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Condo vacation rentals in Winter Park

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Top-rated condo rentals in Winter Park

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A light-filled seating area features two plush chairs with decorative pillows, positioned near a large window dressed in soft curtains. A potted plant adds a touch of greenery, while a stylish rug lays on the hardwood floor, enhancing the overall cozy ambiance.

Condo in South Eola

4.82 out of 5 average rating, 111 reviews

2/2 PENTHOUSE DOWNTOWN with large Billiard room

This fully renovated mid century beauty has all the necessities you will need for your long vacation or short stay in Orlando. The Penthouse has 2 bedrooms with king size beds, and two full bathrooms. The unit also has a large billiard room, with TV where all streaming services are available. Kitchen comes with oven, pots, plates.... and a Nespresso machine with free pods for your morning wake up. Washer/dryer are available. *we ask our guests to make inquiries before booking the apartment*

A panoramic view captures the lush Arnold Palmer PGA golf course along with the resort pool area featuring a hot tub. The vibrant Star Wars themed bedroom includes wall decorations and arcade features. Inside, a cozy living area is showcased with a large TV and French doors leading outside.

Condo in Kissimmee

4.96 out of 5 average rating, 158 reviews

Fireworks Penthouse: Top Floor, Star Wars, 2 Pools

This modern 3-bedroom TOP FLOOR (with an ELEVATOR right to the door) luxury condo has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

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.

Condo in Ventura

4.83 out of 5 average rating, 117 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 dining area on a spacious terrace features a wrought-iron table with seating for six. The table is set with plates, glasses, and utensils, accompanied by a bottle of sparkling wine. A large umbrella provides shade, with distant views of nearby buildings.

Condo in Orlando

4.86 out of 5 average rating, 290 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.

A spacious studio features a king-sized bed adorned with soft linens. A round dining table with stylish blue chairs is positioned nearby, alongside a vibrant decorative rug. Large windows provide natural light, framed by flowing gray curtains, while a modern chandelier hangs above, enhancing the elegant decor.

Condo in Orlando

4.88 out of 5 average rating, 234 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. FREE PARKING. -Universal Studio 8 minutes by car -Disney park’s 10 to 15 minutes by car. Airport 15 minutes by car. -Seaworld Park’s 8 minutes.

The master bedroom suite is spacious and features a king size bed adorned with blue and white accents. Two lamps are positioned on each side of the bed, with artwork displayed above. Natural light enters through the window, and a private bathroom can be seen through the open door.

Condo in Orlando

4.96 out of 5 average rating, 183 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

A vibrant living area features a Super Mario-themed mural depicting iconic characters against a blue backdrop. Plush seating surrounds a coffee table styled with bright colors, while a playful rug showcases a character from the Mario universe, creating a fun and inviting atmosphere for relaxation and gaming.

Condo in Orlando

4.93 out of 5 average rating, 121 reviews

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 :)

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.

Condo in South Eola

4.97 out of 5 average rating, 146 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!!!

A modern living area features a cozy sectional sofa paired with vibrant yellow armchairs. A patterned area rug sits beneath a coffee table, while natural light fills the space through sliding glass doors that provide access to the outdoor balcony.

Condo in Winter Garden

4.92 out of 5 average rating, 104 reviews

Spacious Condo 15min to Disney with private patio!

Spacious 3 bedrooms condo with outdoor dining and hanging out area located at the Palisades Condominiums in Winter Garden Conveniently located on the luxurious west side of Disney, just a 15-20 mins drive to Disney parks, close to other major theme parks, restaurants and supermarkets. This luxury condo is spacious, modern, and has everything that you'll need for your stay! The kitchen is fully equipped to prepare your meals and enjoy it on your private balcony

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.

Condo in South Eola

4.86 out of 5 average rating, 148 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.

Top guest favorite

The living area is furnished with a blue couch adorned with patterned pillows. Two matching wooden side tables with lamps provide soft lighting, while a wooden coffee table sits in the center. A decorative wall piece featuring palm trees adds a touch of character to the room.

