Apartment holiday rentals in Winter Park

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Quick stats about apartment rentals in Winter Park

Total holiday rentals
Explore 10 holiday rentals in Winter Park
Nightly prices starting at
Winter Park holiday rentals start at £30 per night before taxes and fees
Verified guest reviews
Over 470 verified reviews to help you choose
Holiday rentals with a pool
10 properties feature pools
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 of Winter Park holiday rentals include wifi 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

Top-rated apartment rentals in Winter Park

Guests agree: these apartments are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Orlando

4.95 out of 5 average rating, 137 reviews

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.

Top guest favourite

The living room features large sliding glass doors that open to the balcony, providing a view of the lake. A contemporary electric fireplace sits beneath a 65-inch smart TV. Comfortable seating includes a sofa, an armchair, and a coffee table, with warm curtains adding a touch of color.

Apartment in Orlando

4.96 out of 5 average rating, 126 reviews

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.

Guest favourite

A spacious living area is showcased with a comfortable gray sofa and a round coffee table placed on a light blue area rug. Modern wall art adorns the walls, and a dining table with four chairs is visible in the background. Natural light fills the space, highlighting the vaulted ceilings.

Apartment in Orlando

4.84 out of 5 average rating, 127 reviews

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!

Top guest favourite

A modern living area features a spacious layout with large windows showcasing expansive lake views. A comfortable blue chair sits next to a small table, and a sleek couch complements the light-colored walls. The area is illuminated by natural light, creating a bright atmosphere.

Apartment in Orlando

4.92 out of 5 average rating, 138 reviews

2-bedroom condo w/ stunning lake and Disney views

Enjoy a stylish and comfortable stay at our modern 2 bedroom lakefront condo located at the Blue Heron Resort, which offers spectacular lake views and a very convenient and private alternative to neighboring resorts in Lake Buena Vista (perfect location for Disney attractions). Beautifully designed and furnished, our condo features an open plan living room, dining room and a full modern kitchen with stainless steel appliances. Stunning views of a lake and Disney fireworks from 2 balconies.

Guest favourite

The living area is brightened by large windows offering views over the lake. A comfortable sofa and seating area complement a dining table set for six. A television is positioned adjacent to a ceiling fan, creating a welcoming space for relaxation and dining.

Apartment in Orlando

4.93 out of 5 average rating, 236 reviews

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.

Guest favourite

A spacious outdoor pool is surrounded by lounges, with lush greenery and palm trees framing the scene. In the background, a multi-story condominium building is visible, set against a clear blue sky and soft clouds.

Apartment in Orlando

4.79 out of 5 average rating, 266 reviews

Beautiful Apartment 2 Bed 2 Bath Epic/ Universal

This cozy apartment is located in the best place of Orlando, near to all the fun and entertainment. You will love to stay just minutes away from Universal Studios, Icon Park, Sea World, Volcano Bay, Disney, restaurants, Outlets, gift stores and grocerie stores, enjoy Orlando at night at Mangos Tropical or the Diner Pirates Show which is across the street. Our place has 2B/ 2B just steps to the pools. The master has 1 Queen bed, the second bedroom has 2 Twin beds, each one has a TV

Guest favourite

Apartment in Orlando

4.83 out of 5 average rating, 148 reviews

Cozy space 5/10 universal & epic

Take it easy at this unique oasis and tranquil getaway that is located in the heart of Orlando!! Want to have fun?! Literally walking distance from Universal Studios, Want to go shopping?! 5 mins from Millenia Mall and Premium Outlets. Want to experience Orlandos hottest nightlife or stroll through the city it’s 15 mins from Downtown , Do you want to meet Mickey Mouse or shamu?! 15 mins from Disney and sea-world. Even take a dip in the complex pool or play tennis!!

Guest favourite

A spacious living area features a comfortable sofa and two turquoise chairs, inviting relaxation. A large rug with geometric patterns anchors the space, while a modern art piece adds a colorful focal point. Natural light floods in through large windows, highlighting the open layout.

Apartment in Orlando

4.96 out of 5 average rating, 174 reviews

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!!!

Guest favourite

A modern kitchen is seen, featuring white cabinetry and a speckled granite countertop. Stainless steel appliances, including a microwave and toaster, are positioned conveniently. A small potted plant adds a touch of greenery, while natural light filters in through the window above the sink.

Apartment in Winter Park

4.83 out of 5 average rating, 127 reviews

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.

Guest favourite

A bright and airy studio is showcased with large windows allowing natural light to fill the space. A king-size bed with a patterned quilt is paired with a comfortable daybed. A 65" TV is mounted on the wall, and a small dining area features two chairs with a vase of flowers.

Apartment in Orlando

4.79 out of 5 average rating, 108 reviews

XLPatio Studio/KingBed/Universal

2 miles from Universal Studios, 4 miles from SeaWorld, 9 miles from Disney, and 15 miles from Orlando International Airport . Located right on the famous International Drive . Steps away from Universal CityWalk . Oversized balcony with a partial fireworks view . King-size bed and a comfortable daybed . Mini kitchen . 65" 4K TV . High-speed WiFi . 24-hour self-check-in . Free parking . Access to resort pools and amenities

Guest favourite

Apartment in Orlando

4.74 out of 5 average rating, 367 reviews

Retro lake Eola 1 Bedroom Condo Thornton park

Rental agreement needs to be e-signed before check in & ID submitted for legality. Info will not be shared. Check in information will not be shared unless rental agreement is signed and valid ID submitted. Parking: There is 1 designated spot Affordable, no-frills stay in an amazing location. Clean, simple, and budget-friendly — perfect if you value location over luxury. Please be respectful owner lives on property.

Guest favourite

Apartment in Orlando

4.94 out of 5 average rating, 174 reviews

Vista Cay Luxury Vision, Next to EPIC and OCCC

Spacious 2100sf 3 Bedroom/2 Bathroom 4th floor corner condo. Sleeps 8. Large balcony w/seating. Close to Pool/Clubhouse. NEXT TO EPIC, OCCC, Supermarket, Walgreens, Tourist attractions and restaurants. Minutes to Universal Studios, Disney, Aquatica, Discovery Cove & SeaWorld. Upgraded with new flooring, furniture & decor. Free resort amenities & free self-parking for several cars. Dog friendly, for nightly pet fee.