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Condo vacation 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.

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Condo in Kissimmee

4.93 out of 5 average rating, 195 reviews

3150-303 Resort Pool View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 6 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

Condo in Orlando

4.72 out of 5 average rating, 453 reviews

Lake-front view at International Drive & Universal

Renovated Studio Apt with full size balcony, lake-front view & view of Universal Orlando. Located in heart of International Drive. World-class dining, attractions, shopping, entertainment & nightlife all within walking distance. Fully remodeled with many upgrades. Fully furnished with full-size refrigerator, kitchenette, queen bed, & sofa bed! Community has 3 pools & hot tubs, restaurant, basic gym, tennis, laundry facility ($), free wifi & free onsite parking. No "resort fee" or hidden charges.

A well-equipped gym area features a rack of dumbbells in varying weights positioned beside a colorful selection of smaller weights. The space is illuminated by natural light from nearby windows, and mirrors enhance the area’s openness.

Condo in Ventura

4.83 out of 5 average rating, 115 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!

A modern kitchen features sleek stainless steel appliances, including a refrigerator and microwave. The countertop is adorned with light-colored granite, complementing the white cabinetry. A coffee maker and toaster sit on the countertop, providing convenience for guests.

Condo in Orlando

4.86 out of 5 average rating, 284 reviews

🕶Your Private Terrace In The Sky🕶 Great Views

Great location for Universal Studios and EPIC, the Convention Center and amazing restaurants. This beautiful 2/2 apartment isone of the nicest at The Enclave Hotel & Suites. Relax on your own spacious private terrace while enjoying 270° views over Universal Studios, International Drive and the Orlando Eye. Newly renovated with Granite and travertine throughout. Stainless steel appliances and oversized smart TVs. Hotel amenities include indoor and outdoor pools, tennis, food court, pub and gym.

The dining area displays a spacious layout with multiple wooden tables and chairs arranged throughout. Soft lighting from hanging fixtures creates a welcoming environment. Walls are adorned with neutral tones and a large television is visible in the background, enhancing the communal dining experience.

Condo in Orlando

4.82 out of 5 average rating, 400 reviews

NICE SUITE NEAR UNIVERSAL/DISNEY/CONVENTION CENTER

The suite is spacious, very nice with swimming pool view from windows and located just one block from famous international Drive. The suite is just walking distance to shops, nightlife, restaurants, boutiques, easy access to the Orlando International Airport and close to all orlando major attractions: Convention center (5 min.) Universal/vocano bay (7 min.), Disney world (15 min.), Seaworld (7 min.), Millenia Mall & Outlet mall (10 min.) and Orlando international airport (20 min). FREE PARKING

A well-lit pool area is featured, showcasing a curved swimming pool with clear blue water. Surrounding amenities include several lounge chairs and palm trees. The building in the background contains multiple balconies, reflecting warm light from the interior.

Condo in Orlando

4.87 out of 5 average rating, 223 reviews

Maria Luz Studio-Huge Terrace/Universal area.

We are sure that you will fall in love with our STUDIO!! Beautiful, Romantic and incredible lake view Studio!! King side bed and sofabed. Enjoy a LARGE PRIVATE TERRACE. Enjoy the jacuzzi bathtub inside the bathtub. Our Studio is located one block from the famous International Dr. In Orlando City. In the center of everything!!Universal Studio’s area. -Universal Studio 8 minutes by car. -Disney park’s 10 to 15 minutes by car. -Airport 15 minutes by car. -Seaworld Park’s 10 minutes by car.

An open kitchen area features a marble countertop with a modern sink and decorative blue flowers. Pendant lights hang above, illuminating the space. The living area is visible in the background, showcasing a spacious layout with comfortable seating and large windows allowing natural light.

Condo in Orlando

4.96 out of 5 average rating, 180 reviews

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

Two teal accent chairs are positioned facing large windows that offer expansive views of the skyline and surrounding greenery. A small round table sits between the chairs, adding functionality to the inviting seating area. A potted plant enhances the space with a touch of nature.

Condo in Orlando

4.97 out of 5 average rating, 140 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!!!

Top guest favorite

Condo in Orlando

4.86 out of 5 average rating, 146 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.

A modern living area features a sleek black sectional sofa positioned alongside a minimalist coffee table. Above, three framed artworks add visual interest, while potted plants provide a touch of greenery. Natural light filters through vertical blinds, enhancing the bright and airy ambiance.

