A two-story house with a balcony, surrounded by lush greenery and trees.

Winter Park Holiday Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Winter Park holiday rentals

3 bedrooms, Internet

Walk to Epic Universe and Occc From This Condo

Walk to Epic Universe and Occc From This Condo
2.0 star property
Orlando
The price is S$502
includes taxes & fees
21 Jul - 22 Jul
Walk to Epic Universe and Occc From This Condo
Living area

The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is S$290
includes taxes & fees
28 Jul - 29 Jul
The Blue Aztec
Living area

Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
The price is S$198
includes taxes & fees
23 Jul - 24 Jul
Boho Nights
2 bedrooms, desk, free WiFi

The Front Porch

The Front Porch
3.0 star property
Downtown Sanford
9.2 out of 10, Wonderful, (5 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The price is S$287
includes taxes & fees
9 Jul - 10 Jul
The Front Porch
Interior

Totally 80's

Totally 80's
3.0 star property
Sanford
8.4 out of 10, Very good, (10 reviews)
"Great location to downtown Sanford!"
United States
Kathleen
The price is S$178
includes taxes & fees
12 Jul - 13 Jul
Totally 80's
Lobby

Pinnacle Apartments W Amenties by Heavenly Homes

Pinnacle Apartments W Amenties by Heavenly Homes
4.0 star property
Orlando
The price is S$450
includes taxes & fees
14 Jul - 15 Jul
Pinnacle Apartments W Amenties by Heavenly Homes
Interior

Upstay Golfer's Retreat w Patio at Ventura Resort

Upstay Golfer's Retreat w Patio at Ventura Resort
3.0 star property
Ventura
The price is S$313
includes taxes & fees
15 Jul - 16 Jul
Upstay Golfer's Retreat w Patio at Ventura Resort
Exterior

The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, Excellent, (9 reviews)
"Location, location, location!!! What a cute and fun space. I thoroughly enjoyed my entire Jazz Loft experience. Look fwd to next trip! "
United States
Deborah
The price is S$185
includes taxes & fees
9 Jul - 10 Jul
The Jazz Loft
Interior

Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.6 out of 10, Exceptional, (18 reviews)
"Great location for restaurants and river trail. Very well stocked so it is an easy and comfortable stay."
United States
Nancy
The price is S$194
includes taxes & fees
21 Jul - 22 Jul
Bella Breeze
Free WiFi

Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is S$206
includes taxes & fees
9 Jul - 10 Jul
Cozy Modern Studio
3 bedrooms, Internet

Lrg Condo w Scenic Patio Views - Next to Occc

Lrg Condo w Scenic Patio Views - Next to Occc
2.0 star property
Orlando
The price is S$489
includes taxes & fees
12 Jul - 13 Jul
Lrg Condo w Scenic Patio Views - Next to Occc
6 outdoor pools, free pool cabanas, pool umbrellas

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
Orlando
9.2 out of 10, Wonderful, (6,040 reviews)
"Have stayed there before. Great location for families with a pool for each area of the resort."
United States
Debra
The price is S$216
includes taxes & fees
6 Aug - 7 Aug
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Living area

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
4.0 star property
Kirkman North
The price is S$379
includes taxes & fees
13 Jul - 14 Jul
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
2 outdoor pools, open 7:00 AM to 11:00 PM, free pool cabanas

Magical Moment Vacation Condos

Magical Moment Vacation Condos
4.0 star property
International Drive District
10.0 out of 10, Exceptional, (1 review)
"Very Clean room staff were great !! Definitely would stay again !"
United States
stephanie
The price is S$459
includes taxes & fees
12 Jul - 13 Jul
Magical Moment Vacation Condos
Exterior

The Contemporary

The Contemporary
3.0 star property
Downtown Sanford
The price is S$350
includes taxes & fees
14 Jul - 15 Jul
The Contemporary
2 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas, pool loungers

Villas at Fortune Place

Villas at Fortune Place
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (173 reviews)
"I've stayed here before and it is very good for the price you get! Staff was lovely and the room was amazing."
United States
Jarelieze
The price is S$133
includes taxes & fees
9 Jul - 10 Jul
Villas at Fortune Place
Interior

Upstay: Family-friendly Getaway With Spa & Pool

Upstay: Family-friendly Getaway With Spa & Pool
3.5 star property
Orlando
10.0 out of 10, Exceptional, (1 review)
"Clean room"
United States
Yves marie
The price is S$352
includes taxes & fees
12 Jul - 13 Jul
Upstay: Family-friendly Getaway With Spa & Pool
Private kitchen

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
4.0 star property
Downtown Orlando
The price is S$544
includes taxes & fees
20 Jul - 21 Jul
Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
Living area

Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning

Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
3.5 star property
Colonialtown South
The price is S$507
includes taxes & fees
14 Jul - 15 Jul
Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
Interior

Riviere 3BR Apartment Stylish King Family Pets Friendly Pool & Gym Near Epic UniverseOpens

Riviere 3BR Apartment Stylish King Family Pets Friendly Pool & Gym Near Epic UniverseOpens
4.0 star property
International Drive District
The price is S$481
includes taxes & fees
15 Jul - 16 Jul
Riviere 3BR Apartment Stylish King Family Pets Friendly Pool & Gym Near Epic UniverseOpens
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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"."
Daigrid 2-night trip
Posted 2 hours ago
Universal's Cabana Bay Beach Resort

Frequently asked questions

Can I find holiday rentals in Winter Park?

Yes, there are holiday rentals in Winter Park close to Kraft Azalea Gardens, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Winter Park. Make sure you have time to check out the university setting and gardens during your trip.

How many holiday rentals are there in Winter Park?

Expedia has 53 holiday rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Albin Polasek Museum and Sculpture Gardens and Morse Museum of American Art, whereas Lake Virginia and Kraft Azalea Gardens are a couple of picturesque spots to enjoy the outdoors. Kia Center and Universal Studios Florida are other popular places to visit in the area.

What are holiday rentals like in Winter Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Park. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for families.