House vacation rentals in Winter Park

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Top-rated house rentals in Winter Park

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Guest favorite

Home in Winter Park

4.9 out of 5 average rating, 135 reviews

Guest Suite in Winter Park/Orlando

This private guest suite is next to our home but completely exclusive with a separate entrance, private bathroom and no access to the main house. The layout is like a studio apartment with a bedroom, dining area and kitchenette. Outside there is also a patio area for guests. Full Sail University- 1 mile University of Central Florida- 7 miles Orlando Int'l Airport - 11 miles Universal Studios- 18 miles Disney World- 23.8 miles Camping World Stadium- 10 miles Kia Center- 9 miles Downtown-8 miles

Jun 12 – 19

G$15,401 GYD per night

Guest favorite

Home in Winter Park

4.92 out of 5 average rating, 105 reviews

A Rare Jewel in the heart of Winter park. Can walk

This lovely 3 bedrooms, 2 bath house is located in the most desirable area of Winter Park. Only few steps from Park Ave. You can walk to all the restaurants, Wine room, coffee shops, stores, art galleries, Museum, Park, Rollins College, Winter Park Community Center. Its only 25 minutes drive to the airport, 45 minutes to the beach, and close to family-friendly activities, nightlife, public transport. This house is great for families, couples, solo adventurers, business travelers, and big groups.

Sep 16 – 23

G$85,386 GYD per night

Guest favorite

Home in Orlando

4.97 out of 5 average rating, 124 reviews

Walk Everywhere! Lake Eola DTO Thornton Park

Located on a brick paved road in the heart of beautiful, historic Thornton Park in Downtown Orlando with restaurants, coffee shops, and bars just steps from your front door! Walk to Kia (Amway) Center, Phillips Center, Exploria Stadium, Central Business District, Church St Station, Publix, bars, restaurants, & lakes! Close to I-4 & freeways! 7 miles to Universal, International Drive, outlet malls, & springs! 16 miles to Disney Parks & Disney Springs! 50 miles to Daytona & Cocoa Beaches!

Dec 17 – 24

G$29,902 GYD per night

Guest favorite

Home in Altamonte Springs

4.97 out of 5 average rating, 276 reviews

Eclectic Home Where Luxury Meets Affordability

Welcome to the Haven at Temper Wild - Your home away from home. We offer fully free amenities, luxury bedding and pillows, and quintessential design throughout the rooms and home. There are work spaces in every bedroom, ultra-fast wifi, games galore, and a beautiful outdoor space equipped with outdoor dining and lounging. Pet Fee's per pet: $100 (You must notify host if you are bringing a pet prior to booking) Read the rules of the property before booking, to ensure that you are OK with them.

Sep 13 – 20

G$37,231 GYD per night

Guest favorite

Home in Orlando

4.93 out of 5 average rating, 151 reviews

Cozy Downtown Orlando House

Your home away from home. Close to Downtown Orlando and just minutes to all the major theme parks. Private entrance with keypad entry. Private patio with seating. Full kitchen. Private Washer/Dryer. Great access to many local bars, restaurants, and entertainment within walking distance and many more a short drive away. Disney, Universal, Orlando International Airport, Orange County Convention Center are all within a half-hour drive. Only an hour from the beach, Kennedy Space Ctr., etc.

Aug 8 – 15

G$25,573 GYD per night

Guest favorite

Home in Winter Garden

4.92 out of 5 average rating, 167 reviews

Cozy Winter Garden Home 20 MINUTES FROM DISNEY

Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.

Apr 20 – 27

G$25,770 GYD per night

Guest favorite

Home in Winter Park

4.94 out of 5 average rating, 111 reviews

Modern, Quiet & Cozy - Entire house /Winter park

Embrace Tranquil Living in Winter Park, Florida. Located in a quiet neighborhood NE of downtown this recently renovated house is modern, clean, and cozy. Short drive to other great attractions in Orlando. Its central location is minutes away from Park Ave, the University of Central Florida, Rollins College, Full Sail University, Downtown Orlando, MCO Airport, Amway Center, Dr. Phillips, Science Center, Orlando City Stadium, and much more! You need to be at least 18 years old to book.

Oct 20 – 27

G$33,210 GYD per night

Guest favorite

Home in Oviedo

4.96 out of 5 average rating, 227 reviews

Cute cottage near UCF & trails. No cleaning fee

Our cottage is nestled behind Oviedo’s oldest home. The cottage boasts lots of windows with a beautiful view of the outdoors. Inside the cottage is a queen-size bed, table for 2-4, kitchenette with refrigerator, toaster and microwave, TV with Netflix and Prime, plus WiFi. There is a tall claw foot tub which can be difficult for people with mobility issues. The cottage is connected to the main house but has its own entrance and guests have complete privacy. There are no shared spaces.

Sep 30 – Oct 7

G$23,232 GYD per night

Guest favorite

Home in Maitland

4.97 out of 5 average rating, 117 reviews

The Butterfly Bungalow near Park Ave

This 1950s bungalow has been lovingly restored to maintain it's Florida charm and offer simple comforts. Located in a family-friendly neighborhood just a few blocks from the Enzian Theater, the bungalow is close to restaurants and shops lining the cobblestone streets of Park Ave, and centrally located to historic areas of both Winter Park and Maitland. Park Ave shopping district - 1.5 miles Whole Foods - 0.8 miles Publix - 0.8 miles SunRail - 1.7 miles Downtown Orlando - 8 miles

Sep 10 – 17

G$27,995 GYD per night

Guest favorite

Home in Orlando

4.95 out of 5 average rating, 100 reviews

Trendy Downtown Orlando Oasis

Updated three-bedroom home, only minutes from I-4, which means easy access to your favorite spots in and around Orlando. - Winter Park Village: 5 minutes - Downtown Orlando: 10 minutes - Amway Center and Camping World Stadium: 10 minutes - Disney World, Universal Studios, and I-Drive: 20 minutes Perfect for groups or families. Plenty of free parking in driveway and curb side. No parties or events please. Orlando Permit #: STR – 1094537.

May 9 – 16

G$40,400 GYD per night

Guest favorite

Home in Orlando

4.93 out of 5 average rating, 120 reviews

Hidden Gem in SODO! - MCO ~16min

Enjoy your stay in this cozy & comfy 1 bedroom and bath house located in the desirable South Downtown Orlando. Rest well in the large queen size bed, with a 65 inch smart TV, equipped with Netflix. Restaurants and stores in walking distance. Wifi & parking are included MCO Airport: ~16 Min Drive Disney: ~20 Min Drive Universal Studios: ~15 Min Drive Hollywood Studios: ~20 Min Drive Sea World: ~15 Min Drive Downtown Orlando: ~5 Min Drive

Apr 16 – 23

G$20,192 GYD per night

Guest favorite

Home in Winter Park

4.87 out of 5 average rating, 104 reviews

Comfy 3 Bedrooms - 2 Bathrooms home with pool.

Nice home, with pool and spacious backyard, located in quiet neighborhood with small park for kids. Attractions: Located 30 minutes from Universal Studios, 40 minutes from Disney World and an hour to either Daytona or Cocoa Beach. Universities: 15 minutes or less to Full Sail, UCF, Valencia and Rollins College. **DISCLAIMER- No lifeguard on duty, enter the pool at your own risk**

Sep 4 – 11

G$43,268 GYD per night