Condo in Orlando

4.86 out of 5 average rating, 144 reviews

UPSCALE townhouse minutes to all attractions

LOCATION! LOCATION! LOCATION! You are going to be centrally located to all Orlando has to offer *Universal Studios less than 8 minutes *Seaworld is 7 minutes away *Disney world 18 minutes *Premium outlets about 8 minutes *MCO airport 20 minutes Conveniently located near major highways to commute anywhere in Orlando. The space is Fully renovated. There are 2 floors in this townhouse, the unit has a central AC that you can set your desired temperature to.

A functional kitchen area features a compact refrigerator, microwave, and coffee maker. The adjacent living space includes a comfortable sofa, dining table with chairs, and natural light flowing from large windows that allow a view of the balcony.

Condo in Orlando

4.89 out of 5 average rating, 131 reviews

Studio close to Universal Studios + free Netflix

Renovated studio on I-Drive in 'The Enclave Hotel and Suites', free NETFLIX + parking Located 5 minutes from EPIC UNIVERSE and UNIVERSAL STUDIOS *no early check ins/late check outs, luggage hold/drop off or free mail/package delivery. Check out the page: usebounce *Please read entire listing/house rules. *The buildings have been renovated on the outside but on the inside they are very dated. If you are looking for a modern building this isn't it

A spacious terrace overlooks the surroundings, featuring a hanging chair and lounge chairs for relaxation. A patio umbrella provides shade, while a small table sits nearby. The area is designed for outdoor enjoyment with light-colored flooring and an inviting atmosphere.

Condo in Orlando

4.85 out of 5 average rating, 483 reviews

Modern Studio with Private Terrace near Universal

Modern and spacious studio, intimate, relaxing and quiet with spectacular lake and pool views from a private large terrace.Perfectly located for the best possible Orlando vacation experience! It is just off International Drive close to Major Attractions, Dining and Shopping. Located only 5 minutes from Universal Studios/Epic Universe and 15 minutes to Disney Parks . Two Outdoor heated pools , 24hr security. No deposit required and no extra fees!

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Popular amenities for Winter Park condo rentals

Free parking on premises

Air conditioning

Condo rentals with a pool

Top guest favorite

Condo in Orlando

4.92 out of 5 average rating, 103 reviews

Waterfront Condo minutes from Disney & Universal

An aerial view showcases a vibrant resort complex set against a serene lake. Multiple pool areas, embellished with palm trees and lounge chairs, create inviting spaces for relaxation. The colorful buildings surrounding the pool contribute to the tropical ambiance, reflecting the charm of the destination.

Condo in Orlando

4.86 out of 5 average rating, 116 reviews

Marriott Grande Vista Luxury Studio-like

Top guest favorite

An inviting bedroom features a Mickey-themed design with two spacious beds, ideal for children. The cozy living area showcases a comfortable sectional sofa, a flat-screen TV, and modern lighting. A stylish dining space with a table and six chairs is also visible, enhancing communal dining.

Condo in Kissimmee

5 out of 5 average rating, 6 reviews

4731-103 Stay Magical • 2BR with Mickey Room & Mor

Top guest favorite

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.

Condo in Orlando

4.95 out of 5 average rating, 86 reviews

Penthouse Lakeview Minutes to Disney/ Universal

Top guest favorite

Aerial view showcasing the expansive resort complex, featuring multiple buildings surrounded by lush greenery. The central area includes a large shaped pool surrounded by lounge chairs and sun umbrellas, alongside a mini-golf area and pathways connecting various amenities.

Condo in Lake Buena Vista

4.94 out of 5 average rating, 63 reviews

Grand Villas Resort 2 bedrooms

The illuminated pool area features clear blue water reflecting the vibrant colors of dusk. Surrounding palm trees create a tropical ambiance, while lounge chairs are arranged nearby. The serene waterfront view highlights the transitioning sky, offering a peaceful retreat at twilight.

Condo in Orlando

5 out of 5 average rating, 8 reviews

Stunning waterfront Views, 1 mile to Disney 2 bath

A stylish studio is featured with a queen bed and a sofa bed, offering a spacious layout. Large windows provide views of a serene lake and surrounding attractions. Modern décor includes a flat-screen TV, with amenities like a fully equipped kitchenette visible in the corner.

Condo in Orlando

4.85 out of 5 average rating, 81 reviews

#2608 Lakeview Luxury Condo by I-Drive/Universal

Top guest favorite

A spacious living area is highlighted by a large flat-screen TV mounted on the wall. Comfortable seating options include a gray sectional sofa and blue accent chairs. Light wood accents complement the open layout, which connects to a well-equipped kitchen visible in the background.

Condo in Orlando

4.97 out of 5 average rating, 65 reviews

Scenic View Condo Near Disney

Weekly condo rentals

Top guest favorite

Condo in Orlando

5 out of 5 average rating, 52 reviews

Classy Disney Themed Condo with FREE shuttle!