Condo in Orlando

5 out of 5 average rating, 145 reviews

Disney & Epic Free Shuttle, Kitchen

Enjoy a remodeled condo with free shuttle to Disney and Universal, all just minutes away! What’s Included: • 2 Queen Beds • Full Kitchen • Free Keurig Coffee • 55” TV's • Fast Wi-Fi • Free Parking • Heated Pool & Hot Tub • Free Shuttle • Self Check-In Ideal for families, couples, or solo travelers looking to relax after the parks. Disney Springs Magic Kingdom Hollywood Studios Animal Kingdom EPCOT Epic Universe Universal SeaWorld Premium Outlet Mall

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.

Condo in Winter Park

4.83 out of 5 average rating, 104 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.

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Popular amenities for Winter Park condo rentals

Free parking on premises

Air conditioning

Weekly condo rentals

A spacious living area features a light-toned sectional sofa facing a large flat-screen television. Two comfortable blue armchairs are positioned at a small table by the window, which allows natural light to illuminate the space. A decorative area rug enhances the wood flooring.

Condo in Orlando

4.93 out of 5 average rating, 14 reviews

Epic Universe Vacation Condo, Vista Cay - 2017

A spacious living room features an elegant coffee table positioned on a light rug. Soft, neutral-toned sofas are adorned with decorative pillows. Natural light fills the space through multiple windows, and a ceiling fan enhances airflow. Kitchen and dining areas are visible in the background.

Condo in Reunion

4.93 out of 5 average rating, 28 reviews

Marvelous corner condo at Reunion Resort in ideal

A serene bedroom features a large bed adorned with plush pillows and a textured blanket. A bedside table holds a small potted plant, complemented by a wall with palm tree motifs and wooden paneling. Soft lighting creates a calming ambiance.

Condo in Kissimmee

4.96 out of 5 average rating, 45 reviews

relaxing lake view escape

Top guest favorite

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, 15 reviews

Stunning waterfront Views, 1 mile to Disney 2 bath

A serene view of downtown Orlando is captured at dusk, showcasing colorful reflections on a calm lake. City buildings are illuminated against a vibrant sky featuring soft purple and pink hues, creating a peaceful ambiance.

Condo in Orlando

4.94 out of 5 average rating, 51 reviews

London House | Orlando Airport Private Condo

A spacious living area is featured, furnished with a light gray sectional sofa and matching ottoman. Natural light floods in through large windows, illuminating the room. A dining area with a wooden table and chairs is visible, complemented by decorative plants throughout.

Condo in Lake Mary

4.71 out of 5 average rating, 24 reviews

Entire Condo in Lake Mary 3/2 w/dedicated office

A modern living area features a light-colored couch adorned with decorative pillows, complemented by two blue armchairs. A geometric area rug adds texture beneath a central coffee table. Light fixtures illuminate the space, enhancing its contemporary design and inviting ambiance.

Condo in Windermere

4.94 out of 5 average rating, 47 reviews

LuXury Apt with Lake View, Cable & fast WiFi

Top guest favorite

An open-concept kitchen features a large island with three stools, surrounded by modern cabinetry and stainless-steel appliances. Natural light fills the space, complementing the neutral wall tones and wooden flooring. A hallway leads to additional areas of the condo, enhancing the spacious feel.

Condo in Orlando

5 out of 5 average rating, 16 reviews

Orlando Convention Center at Vista Cay

Pet-friendly condo rentals

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, 130 reviews

Vista Cay Luxury Vision, Walk to EPIC and OCCC

A bright living area is showcased, featuring a light-colored leather sofa with yellow accent pillows. Soft natural light streams through the window, illuminating a round coffee table with decorative items. A work desk and chair are visible in the corner, alongside a comfortable armchair.

