Compare Winter Park Vacation Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Winter Park Rentals

Wellborn Hotel Downtown, Sonder by Marriott Bonvoy

Free Cancellation

Reserve now, pay when you stay

4.96 mi from city center

Guests staying at Wellborn Hotel Downtown, Sonder by Marriott Bonvoy enjoy free WiFi in public areas and a terrace. If you drive, put free parking to good use.

Parking included

Free WiFi

10.56 mi from city center

Guests staying at Century Millenia enjoy an outdoor pool, free WiFi in public areas, and a garden. There's free parking if you drive. Staff members can answer questions about accommodations, and also provide concierge services.

Pool

Washer

Florida Hotel & Conference Center in the Florida Mall

Free Cancellation

Reserve now, pay when you stay

11.23 mi from city center

At Florida Hotel & Conference Center in the Florida Mall, guests enjoy an outdoor pool, a gym, and free WiFi in public areas. There's RV, bus, and truck parking and a free theme park shuttle. The front desk has multilingual staff on hand 24/7 to help with securing valuables, luggage storage, and tours or tickets. Other amenities at this family-friendly aparthotel include a hot tub, a conference center, and a 24-hour business center.

Pool

Hot Tub

Free Cancellation

Reserve now, pay when you stay

12.42 mi from city center

Guests staying at The Point Hotel & Suites enjoy an outdoor pool, a gym, and free WiFi in public areas. If you drive, take advantage of free parking. Front-desk staff can answer questions 24/7, and assist with dry cleaning/laundry, securing valuables, and luggage storage. Additional amenities include a hot tub, a computer station, and express check-out.

Pool

Hot Tub

Free Cancellation

Reserve now, pay when you stay

12.57 mi from city center

Guests staying at The View Studio Suites and Event Venue enjoy a 24-hour gym, free WiFi in public areas, and a picnic area. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready.

Breakfast included

Pet friendly

Free Cancellation

Reserve now, pay when you stay

12.88 mi from city center

At staySky Suites - I Drive Orlando, guests enjoy an outdoor pool, a 24-hour gym, and free WiFi in public areas. You can take advantage of free parking, along with a theme park shuttle. Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, securing valuables, and tours or tickets. Other amenities at this family-friendly aparthotel include a hot tub, a business center, and a meeting room.

Pool

Hot Tub

Free Cancellation

Reserve now, pay when you stay

15.78 mi from city center

Parc Corniche Condominium Suite Hotel features an outdoor pool, a children's pool, and a gym. There's free parking and a free theme park shuttle. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, securing valuables, and dry cleaning/laundry. Other amenities at this family-friendly aparthotel include a hot tub, a 24-hour business center, and coffee/tea in a common area.

Pool

Hot Tub

Free Cancellation

Reserve now, pay when you stay

17 mi from city center

Guests of Floridays Resort Orlando have access to 2 outdoor pools, a gym, and conference space. You can take advantage of free parking, along with an area shuttle. Multilingual staff at the front desk are standing by 24/7 to help with tours or tickets, dry cleaning/laundry, and luggage storage. Other amenities at this family-friendly condominium resort include a 24-hour business center, a computer station, and an arcade/game room.

Pool

Kitchen

17.64 mi from city center

At Blue Tree Resort at Lake Buena Vista, guests enjoy 4 outdoor pools, a children's pool, and a gym. Transportation is made easy with a free theme park shuttle. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, luggage storage, and securing valuables. Other amenities at this family-friendly aparthotel include 2 hot tubs, free WiFi in public areas, and an outdoor tennis court.

Pool

Hot Tub

18.77 mi from city center

Blue Heron Beach Resort features 2 outdoor pools, a children's pool, and a gym. Free parking is included with your stay. A multilingual staff is on hand to assist with concierge services, securing valuables, and luggage storage. Other amenities at this family-friendly aparthotel include free WiFi in public areas, a hot tub, and an arcade/game room.

Pool

Hot Tub

19.34 mi from city center

Guests of Lake Buena Vista Resort Village & Spa have access to a full-service spa, 2 outdoor pools, and a children's pool. There's free parking and a free theme park shuttle. Multilingual staff at the front desk are standing by 24/7 to help with tours or tickets, securing valuables, and luggage storage. Other amenities at this spa condominium resort include a 24-hour gym, 3 hot tubs, and a steam room.

Pool

Hot Tub

Free Cancellation

Reserve now, pay when you stay

20.04 mi from city center

Guests of WorldQuest Orlando Resort have access to an outdoor pool, a 24-hour gym, and free WiFi in public areas. You can take advantage of free parking, along with a free theme park shuttle. The front desk has multilingual staff on hand 24/7 to help with concierge services, securing valuables, and dry cleaning/laundry. Other amenities at this family-friendly aparthotel include a business center, coffee/tea in a common area, and a computer station.

Pool

Kitchen

Don't see what you're looking for?

See all available properties in Winter Park

View all properties

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 Large Group Rentals

Quiet Oasis in Lovely Neighborhood

Orlando

9.6/10 Exceptional! (138 reviews)

Marriott's Sabal Palms

8805 World Center Dr, Orlando, FL

9.4/10 Exceptional! (192 reviews)

Vista Cay Resort by Casiola Vacation Homes

4874 Cayview Ave, Orlando, FL

8.6/10 Excellent! (180 reviews)

Blocks a way to Universal Studios. Full Single Family with pool, and amenities.

Orlando

8/10 Very Good! (6 reviews)

Beautiful 9 bedroom home with pool! Minutes away from theme parks.

Kissimmee

5.2/10 (28 reviews)

Marriott's Imperial Palm Villas

8404 Vacation Way, Orlando, FL

How to Book Vacation Rentals in Winter Park

🏠 What is the best price for Winter Park vacation rentals?

Winter Park vacation rentals range in price, starting at per night.

🏠 What types of vacation rentals in Winter Park can I rent?

Orbitz offers a wide range of Winter Park rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Winter Park condo rentals.

🏠 Is it free to cancel my Winter Park vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.

🏠 How do I find the best deals to rent a Winter Park vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Winter Park. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.

🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.

🏠 What are the advantages of booking a vacation rental in Winter Park?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Winter Park apartments and enjoy an extended stay.

🏠 Why should I book my vacation rental with Orbitz in Winter Park?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Winter Park package deals will get you even more savings.