Condo in Apopka

5 out of 5 average rating, 4 reviews

Luxury Apt :08 to Kelly Springs- Accommodates 8

Condo in Orlando

4.84 out of 5 average rating, 50 reviews

Lovely 2/2 Thorton Park Condo w/ secure parking

Three labeled amber bottles are mounted on the shower wall, containing shampoo, conditioner, and body wash. The bottles are arranged in a row, providing easy access to toiletries. The backdrop features textured gray tiles, creating a clean and organized bathroom aesthetic.

Condo in Orlando

5 out of 5 average rating, 50 reviews

Boho Retreat: 7 min to Universal & Epic!

A modern communal lounge area is featured, showcasing white sofas arranged around a circular table. A large television is mounted on the textured dark wall. Windows provide natural light, while glass doors open to an outdoor seating area, enhancing the inviting atmosphere.

Condo in Kissimmee

4.94 out of 5 average rating, 17 reviews

Carri-Vision Suite, (Theme-Parks)Orlando/Kissimmee

Condo in Orlando

4.86 out of 5 average rating, 43 reviews

King Bed/13-16 min Disney & Epic/Pool/Hot Tub

A modern high-rise condominium is shown overlooking a serene blue lake. The building features multiple floors with balconies, and palm trees line the entrance. A parking area is visible beneath the building. The surrounding landscape includes lush greenery, enhancing the peaceful setting.

Condo in Orlando

4.97 out of 5 average rating, 93 reviews

Modern Lake view Condo 1 mile from Disney

Condo in Central Business District

4.93 out of 5 average rating, 30 reviews

FL King Velvet Suite- 3bdrm/2Bath-2000 sq ft

Pet-friendly condo rentals

A modern living area showcases a mix of comfortable seating, including a plush blue couch and a tan sofa, arranged around a stylish, round ottoman. A large television is mounted above a lighted console, and natural light filters through the nearby window, enhancing the warm decor.

Condo in Osceola County

5 out of 5 average rating, 18 reviews

V.I.P Luxury 5 stars Disney 15 mns

The open-plan living area features a spacious dining table surrounded by elegant chairs, complemented by designer lighting. A comfortable sectional sofa is positioned opposite a large TV, while large windows allow natural light to illuminate the room.

Condo in Orlando

4.95 out of 5 average rating, 126 reviews

Vista Cay Luxury Vision Walk to EPIC and OCCC

The living room features a spacious sectional sofa and a flat-screen TV mounted on a wooden console. Large glass doors provide a view of the patio and golf course, while natural light fills the room through the sheer curtains. A potted plant adds a touch of greenery.

Condo in Kissimmee

4.94 out of 5 average rating, 116 reviews

3 Bedroom w/large patio on Resort Golf Course

A tranquil waterfront view presents a vast lake reflecting soft pastel colors of sunset. A fishing pier extends into the water, surrounded by lush greenery. The serene scene invites relaxation, showcasing the natural beauty of Lake Bryan.

Condo in Orlando

4.99 out of 5 average rating, 138 reviews

Serene Lakeview By DisneyWorld -Universal Stds 8mi

A designated pet area is shown, featuring two stainless steel bowls placed on a wooden stand beside a soft dog bed. The floor is finished in a light wood tone, enhancing the area’s functionality for pet owners.

Condo in Celebration

4.9 out of 5 average rating, 111 reviews

Pet Friendly in Orlando Area near Disney.

A spacious studio room features a plush queen bed dressed with vibrant linens. Nightstands with lamps are positioned on either side of the bed. A mirror and a desktop chair complement the modern decor, while a colorful cityscape artwork adds a pop of color to the wall.

Condo in Orlando

4.9 out of 5 average rating, 146 reviews

Amazing Clean Studio near Conventions & Disney

A stunning water park showcases multiple pools and attractions surrounded by palm trees. The lazy river winds through the landscape, while vibrant water slides stand ready for enjoyment. Ample lounging space is offered for relaxation, highlighting the inviting atmosphere of this recreational area.

Condo in Davenport

5 out of 5 average rating, 6 reviews

Stunning 3BR Condo Near Disney

The master bedroom features a spacious bed with a tufted headboard, complemented by a decorative mirror and framed artwork. Natural light streams in through a large window, revealing views of greenery. A warm color palette and wood accents create a relaxing atmosphere.

Condo in Kissimmee

4.95 out of 5 average rating, 113 reviews

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

Quick stats about condo rentals in Winter Park

Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
320 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
10 properties have a dedicated workspace

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