Search Vacation Homes in Winter Park

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Nov 21 - Nov 23
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Dec 12 - Dec 14
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Jan 9 - Jan 11

Vacation Homes in Winter Park

Pool
Magic Studio

Magic Studio

Orlando
9.4 out of 10, Exceptional, (3)
"The finishes were nice and it was clean. The mini-split won’t keep the room cool enough. We didn’t notice until the next day that the ceiling light is also a fan. It definitely helped keep the room cooler. Parking is on the street. We were really only in the room to sleep so it sufficed. "
United States
Kristie B.
$148 nightly
The price is $164
Nov 17 - Nov 18
Total with taxes and fees
Magic Studio
Fridge, microwave, oven, stovetop
Sleek, Spacious & Central – Your Ideal Getaway

Sleek, Spacious & Central – Your Ideal Getaway

2.0 star property
Fairview Shores
$172 nightly
The price is $191
Nov 11 - Nov 12
Total with taxes and fees
Sleek, Spacious & Central – Your Ideal Getaway
Private kitchen
5-bedroom,6bed house in superb Winter Park

5-bedroom,6bed house in superb Winter Park

Winter Park
$248 nightly
The price is $275
Nov 16 - Nov 17
Total with taxes and fees
5-bedroom,6bed house in superb Winter Park
Terrace/patio
Winter Park Gem, 2BR Near Parks, 3MI to Downtown

Winter Park Gem, 2BR Near Parks, 3MI to Downtown

College Park
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay — the house was spotless, comfortable, and offered plenty of space. The peaceful neighborhood and convenient location made it easy to explore the area."
United States
Danielle H.
$246 nightly
The price is $273
Nov 11 - Nov 12
Total with taxes and fees
Winter Park Gem, 2BR Near Parks, 3MI to Downtown
Private kitchen
Mills House @WP. Sleeps 11 Renovated. Queen beds

Mills House @WP. Sleeps 11 Renovated. Queen beds

Fairview Shores
$2,317 nightly
The price is $2,579
Nov 13 - Nov 14
Total with taxes and fees
Mills House @WP. Sleeps 11 Renovated. Queen beds
Fridge, microwave, oven, stovetop
Home Sweet Home

Home Sweet Home

Sanford
9.6 out of 10, Exceptional, (21)
"It was a great location for our trip and everything was true to the listing. The host was very responsive and helpful."
United States
K B.
$260 nightly
The price is $288
Nov 11 - Nov 12
Total with taxes and fees
Home Sweet Home
TV
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

2.0 star property
Apopka
10.0 out of 10, Exceptional, (1)
"We had such a lovely stay at the quaint and charming mother-in-law suite in Apopka, FL. The space was spotless and cozy—perfect for a romantic getaway. We especially loved the serene garden setting with a pool and jacuzzi. Its location was ideal too: just minutes from the highway for easy trips into Orlando, or a scenic drive up 441 to explore the delightful shops and restaurants of Mount Dora. A peaceful retreat with the best of Central Florida within reach."
United States
Carlos J
$93 nightly
The price is $102
Nov 12 - Nov 13
Total with taxes and fees
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Terrace/patio
Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!

Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!

Buena Ventura Lakes
10.0 out of 10, Exceptional, (21)
"The view is beautiful and peaceful. The neighborhood is quiet.Sleep number bed! Dish soap! Every need is anticipated.Loved our stay!"
United States
Judah G.
$300 nightly
The price is $335
Nov 11 - Nov 12
Total with taxes and fees
Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
Interior
Charming 2-bedroom apartment in house with AC, WiFi included

Charming 2-bedroom apartment in house with AC, WiFi included

Apopka
10.0 out of 10, Exceptional, (9)
"Perfect little spot for a family of 3 to stay. We spent most days exploring local natural springs and would stay at night for dinner and sleep. The place was very clean and had everything we needed for our stay. It felt very secure and safe as it is inside a gated community. "
United States
Elvis R.
$134 nightly
The price is $148
Nov 11 - Nov 12
Total with taxes and fees
Charming 2-bedroom apartment in house with AC, WiFi included
Exterior
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

Deltona
9.6 out of 10, Exceptional, (10)
"The space was private, comfortable and very clean. Ashlee is an amazing hostess. "
United States
Belinda M.
$128 nightly
The price is $142
Nov 11 - Nov 12
Total with taxes and fees
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Fridge, microwave, oven, stovetop
Full House with Big Fenced Backyard, Washer & Dryer and Pet-Friendly.

Full House with Big Fenced Backyard, Washer & Dryer and Pet-Friendly.

