USD)
Modern Mediterranean Oasis
3
2.0
8
Winter Park Florida Private vacation home
From $217 per night
(USD)
Best Home by Winter Park Hospital, Rollins College and Park Ave !
3
2.0
10
Winter Park Florida Private vacation home
From $243 per night
(USD)
Luxury Living Just 3 Blocks From Park Ave!!!
2
2.0
4
WINTER PARK Florida Apartment
From $125 per night
(USD)
Amazing location- walk to everything
2
2.0
5
Winter Park Florida Condo
From $356 per night
(USD)
Winter Park Oasis
2
1.0
4
Winter Park Florida Private vacation home
From $150 per night
(USD)
GREAT LOCATION 🏡
3
3.0
6
Winter Park Florida Private vacation home
From $161 per night
(USD)
3 Bedroom Townhome 421120 by Houzlet
3
3.0
6
Winter Park Florida Private vacation home
Click For Pricing
3 Bedroom Condo 441946 by Houzlet
3
4.0
6
Winter Park Florida Condo
Click For Pricing
3 Bedroom Apartment 420428 by Houzlet
3
4.0
6
Winter Park Florida Apartment
Click For Pricing
Home away from home in the heart of charming Winter Park!
2
2.0
4
Winter Park Florida Private vacation home
From $275 per night
(USD)
Little gem apartment
1
1.0
2
Winter Park Florida Apartment
From $175 per night
(USD)
Coastal Chic Custom Winter Park Pool Home, 4400 total sqft of living space.
4
4.0
8
Winter Park Florida Private vacation home
From $335 per night
(USD)
2 Bed 1.5 Bath in Winter Park
2
2.0
4
Winter Park Florida Private vacation home
From $97 per night
(USD)
Ideal Location, Charming Home, Specious Full Lap Pool! 40% Off Monthly Rental
4
2.0
10
Winter Park Florida Private vacation home
From $218 per night
(USD)
Lakefront Condo w\/ Sunroom, Office, & Lakeside Pool
1
1.0
2
Winter Park Florida Condo
From $115 per night
(USD)
Family Friendly
3
2.0
5
Winter Park Florida Private vacation home
From $200 per night
(USD)
Charming home 3 blocks from historic Park Avenue & one block from Lake Virginia
2
2.0
4
Winter Park Florida Private vacation home
From $275 per night
(USD)
Just 3 Blocks to Park Ave Shops\/ Restaurants, 2 From The Winter Park Village!
3
3.0
6
Winter Park Florida Apartment
From $185 per night
(USD)
☀️ King Condo w\/ Sunroom, Lakeside Pool and Waterfront Park
1
1.0
2
Winter Park Florida Condo
From $115 per night
(USD)
Modern Elegance In The Heart Of Winter Park - 2 beds\/2 baths
2
2.0
4
Winter Park Florida Apartment
From $156 per night
(USD)
Mid Century Modern Cottage in The Heart of Winter Park
2
1.0
5
Winter Park Florida Cottage
From $120 per night
(USD)
Chic Lakeside Midcentury Modern Retreat
2
1.0
4
Winter Park Florida Condo
From $116 per night
(USD)
Winter Park Oasis
2
1.0
8
Winter Park Florida Private vacation home
From $175 per night
(USD)
Stroll to Park Avenue from Vintage Lake-View House
2
2.0
6
Winter Park Florida Private vacation home
From $214 per night
(USD)
Total Serenity #2, 2 BDRM, 2 Bath
2
2.0
8
Winter Park Florida Apartment
From $186 per night
(USD)
Tranquil & Tiny house
1
1.0
3
Winter Park Florida Private vacation home
From $135 per night
(USD)
Cute and Cozy Apartment-B 1 Bedroom Duplex
1
1.0
2
Winter Park Florida Apartment
From $145 per night
(USD)
Hidden Oasis #4 2 BDRM, 2 Bath
2
2.0
6
Winter Park Florida Apartment
From $190 per night
(USD)
Peace and the Park #3 -2 BDRM, 2 Bath
2
2.0
4
Winter Park Florida Private vacation home
From $186 per night
(USD)
Home Away from Home- Winter Park
2
2.0
4
Winter Park Florida Private vacation home
From $125 per night
(USD)
Cabana style studio apt\/private garden near Rollins and Park Ave. 1 week minim<br><br>
1
2.0
3
Winter Park Florida Apartment
From $120 per night
(USD)
LUXURY AND LOCATION!!!
