Apartment holiday rentals in Winter Park

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Top-rated apartment rentals in Winter Park

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

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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, 119 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 large community pool is surrounded by lounge chairs and shaded umbrellas, with clear blue water reflecting the sky. Fenced areas and palm trees offer a serene environment, while a peaceful lake can be seen in the background, completing the setting.
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!

Guest favourite
The open living area is furnished with a comfortable sofa and a modern coffee table, complemented by a large flat-screen TV mounted on the wall. Natural light flows in through glass doors, leading to a balcony. A serene color palette and light wood flooring create a welcoming environment.
Apartment in Kissimmee
4.87 out of 5 average rating, 119 reviews

3176-301 Resort 2BR Apt by Disney World Orlando

Just minutes from DISNEY WORLD ORLANDO FLORIDA, fully renovated 2bed/2bath & fully equipped apartment for up to 6 guests, located in the family friendly Secret Lake Resort. Master suite has a KING bed & 65" Smart TV. Second bedroom has 2 Full beds and a 40" Smart TV. The open floor plan blends Kitchen, Dining and Living room with a 70" Smart TV. Close to Parks, Margarita Ville Water Park, Outlet malls & Retail stores. All amenities included: Wi-Fi, Pool, Gym & BBQ area. NO RESORT FEES

Guest favourite
Apartment in Kissimmee
4.87 out of 5 average rating, 104 reviews

Magical Disney's Minion themed & Water View 3161

Indulge in our magical vacation homes, fully equipped for your comfort. With spacious bedrooms & full equiped kitchens, just minutes from Disney's theme parks. Book your stay for 7 days or more and unlock an exclusive 5% discount ! Craft unforgettable memories with loved ones at Disney World. For extended stays of a month or more, enjoy an even greater 10% discount as part of our long-stay offer. (Discount will apply on selected stays) Reserve now! we would love to be your host!

Superhost
Apartment in Orlando
4.75 out of 5 average rating, 111 reviews

Prime Location 3BR Condo near Epic Universe!

Step into your ultimate Orlando adventure base! This roomy 3BR condo at Vista Cay puts you just minutes from the brand-new Epic Universe theme park, plus Universal Studios, Magic Kingdom, and all the action on International Drive. Lounge on your private balcony with sweeping views, cool off in the resort pool, fire up the BBQ, or hit the gym. With fast WiFi, EV charging, free parking, and lake access, you’re set for an unforgettable stay packed with thrills and chill.

Guest favourite
Apartment in Orlando
4.83 out of 5 average rating, 138 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!!

Top guest favourite
Apartment in Orlando
4.96 out of 5 average rating, 172 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 living area features a large sectional sofa and a glass coffee table. Natural light floods the space through multiple windows, enhancing the warm wooden flooring. A round dining table is set for four, while a decorative artwork piece adorns the wall.
Apartment in Orlando
4.87 out of 5 average rating, 178 reviews

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.

Guest favourite
An aerial view captures the centrally located pool surrounded by landscaped gardens and palm trees. The octagonal-shaped pool is bordered by a smooth stone deck, with lounge areas and a gazebo visible nearby. The surrounding buildings exhibit a harmonious architectural style.
Apartment in Winter Park
4.85 out of 5 average rating, 123 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.

Top guest favourite
A spacious terrace features comfortable lounge chairs with blue cushions and a stylish hanging chair. A small table accompanies two chairs, providing a perfect spot for relaxation. An umbrella offers shade, while the expansive view overlooks the surrounding area, enhancing the outdoor experience.
Apartment in Orlando
4.87 out of 5 average rating, 555 reviews

Lakefront Studio •Private Terrace• near Universal

Modern, spacious, and serene, this studio offers beautiful lake and pool views from your own private terrace—perfect for unwinding after a day of adventure. Ideally located just off International Drive, you’ll be close to Orlando’s top attractions, dining, and shopping. Enjoy unbeatable convenience with Universal Studios/Epic Universe only 5 minutes away and Disney Parks just 15 minutes away. No deposit required and no extra fees.

Guest favourite
Apartment in Orlando
4.74 out of 5 average rating, 364 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.

Superhost
Apartment in Orlando
4.88 out of 5 average rating, 169 reviews

Vista Cay Luxury Prize, Next to EPIC and OCCC

Spacious 3 Bedroom/2 Bathroom 4th floor corner condo. Sleeps 6. Nice 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.

Popular amenities for Winter Park apartment rentals

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 £45 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

  • 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

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