2.0 star property
Clear Lake
9.6 out of 10, Exceptional, (5)
"We had a lovely stay here, would definitely recommend! Thanks!"
United States
Jamie K.
$219 nightly
The price is $243
Nov 11 - Nov 12
Total with taxes and fees
Full House with Big Fenced Backyard, Washer & Dryer and Pet-Friendly.
Fridge, microwave, oven, stovetop
Charming 3-bedroom home away from home.

Charming 3-bedroom home away from home.

Chuluota
9.8 out of 10, Exceptional, (19)
"Perfect stay while visiting local family. "
United States
Kerri W.
$337 nightly
The price is $373
Nov 11 - Nov 12
Total with taxes and fees
Charming 3-bedroom home away from home.
Interior
Comfortable 1 bedroom home

Comfortable 1 bedroom home

Azalea Park
8.8 out of 10, Excellent, (3)
"Host and location were awesome . Nestled in an great neighborhood. Will definitely stay again."
United States
Ventrell J.
$175 nightly
The price is $175
Nov 11 - Nov 12
Total with taxes and fees
Comfortable 1 bedroom home
Exterior
“The Clementine” Boho Home in Orlando’s Food Scene

“The Clementine” Boho Home in Orlando’s Food Scene

Park Lake - Highland
9.8 out of 10, Exceptional, (16)
"Great"
United States
Hank
$164 nightly
The price is $182
Nov 11 - Nov 12
Total with taxes and fees
“The Clementine” Boho Home in Orlando’s Food Scene
Outdoor pool, a heated pool
Luxury 5 BR at Disney Universal free heated pool high chair stroller playpen

Luxury 5 BR at Disney Universal free heated pool high chair stroller playpen

Kissimmee
10.0 out of 10, Exceptional, (43)
"We enjoyed our stay! The condo was very nice & clean. The location was very convenient too. Our only complaint would have been more towels and a patio table set because we love to dine outside! We would definitely book again. Thanks again."
United States
Celeste P.
Luxury 5 BR at Disney Universal free heated pool high chair stroller playpen
1 bedroom, iron/ironing board, free WiFi, bed sheets
The Cozy Crash Pad: Tiny House Experience

The Cozy Crash Pad: Tiny House Experience

Orlando
9.2 out of 10, Wonderful, (21)
"It was incredible! The tiny home feels incredibly cozy and was super easy to find. We had a wonderful visit."
United States
Tristen H.
$134 nightly
The price is $148
Nov 23 - Nov 24
Total with taxes and fees
The Cozy Crash Pad: Tiny House Experience
Dining
Florida Vacation with pool fun for families

Florida Vacation with pool fun for families

Casselberry
9.6 out of 10, Exceptional, (37)
"Great communication. Convenient, central location. Exactly as described!"
United States
Stacie J.
$303 nightly
The price is $335
Dec 1 - Dec 2
Total with taxes and fees
Florida Vacation with pool fun for families
Fridge, microwave, oven, stovetop
Renovated Peaceful Luxury Walk to Mall Park Publix

Renovated Peaceful Luxury Walk to Mall Park Publix

Altamonte Springs
9.4 out of 10, Exceptional, (12)
"We really enjoyed our time here. The porch was really nice to sit out on and it was in a perfect location. Super bathroom and tv size is massive!!"
United States
Amy A.
$171 nightly
The price is $189
Nov 11 - Nov 12
Total with taxes and fees
Renovated Peaceful Luxury Walk to Mall Park Publix
Living area
Kissimmee resort home with pool

Kissimmee resort home with pool

Kissimmee
9.4 out of 10, Exceptional, (16)
"Great communication, area and stay."
United States
Jennifer C.
$410 nightly
The price is $459
Nov 11 - Nov 12
Total with taxes and fees
Kissimmee resort home with pool
Pool
Cozy Golf Condo | 3 Pools, Gym, 15min to Airport

Cozy Golf Condo | 3 Pools, Gym, 15min to Airport

Ventura
9.0 out of 10, Wonderful, (2)
"We couldn’t ask for a better place to stay and can’t wait for our next trip. The location is beautiful and peaceful, the condo was immaculate and the host(s) were accommodating, reachable and took the time to reply whenever we had questions. Thank you! "
United States
Susan O.
$185 nightly
The price is $185
Nov 11 - Nov 12
Total with taxes and fees
Cozy Golf Condo | 3 Pools, Gym, 15min to Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Park Hotel Reviews

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"GREAT "
Joseph 1-night trip
Posted 12 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Find out more about Winter Park

Winter Park Vacation Homes information

Number of reviews
232
Accommodation
6017 Vacation Homes
Lowest Price
$102
Highest Price
$2,579

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