2
2.0
5
WINTER PARK Florida Apartment
From $111 per night
(USD)
Newly renovated Cottage in the heart of Winter Park's most desired neighborhood.
2
2.0
4
Winter Park Florida Private vacation home
From $212 per night
(USD)
Waterfront Winter Park Midcentury 4br w\/ Pool
4
4.0
10
Winter Park Florida Private vacation home
From $325 per night
(USD)
Cozy and Chic Winter Park Studio which is conveniently located just for you
1
1.0
2
Winter Park Florida Apartment
From $100 per night
(USD)
LUXURY 𝕄𝕚𝕕 ℂ𝕖𝕟𝕥𝕦𝕣𝕪 𝕄𝕠𝕕𝕖𝕣𝕟 ᴠᴀᴄᴀᴛɪᴏɴ in 𝒲𝒾𝓃𝓉𝑒𝓇 𝒫𝒶𝓇𝓀
3
3.0
8
Winter Park Florida Private vacation home
From $250 per night
(USD)
Charming 2BR\/2BA Winter Park Cottage, steps from Park Ave
2
2.0
6
Winter Park Florida Private vacation home
From $110 per night
(USD)
Cheerful and stylish 2-bedroom with parking, centrally located
2
1.0
4
Winter Park Florida Private vacation home
From $138 per night
(USD)
Modern, fabulous two-bedroom with parking in Winter Park
2
2.0
4
Winter Park Florida Private vacation home
From $138 per night
(USD)
Quaint Winter Park East End Market Home
1
1.0
2
Winter Park Florida Private vacation home
From $149 per night
(USD)
Winter Park Retreat
3
2.0
6
Winter Park Florida Private vacation home
From $299 per night
(USD)
Peaceful Retreat #1 -2B \/2B Apartment
2
2.0
8
Winter Park Florida Apartment
From $186 per night
(USD)
Studio Blue
1.0
Winter Park Florida Apartment
Click For Pricing
Greatest location! Condo with private yard!
2
2.0
4
Winter Park Florida Condo
From $375 per night
(USD)
Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!
2
1.0
4
Winter Park Florida Apartment
From $125 per night
(USD)
CHARMING - Cozy Retreat Near Lake Killarney in Winter Park
2
2.0
6
Winter Park Florida Private vacation home
From $165 per night
(USD)
Walk The Downtown Village of Winter Park!!!
2
1.0
4
Winter Park Florida Apartment
From $105 per night
(USD)
A DEAL By The Month! Walk to Rollins & Park Ave
1
1.0
2
Winter Park Florida Private vacation home
Click For Pricing
You're Pampered Here - Just 3 Blocks From Park Avenue!
3
3.0
6
Winter Park Florida Apartment
From $175 per night
(USD)
Light, Bright and Full of Delight! 2 Blocks to Park Ave
2
1.0
4
Winter Park Florida Apartment
From $120 per night
(USD)
LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!
2
1.0
4
Winter Park Florida Private vacation home
From $117 per night
(USD)
Cozy Comfort Just 2 Blocks From Park Ave!
2
1.0
4
Winter Park Florida Private vacation home
From $115 per night
(USD)
Adorable 1 Bedroom in the perfect location!
1
1.0
2
Winter Park Florida Apartment
From $68 per night
(USD)
Mills House @WP. Sleeps 11 Renovated. Queen beds
3
2.0
11
Winter Park Florida Private vacation home
Click For Pricing
Florida Vacation Rental ~ 6 Mi to Downtown Orlando
2
1.0
4
Winter Park Florida Private vacation home
From $73 per night
(USD)
Comfortable House in the lovely Winter Park, Olando Fl .
3
2.0
6
Winter Park Florida Private vacation home
From $189 per night
(USD)
Are You Ready to Live Like Locals?
