
Condo holiday rentals in Winter Park
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Top-rated condo rentals in Winter Park
Guests agree: These condos are highly rated for location, cleanliness and more.

Private Rooftop Suite! The best of the best
Enjoy a stylish experience at this centrally-located rooftop terrace. Located at the Enclave Suites, this unit features a rooftop terrace with views overlooking Sandy Lake. Recently remodeled, it boasts practical functionality with beautiful design. This unit is everything you need to enjoy a vacation in Orlando. It is centrally located off of International Drive and minutes from Universal Studios, Volcano Bay, SeaWorld, Disney World and much more. Enjoy a luxurious stay without the hefty price.

Modern Lake view Condo 1 mile from Disney
You will love our updated 1 bedroom, 2 bathrooms, spacious 798 sq ft condo so close to Disney at Blue Heron Beach Resort in wonderful Lake Buena Vista, home to lots of restaurants and shopping! Enjoy spectacular sunrise views from your private balcony overlooking the lake. Resort amenities include large swimming pool, kiddie pool, hot tub, tiki bar, fitness rooms & game room. Located on peaceful Lake Bryan, you have access to water sports like kayaking, boating, jet skis & fishing on the lake.

Vista Cay Orlando Lakeview Condo
Modern luxury apartment (1800 sqft). 3 bedrooms, 2 bathrooms and 2 living rooms. Self catering. Sheets, pillows, towels, kitchen utensils are provided Corner balcony with view to Sea World Vista Cay has 2 pool areas with a nice club house, exercise room, game room, cinema, tennis/basket Easy checkin - guests receive a code to the condo so they are able to self-checkin without any delay on their arrival Local agent on site that can assist if there are any problems during your stay Free WI-FI

Penthouse Lakeview Minutes to Disney/ Universal
Top floor (21st) PENTHOUSE condo with King bed/ 2 full bathrooms, Full Kitchen & washer/dryer. Sleeps 6. Minutes to Disney & Universal. Penthouse has extra large private balcony with Spectacular LAKE-VIEW. Wood-look tile floors throughout & custom electric fireplace with 65” smart tv. Updated kitchen with granite & SS appliances. Full size washer & dryer. Twin bunkbeds in hallway cove (top bunk has own tv) & super comfy memory foam pullout-sofa in living room. Access to all resort amenities.

Entire Condominium- Luxury Gated Community
Gorgeous, recently renovated 1 bedroom condominium with vaulted ceilings and tons of natural light. This condo has the exclusivity for a single guest or the intimacy for a couple. It is even spacious enough for a small family or group of friends with a Queen Bed and Twin Bed in the bedroom and a comfortable Queen Pull-out bed in the living room. This unit is located in the Heart of Orlando. 8 minutes from the Airport. 25 minutes from Universal. 30 minutes from Disney. 15 minutes from downtown!

Bird’s-Eye View! 2bd/2 King/2Bath Disney Area
2 KING/ 2 BATH/ 2 BALCONY condo for an ideal getaway. Condo located within 10 min. from Disney, 15 min. for Universal, 25 min. to Downtown Orlando, and 1 hr to the beach. From the 12th floor unit, you can enjoy the sunrise over Lake Bryan in the morning and sunset - book the extra day, you’re gonna wish you did. Yep, that's right - your view is SKY HIGH, the best in Central Florida. Unit is fully equipped and very luxurious. Parking included in price and there are NO ADDITIONAL RESORT FEES.

Waterfront Condo minutes to Disney & Universal
Just minutes from Disney World and Universal Studios, this condo places you in the heart of Orlando’s top attractions, including Disney Springs, Islands of Adventure, SeaWorld, Magic Kingdom, Epcot, two outlet malls, and more. Relax on your private balcony with breathtaking views of Lake Bryan, or enjoy the resort-style pool with a full Tiki bar and dining menu. Additional perks include free parking, 24-hour security, and complimentary HBO & Netflix. No deposit required and no extra fees.