Condo in Kissimmee

4.85 out of 5 average rating, 92 reviews

*NEW*• Modern Luxury Condo

A warm living space features a dark wooden ceiling and an accent wall with textured concrete. Comfortable seating faces a mounted television, while wooden shelves are adorned with books and decorative plants. Natural light enters through large windows, enhancing the inviting atmosphere.

Condo in Orlando

4.85 out of 5 average rating, 80 reviews

5 mins Universal 10 mins Epic park | Rustic LOFT

A spacious guestroom features a king size bed with white linens and decorative pillows. An accent wall in orange adds a vibrant touch. A bedside table with a lamp is positioned on either side of the bed. A portable crib is placed at the foot of the bed.

Condo in Kissimmee

4.77 out of 5 average rating, 261 reviews

King Bed Small Studio Disney World Universal

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, 114 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

4.91 out of 5 average rating, 153 reviews

Amazing Clean Studio near Conventions & Disney

A clear view of a pool surrounded by lounge chairs and palm trees, reflecting the sunlight. Umbrellas provide shade, and green lawns are visible in the background. The calm water enhances the serene environment, creating a relaxing outdoor space.

Condo in Kissimmee

4.82 out of 5 average rating, 209 reviews

Family Friendly I Mins from Disney I Resort Pool

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, 122 reviews

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

Condo rentals with a pool

Top guest favorite

A decorative display featuring a Mickey Mouse-shaped shelf with a deck of Bicycle playing cards. The shelf is flanked by two potted green plants, placed on a textured runner that complements the natural elements of the arrangement.

Condo in Orlando

5 out of 5 average rating, 58 reviews

Classy Disney Themed Condo with FREE shuttle!

Condo in Orlando

4.64 out of 5 average rating, 376 reviews

INTERNATIONAL dr/UNIVERSAL 2 Bedroom CONDO-HOTEL

The open-concept living area features a leather sectional sofa facing a flat-screen TV mounted on a wall with an accent arch. A round coffee table is positioned between the seating and a dining area in the background, complemented by green armchairs and decorative plants.

Condo in Lake Nona

4.86 out of 5 average rating, 22 reviews

Near MCO, USTA and Lake Nona Medical City

A spacious bedroom features a large bed with crisp white linens and colorful accent pillows. The backdrop is adorned with a striking mural, while natural light enters through a nearby window, framed by black curtains. A bedside table adds functionality to the space.

Condo in Orlando

4.88 out of 5 average rating, 48 reviews

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

A bright living area features a cozy gray sofa paired with two stylish yellow chairs. A wooden coffee table sits atop a textured area rug, while large glass doors lead to a balcony that offers views of Lake Bryan.

Condo in Orlando

4.97 out of 5 average rating, 98 reviews

Modern Lake view Condo 1 mile from Disney

Top guest favorite

A private balcony offers serene lake views overlooking the sparkling pool. Stylish outdoor seating provides a comfortable place to relax, with modern decor elements visible inside the living space through the sliding glass doors.

Condo in Orlando

5 out of 5 average rating, 73 reviews

Retro Theme! 10 min from Disney! Lake View! MCM

A vibrant pool area is surrounded by palm trees and well-maintained landscaping. The four-story building features multiple balconies overlooking the pool. Numerous lounge chairs in bright colors are arranged around the swimming area, inviting relaxation under a clear blue sky with scattered clouds.

Condo in Orlando

5 out of 5 average rating, 3 reviews

Two Bedroom Jacuzzi/Pool/Balcony/Water Park/Gym 05

Top guest favorite

A bright living area showcases large glass doors that open to a balcony with views of the lake. A comfortable couch is complemented by a coffee table, while a dining table with black chairs accommodates multiple guests. Natural light fills the space, enhancing the decor.

Condo in Orlando

4.98 out of 5 average rating, 41 reviews

Beautiful Lake & Disney Views. Stylish 2 Bedroom

Quick stats about condo rentals in Winter Park

Total rentals
10 properties
Nightly prices starting at
R716 ZAR before taxes and fees
Total number of reviews
350 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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