Winter Park, Florida offers beautiful vacation homes in the greater Orlando area. The most common of these are fully equipped condos with decks, gardens, and all the amenities you could ask for. There are also lavish villas available, near the sea or within the city center. Another option for your upcoming vacation are expansive vacation homes with multiple bedrooms, bathrooms, and backyards.
Top 15 most Recommended Vacation Rentals in Winter Park
Discover your ideal Winter Park vacation rental with real-time comparisons of 171 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.
Vacation rentals with a balcony
Vacation Rentals With Fireplaces
Vacation rentals and apartments with air conditioning
Budget-friendly rental options
Enjoy affordable vacation rentals in Winter Park offering exceptional value for money
Top-Rated Vacation rentals in Winter Park
Book the highest-rated Winter Park vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money
Why choose HomeToGo?
Securely pay and stay your way
Choose local, trusted payment methods, plus trip insurance and add-on services.
Award-winning customer service
Experience seamless, hands-on support for any booking questions or concerns.
Verified reviews
Trust in the quality and comfort of your stay with verified guest reviews.
Price clarity, no surprises
Spend your budget exactly as planned by comparing thousands of providers.
Smart search made simple
Transform vacation planning into a joy with advanced, AI-powered search tools.
Find your dream stay
Explore 15 million+ rentals, the world’s biggest selection of vacation homes.
Popular Features & Amenities in Winter Park
Finding a rental with a pool is easy in Winter Park. One-third of the accommodations offer pools. Also, more House rental have pools than any other type of property. They are a great choice if you go in a group of 4, as that is the number of people they can accommodate on average. Among these vacation rentals, 77 of them are within 2 miles of water.
What are the best activities for families in Winter Park?
Tons of fun for families, too
Kids will love the Saturday Farmer's Market in Winter Park, where you can buy vegetables directly from growers, or eat some freshly-popped popcorn. Right on Orlando's doorstep, Winter Park is also within reach of Orlando's Airheads Trampoline Arena, as well as the world-famous DIsney World. Another popular destination for families is the Petting Farm at Green Meadows Farm.
What are the best places to discover the arts and culture of Winter Park ?
Winter Park: historic and interesting sites
The Charles Hosmer Morse Museum of American Art is full of timely pieces both classic and modern. To encounter art outdoors, check out the Albin Polasek Museum & Sculpture Gardens. Cornell Fine Arts Museum offers more sophisticated art to enjoy. If you want to be immersed in Winter Park's history and culture, stop by the Winter Park Historical Museum, Casa Feliz Historic Home Museum, and the Hannibal Square Heritage Center.
Information about vacation rentals in Winter Park
| 🏡 Vacation rentals available | 171 rentals |
|---|---|
| 🌙 Nightly prices starting at | $78 |
| ⭐ Popular amenities | Pool, Pets allowed and Internet |
| 🐾 Pet friendly homes | 81 homes |
| 🏊 Vacation rentals with pools | 52 homes |
Frequently Asked Questions
What is the average price per night for a vacation rental in Winter Park?
On average, vacation rentals in Winter Park cost around $78 per night. Nightly prices for house rentals are $253 on average. Apartment rentals in Winter Park cost on average $176 per night.
How many vacation rentals are available for booking in Winter Park?
Currently there are 171 vacation homes from 6 providers in Winter Park.
What are the most popular amenities for vacation rentals in Winter Park?
If you're looking to book a vacation rental in Winter Park, the most popular amenities are: Pets allowed, Pool and Internet.
How many vacation homes with pools are there in Winter Park?
Winter Park has 52 Hotel room and Apartment rental options on offer to rent.
Are pets allowed in vacation homes in Winter Park?
Finding a vacation rental in Winter Park that allows dogs is easy, with 81 pet-friendly available.
Top cities to visit
- Orlando
- St. Augustine
- Tampa
- Lake Placid
- Daytona Beach
- Kissimmee
- Cocoa Beach
- New Smyrna Beach
- Ocala
- Crystal River
- Vero Beach
- Palm Coast
- Ormond Beach
- Winter Garden
- Davenport
- Riverview
- Saint Augustine Beach
- Edgewater
- Flagler Beach
- Mount Dora
- Clermont
- Spring Hill
- The Villages
- Tarpon Springs
- Melbourne
- Winter Haven
- New Port Richey
- Leesburg
- Cape Canaveral
- Weeki Wachee
- Lake Mary
- Wesley Chapel
- Palm Bay
- Titusville
- Lake Buena Vista
- Sebring
- Daytona Beach Shores
- Brandon
- Crescent Beach
- Homosassa
- Merritt Island
- Melbourne Beach
- DeLand
- Pine Island
- Deltona
- Apopka
- Plant City
- Altamonte Springs
- Port Orange
- Lake Wales
Most Popular Destinations
- Vacation rentals in the Outer Banks (OBX)
- Cabin rentals in Gatlinburg, TN
- Cabin rentals in Hocking Hills, OH
- Cabin rentals in Broken Bow, OK
- Vacation rentals in Myrtle Beach
- Vacation rentals & cabins in Pigeon Forge
- Vacation rentals in Gulf Shores
- Vacation rentals in Vancouver
- Vacation rentals in Tybee Island
- Vacation rentals in Yellowstone
- Vacation rentals in Scottsdale
- Vacation rentals in Destin
- Vacation rentals & cabins near Lake Tahoe
- Vacation rentals in Panama City Beach
- Vacation rentals in North Myrtle Beach
- Vacation Rentals in Vancouver, WA
- Vacation rentals in Door County
- Vacation rentals & cabins in Branson
- Vacation rentals in Key West
- Vacation rentals in Cape Cod
- Vacation rentals & cabins in Yosemite
- Vacation rentals in Rosemary Beach
- Vacation rentals in Emerald Isle
- Cabin rentals in the Smoky Mountains, NC
- Vacation rentals in San Diego
- Vacation rentals in Miami
- Vacation rentals in Nashville
- Vacation rentals in Hilton Head Island
- Vacation rentals in Cape Coral
- Vacation rentals & cabins in Glacier National Park
- Vacation rentals & cabins in Estes Park
- Vacation rentals & cabins in the Great Smoky Mountains
- Vacation rentals in Las Vegas
- Vacation rentals in Siesta Key
- Vacation rentals in New Orleans
- Vacation rentals & cabins in Big Bear Lake
- Vacation rentals in Anna Maria Island
- Vacation rentals in Nashville
- Vacation rentals in Orange Beach
- Vacation rentals in New York City
- Vacation rentals in Oak Island
- Vacation rentals in Charleston
- Vacation rentals in Kauai
- Vacation rentals & cabins in Logan
- Vacation rentals in Virginia Beach
- Vacation rentals & cabins in Sedona
- Vacation rentals in Maui
- Vacation rentals & cabins in Zion National Park
- Vacation rentals & cabins in Colorado
- Vacation rentals in Florida
- Vacation rentals in Chicago
- Vacation rentals in Palm Springs
- Vacation rentals in Atlanta
- Vacation rentals in South Padre Island
- Vacation rentals in Breckenridge
- Vacation rentals in Cape May
- Vacation rentals in Lake Ozark
- Vacation rentals on Mackinac Island
- Vacation rentals in Colorado Springs