Winter Park Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Winter Park

2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas
Lake Buena Vista Resort Village & Spa
4.0 star property
8.4 out of 10, Very good, (7263)
"Shower water was not warm"
The price is CA $240
CA $306 total
includes taxes & fees
Jun 2 - Jun 3
Lake Buena Vista Resort Village & Spa
Outdoor pool, pool umbrellas, sun loungers
Avanti International Resort
3.0 star property
7.8 out of 10, Good, (2114)
"Was a pleasure my stay at Avanti, close to everything, the most clean hotel that I stayed in Orlando so far. And the smell at the reception it’s wonderful ! Good job guys 👏👏👏👏👏"
The price is CA $120
CA $159 total
includes taxes & fees
Jun 6 - Jun 7
Avanti International Resort
Meeting facility
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, (4866)
"The location is the reason for the stay and was priceless to have the opportunity to stay there on a layover. "
The price is CA $272
CA $306 total
includes taxes & fees
Jun 1 - Jun 2
Hyatt Regency Orlando International Airport
Save an average of 15% on thousands of hotels when you're signed in
Outdoor pool, a heated pool, pool umbrellas, sun loungers
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
3.5 star property
8.6 out of 10, Excellent, (3151)
"Three night stay was great! No complaints. Hotel staff was friendly and accommodating. Great location. The pool and poolside bar are open till 11 which was our favorite. The on-site restaurant was open late. There is a small store and arcade as well. "
The price is CA $115
CA $170 total
includes taxes & fees
May 30 - May 31
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
Water park
CoCo Key Hotel and Water Resort 
3.5 star property
7.4 out of 10, Good, (3771)
"The place is really great for family and children, staff friendly and polity, great pool and water activities. Food very convenient and inexpensive. All that being said, public bathrooms need to be continuously monitored and cleaned. I have to give two stars in this area. Everything else, exceptional, "
The price is CA $139
CA $222 total
includes taxes & fees
Jun 10 - Jun 11
CoCo Key Hotel and Water Resort 
2 outdoor pools, a heated pool, pool umbrellas, sun loungers
Floridays Resort Orlando
3.5 star property
8.6 out of 10, Excellent, (10693)
"Excellent property "
The price is CA $202
CA $273 total
includes taxes & fees
Jun 10 - Jun 11
Floridays Resort Orlando
Terrace/patio
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
3.0 star property
7.0 out of 10, Good, (2442)
"Amazing stay and service "
The price is CA $166
CA $187 total
includes taxes & fees
May 30 - May 31
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Lobby
Embassy Suites by Hilton Orlando International Dr ICON Park
3.5 star property
8.6 out of 10, Excellent, (1508)
"Love the full breakfast options and the free drinks during the evening reception! All the staff i encountered was super nice and helpful "
The price is CA $173
CA $194 total
includes taxes & fees
Jun 6 - Jun 7
Embassy Suites by Hilton Orlando International Dr ICON Park
Property entrance
The View Studio Suites and Event Venue
3.5 star property
8.6 out of 10, Excellent, (204)
"Spacious place, quiet and a huge parking. Stayed with the family and it was convenient. Should invest in an ice machine per floor and improve breakfast."
The price is CA $96
CA $107 total
includes taxes & fees
May 30 - May 31
The View Studio Suites and Event Venue
Terrace/patio
Holiday Inn & Suites Across From Universal Orlando, an IHG Hotel
3.0 star property
7.2 out of 10, Good, (571)
"All staff were friendly. Air conditioning was poor making hotel and room very warm."
The price is CA $119
CA $163 total
includes taxes & fees
Jun 6 - Jun 7
Holiday Inn & Suites Across From Universal Orlando, an IHG Hotel
Pillowtop beds, in-room safe, desk, blackout drapes
Wingate by Wyndham - Orlando International Airport
3.0 star property
8.8 out of 10, Excellent, (4000)
"Was a quick trip and had an early flight so being close to airport was convenient "
The price is CA $111
CA $124 total
includes taxes & fees
May 30 - May 31
Wingate by Wyndham - Orlando International Airport
Indoor pool, outdoor pool, pool umbrellas
Embassy Suites by Hilton Orlando International Dr Conv Ctr
3.5 star property
8.6 out of 10, Excellent, (1336)
"Nice and clean , great area, very happy with the service and all the hotel offer, the only negative is that they charge for parking, I was not aware until checkout."
The price is CA $178
CA $200 total
includes taxes & fees
Jun 9 - Jun 10
Embassy Suites by Hilton Orlando International Dr Conv Ctr
2 restaurants, lunch, dinner served; American cuisine
Embassy Suites by Hilton Orlando Lake Buena Vista South
3.5 star property
9.2 out of 10, Wonderful, (1714)
"Great Location and quiet "
The price is CA $196
CA $222 total
includes taxes & fees
Jun 16 - Jun 17
Embassy Suites by Hilton Orlando Lake Buena Vista South
Outdoor pool
The Point Hotel & Suites
3.5 star property
8.0 out of 10, Very good, (2959)
"Great Place in a great location. Great Staff that help with any needs in a timely manner"
The price is CA $127
CA $159 total
includes taxes & fees
May 30 - May 31
The Point Hotel & Suites
Reception
Florida Hotel & Conference Center in the Florida Mall
3.5 star property
9.0 out of 10, Wonderful, (1464)
"I have stay here many times, always pleasant."
The price is CA $196
CA $252 total
includes taxes & fees
Jun 9 - Jun 10
Florida Hotel & Conference Center in the Florida Mall
Presidential Suite, 1 King Bed, Non Smoking | View from room
Embassy Suites by Hilton Orlando Downtown
3.5 star property
8.8 out of 10, Excellent, (1363)
"Exceptional service, very attentive. "
The price is CA $231
CA $259 total
includes taxes & fees
Jun 10 - Jun 11
Embassy Suites by Hilton Orlando Downtown
Outdoor pool, pool umbrellas, sun loungers
Sonder at The Point
4.0 star property
8.4 out of 10, Very good, (493)
"Excellent experience, nice place ! "
The price is CA $316
CA $356 total
includes taxes & fees
May 30 - May 31
Sonder at The Point
The Club House
Orlando Lakefront Tiny House Community
4.5 star property
9.2 out of 10, Wonderful, (144)
"If you love Tiny Homes!!! This is the place. Management is phenomenal. Great communication and helpful. We stayed in The View. Loved it. Big window facing the Lake. Peaceful Cant wait to go BACK!!"
The price is CA $104
CA $217 total
includes taxes & fees
Jun 4 - Jun 5
Orlando Lakefront Tiny House Community
Outdoor pool, open 8:00 AM to 10:00 PM, sun loungers
Hilton Garden Inn Orlando at SeaWorld
3.0 star property
8.6 out of 10, Excellent, (1213)
"Staff is friendly and helpful "
The price is CA $124
CA $140 total
includes taxes & fees
May 30 - May 31
Hilton Garden Inn Orlando at SeaWorld
Bar (on property)
Holiday Inn Express & Suites S Lake Buena Vista, an IHG Hotel
2.5 star property
8.6 out of 10, Excellent, (859)
"wonderful experience "
The price is CA $134
CA $188 total
includes taxes & fees
Jun 4 - Jun 5
Holiday Inn Express & Suites S Lake Buena Vista, an IHG Hotel
Don't see what you're looking for?
See all available properties in Winter Park
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.