4
2.0
4
Winter Park Florida Private vacation home
Click For Pricing
Charming Home Winter Park, Rolliins College, Orlando FL
3
2.0
6
Winter Park Florida Private vacation home
From $151 per night
(USD)
florida my favorite
3
2.0
6
Winter Park Florida Private vacation home
Click For Pricing
Cozy 4-bedroom house with WiFi, AC in peaceful Winter Park
4
3.0
8
Winter Park Florida Private vacation home
From $140 per night
(USD)
Landing at Juno at Winter Park - 3 Bedrooms in Downtown Winter Park
3
3.0
6
Winter Park Florida Apartment
Click For Pricing
Cozy and Sweet Sunshine house
2
1.0
4
Winter Park Florida Private vacation home
From $123 per night
(USD)
Large 1BR\/1BTH guest-house with full kitchen w&d
1
2.0
2
Winter Park Florida Guest house
From $146 per night
(USD)
New LuxattheWin w\/free parking, Walking and Golfing
2
1.0
3
Winter Park Florida Apartment
Click For Pricing
Quaint Key West Pool Home
1
1.0
2
Winter Park Florida Private vacation home
Click For Pricing
☺️Cozy and Close to EVERYTHING!
2
1.0
4
Winter Park Florida Private vacation home
From $150 per night
(USD)
Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.
3
3.0
6
Winter Park Florida Private vacation home
From $325 per night
(USD)
Cheerful 4-bedroom with large and lush backyard
4
3.0
8
Orlando Florida Private vacation home
From $273 per night
(USD)
Contemporary Award Winning Hotel w\/Rooftop Close to Parks & Rollins College
1
1.0
2
Winter Park Florida Hotel
From $323 per night
(USD)
ADA Compliant Room - Contemporary Furnishings - Rooftop Pool - Close to Parks
1
1.0
2
Winter Park Florida Private vacation home
From $319 per night
(USD)
Private Balcony in Award Winning Hotel, Roof-top Pool, Close to Rollins College
1
1.0
2
Winter Park Florida Hotel
From $352 per night
(USD)
Award Winning Boutique Hotel Close to Parks & Rollins College, Rooftop Pool
1
1.0
4
Winter Park Florida Hotel
From $321 per night
(USD)
Private Balcony - Award Winning Accommodations w\/Rooftop Pool, Close to Parks!
1
1.0
4
Winter Park Florida Hotel
From $357 per night
(USD)
Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations
1
1.0
6
Winter Park Florida Private vacation home
From $357 per night
(USD)
Large Room Award Winning Hotel w\/Rooftop Pool - Close to Parks & Rollins College
1
1.0
2
Winter Park Florida Hotel
From $403 per night
(USD)
ADA Compliant Room in Award Winning Hotel w\/Rooftop Pool - Close to Parks!
1
1.0
6
Winter Park Florida Hotel
From $371 per night
(USD)
Coastal Feel - Modern Appeal
2
2.0
4
Winter Park Florida Private vacation home
From $158 per night
(USD)
Tiny Cottage - 3 MI to Downtwn w\/ Grill & Hammocks
1
1.0
2
Winter Park Florida Guest house
From $62 per night
(USD)
Temporary living that feels like home where you can relax and be yourself.
4
2.0
6
Maitland Florida Private vacation home
From $160 per night
(USD)
3 Bedroom Single_family 421262 by Houzlet
3
2.0
6
Orlando Florida Apartment
Click For Pricing
3 Bedroom Condo 418984 by Houzlet
3
3.0
6
Orlando Florida Condo
Click For Pricing
Casa Winter Park
4
4.0
8
Winter Park Florida Private vacation home
From $320 per night
(USD)
Orlando Vacation Rental < 2 Mi to Lake Ivanhoe!
2
1.0
4
Orlando Florida Cottage
From $69 per night
(USD)
Modern and Romantiv Villa
1
1.0
3
Winter Park Florida Guest house
From $77 per night
(USD)
17'coachman clipper tiny trailer
1
1.0
2
Orlando Florida Private vacation home
From $68 per night
(USD)
Charming Clean Home near East End Market - 40% Off Monthly Rate
3
2.0
6
Winter Park Florida Private vacation home
From $186 per night
(USD)
Comfy Home in Winter Park, can accommodate up 6 guests!
3
2.0
6
Winter Park Florida Private vacation home
From $228 per night
(USD)
A comfortable home close to the city, yet tucked away from the noise.
3
2.0
7
Orlando Florida Private vacation home
From $153 per night
(USD)
Casa Bella
5
4.0
8
Maitland Florida Private vacation home
From $320 per night
(USD)
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