Luxury 2B2B APT Near Convention Center, Universal
*Location: On Universal BLVD, right next to International Dr Driving: 2 Min to Orange County Convention Center 7 Min to Sea World 12 Min to Universal Studio 15 Min to MCO airport 18 Min to Disney World Luxury 2b2b APT: (Designed by Danna) 1800 sqft, 2 King beds free community parking, gated community Access to community swimming pool, gym, sports court Free private wifi + spectrum cable TV We provide all supplies including towels, kitchen ware, cleaning supplies, shower supply

Super Mario's Sky Suite - Epic Universe 3 BD SUITE
Welcome to your ultimate Nintendo getaway where every room is artfully and thoughtfully designed with a unique Super Mario theme. From custom decor to playful details, every corner is a tribute to the beloved world of Mario and friends. With classic Nintendo consoles at your fingertips, you’ll have everything you need to relive your favorite gaming memories in style. Unwind, play, and immerse yourself in the colorful world of Nintendo - TRUE SUPER MARIO ENTHUSIASTS ONLY :)

Downtown Condo w/ Treetop Views & Free EV Charging
Rooftop Deck with Skyline Views - Free Downtown Parking - Free EV Charging - Fast WiFi Lots to love about this condo! We are just four blocks from Lake Eola. Plenty of great restaurants and nightlife options close, yet we are just far enough from the noise and traffic of downtown to enjoy some quiet too. Walk to Grocery Store (Publix), Fine Dining, Bars, Clubs, Performing Arts Center, Lake Eola Farmer's Market, Kia Center Concerts and Sporting Events and more!!!

Beautiful Downtown Condo 1/1
This fully furnished 1/1 apartment, comes fully equipped with all the necessities you need for your vacation or short stay to Orlando, The City Beautiful. We have fully remodeled our house and would like to share the experience with you. The bedroom come with California king bed. Our kitchen has pots, pans, plates and silverware, as well as a Nespresso coffee machine for your morning wake up! We have our laundry machines in-house and yes, you can use them.

Lovely Winter Park Home close to Hospitals !
Lovely Condo close to Full Sail, Rollins College, Valencia College, UCF and Advent Health Winter Park Hospital. Close to Park Avenue - Winter Park’s shopping, dining and cultural gem – boasts more than 140 boutiques, sidewalk cafes, and museums, all in the shadow of oak-canopied Central Park. In addition to the shops, dining and cultural offerings, you can plan a trip around special events that include seasonal art shows, concerts and fashion events.
Popular amenities for Winter Park condo rentals
Weekly condo rentals

Classy Disney Themed Condo with FREE shuttle!

2 bedroom Balcony King Suite - Lake & Pool view

Buena Vista The Perfect Location to Theme Parks!

New! Seven Eagles Hideaway at Reunion Resort

New Apartment 3BR - 308 - Convention Center

Modern & Bright • Near Disney & Outlets

2BR Modern Pet-Friendly Condo 6 mins from Disney

Private Home * King Bed Suite *Downtown Orlando*
Pet-friendly condo rentals

Pet friendly Orlando area near ESPN Center

Beautiful Lake View Condo, Vista Cay-1004

Spacious Orlando 2brm condo near Universal &Disney

Magically Close to Disney- Serene LakeView Condo

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

Top Floor Condo Lake View near Disney Storey Lake

Remodeled 2BR/2BA Near Disney, Pool +WiFi +Parking

Disney Adorable Condo in the heart of it ALL! 1/1
Condo rentals with a pool

3/2 near beaches and theme parks

Spacious & new 3 Bedrooms condo | 5mn to Disney

Welcome In! Epic/OCCC/Shingle 1-floor

Stunning Storey Lake Resort near Disney

London House | Orlando Airport Private Condo

XLPatio Studio/KingBed/Universal

Sea World Orlando Apts - Parks/Convention Centre

Private balcony, Disney under 10 mins, Roku+Cable
Quick stats about condo rentals in Winter Park

Total holiday rentals
Explore 10 holiday rentals in Winter Park

Nightly prices starting at
Winter Park holiday rentals start at $83 AUD per night before taxes and fees

Verified guest reviews
Over 380 verified reviews to help you choose

Holiday rentals with a pool
10 properties feature pools

Wi-Fi availability
10 of Winter Park holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winter Park rentals

4.9 Average rating
Winter Park stays are highly rated by guests—averaging 4.9 out of 5!

Nearby attractions
Winter Park's top spots, include Orlando Science Center, Harry P. Leu Gardens, and Orlando Museum of Art
Destinations to explore
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- Rentals with pools Winter Park
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- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
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- Orange County Convention Center
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- Daytona Beach Bandshell
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- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
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