Winter Park Vacation Rental Travel Info

Number of vacation rentals
75
Popular accommodation
Winter Park private vacation homes
Known landmarks
Orlando Science Center, Church Street Station and Orlando Museum of Art
International airport
Orlando, FL (MCO-Orlando Intl.)

Other types of properties in Winter Park you may be interested in

Front of property - evening/night
DoubleTree by Hilton Hotel Orlando at SeaWorld
4.0 star property
7.0 out of 10, Good, (8809)
"Property was nice but the customer service was the best part diego at the front desk was an amazing help and so was everyone else the parking was a lottle bit of a headache there was nothing available and it was 30$ a night but when i talked to them at the front desk they waived the fee thats why i say if nothing else was to being me back the customer service aspect would "
The price is CA $115
CA $168 total
includes taxes & fees
Jun 6 - Jun 7
DoubleTree by Hilton Hotel Orlando at SeaWorld
Outdoor pool
DoubleTree by Hilton at the Entrance to Universal Orlando
4.0 star property
8.4 out of 10, Very good, (6314)
"I like that you can walk to Universal. The staff were friendly. The room was clean."
The price is CA $149
CA $167 total
includes taxes & fees
May 30 - May 31
DoubleTree by Hilton at the Entrance to Universal Orlando
Exterior
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
3.5 star property
6.4 out of 10, (5469)
"The oasis pool borders inside was dirty and the white towels in the water park are to old and small the rest of the facilities are fine "
The price is CA $115
CA $197 total
includes taxes & fees
Jun 10 - Jun 11
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winter Park. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Winter Park?

Yes, we offer vacation rentals in Winter Park close to Kraft Azalea Gardens, or you can choose 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.

What's the top vacation rental that Winter Park has to offer?

Marriott's Sabal Palms: Visitors like this Winter Park vacation home rental. It is located near the airport and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a spa tub.

How many vacation rentals are there in Winter Park?

Expedia has 75 vacation rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Casa Feliz Historic Home Museum and Albin Polasek Museum and Sculpture Gardens, whereas Kraft Azalea Gardens and Alfond Swimming Pool are a couple of picturesque spots to enjoy the outdoors. Universal Studios Florida and Universal Orlando Resort are other popular places to visit in the area.

What are vacation rentals like in Winter Park?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Winter Park. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a small group gathering.

Recent reviews of Winter Park properties
Expedia verified reviews