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Apartment holiday rentals in Winter Park

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Top-rated apartment rentals in Winter Park

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Apartment in Orlando

4.82 out of 5 average rating, 294 reviews

Completely renovated + amazing location

Enjoy your stay in this newly renovated apartment with a fantastic location, 1.2 miles to The Mall at Millenia, less than 10 min. drive to Universal Studios or the Premium Outlets, 20 min. drive to Disney area Enjoy entire house in complete privacy, beautiful fully equipped kitchen to make light meals, breakfast bar, walk-in closet, completely renovated bathroom, all in a gated community. FREE PARKING! right in front of your apartment. No additional fees. : : Enhanced cleaning protocol : :

21–28 May

$158 SGD per night

Guest favourite

Apartment in Kissimmee

4.97 out of 5 average rating, 160 reviews

New Lovely 3-bedroom Condo 5 minutes from Disney’s

This is a totally remodel Beautiful Condo! Nice small community with heated pool, fitness center, barbecue area, tennis courts in a quiet private park like setting! Enjoy breakfast on a comfortable screened balcony overlooking a serene conservation area. This 3/2 First floor condo is in a perfect location, just 5 miles from Disney World with lots of shopping & restaurants close by...for golfers, the property is surrounded by lots of beautiful courses, don't delay schedule your Vacations today!

23–30 Sep

$149 SGD per night

Guest favourite

Apartment in Orlando

4.87 out of 5 average rating, 200 reviews

Airbnb's Choice- Best at Blue Heron- Stunning View

"Airbnb's Choice" - When it was time for Airbnb to select a home to feature in their Instagram ad campaign, of the hundreds of homes in the Orlando area, they selected this one. "Shouldn't it be your choice as well?" Tastefully and professionally decorated - This is a spacious one-bedroom, two-bath lakefront condominium located at the Blue Heron Beach Resort. It's conveniently located just two blocks off I-4 and just 1 mile from the entrance to Disney with breathtaking views of Lake Bryan.

19–26 Jun

$188 SGD per night

Guest favourite

Apartment in Orlando

4.91 out of 5 average rating, 150 reviews

Huge/Terrace Studio. Universal Studios 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.

27 Dec – 3 Jan

$188 SGD per night

Guest favourite

Apartment in Orlando

4.81 out of 5 average rating, 342 reviews

Luxury Apt on I-Drive & view of Universal Orlando

Renovated Studio Apt with balcony, pool view & view of Universal Orlando Resort. Located in the heart of International Drive. World-class dining, attractions, shopping, entertainment & nightlife are walking distance. Condo was recently remodeled with several upgrades. Fully furnished with full-size refrigerator, kitchenette, queen bed & balcony. Community has 3 pools & hot tubs, restaurant, C-store, gym, laundry, & free on-site parking. No "resort fee." 3rd party shuttle ($) to parks.

20–27 Oct

$113 SGD per night

Guest favourite

Apartment in Orlando

4.98 out of 5 average rating, 142 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

5–12 Oct

$218 SGD per night

Guest favourite

Apartment in Orlando

4.87 out of 5 average rating, 182 reviews

Amazing Views & Location <1 mile Disney - Sleeps 6

I offer a safe, clean, secure and affordable unit in a well equipped complex that is close to all major attractions that offers peace of mind for my guests. It's a spacious one bedroom, two bath unit with a specular lakefront view at the Blue Heron Beach Resort nestled on the shores of 400 plus acre Lake Bryan, just 1 mile to Disney Springs. This luxurious unit is located on the 12th floor with balcony overlooking the pool and Lake Bryan. This unit sleeps a maximum of 6

14–21 May

$144 SGD per night

Guest favourite

Apartment in Orlando

4.97 out of 5 average rating, 105 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, Amway Arena Concerts and Sporting Events and more!!!

23–30 Apr

$198 SGD per night

Guest favourite

Apartment in Orlando

4.91 out of 5 average rating, 184 reviews

Deluxe Studio:Lakeview, parking, pool

Renovated studio on International Drive in 'The Enclave Hotel and Suites' IMPORTANT: *no early check ins/late check outs, luggage hold/drop off or mail/package delivery option *Please read entire listing/house rules. We give a lot of important information about the buildings, WiFi and distance to main attractions. *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.

31 Aug – 7 Sep

$156 SGD per night

Guest favourite

Apartment in Orlando

4.82 out of 5 average rating, 108 reviews

Designer Orlando Retreat near UCF & Outdoor Space

Free items included: - Free laundry detergent - Coffee kit with delicious toppings - Ultra Fast Wifi and Cable TV - SmartTV w/ Netflix, Disney+, HBO - Premium toiletries and soft towels This condo is quiet, cozy, and located in a quiet neighborhood. Our corner unit allows alot of natural sunlight into the unit. Two bedrooms all have their own private bathrooms. You can enjoy the community pool, basketball, tennis, or go for a nice walk in the nearby trails.

9–16 Jun

$164 SGD per night

Apartment in Orlando

4.88 out of 5 average rating, 109 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.

5–12 Jun

$152 SGD per night

Apartment in Orlando

4.83 out of 5 average rating, 305 reviews

Lakefront Studio apt~ 5 min from Universal Studios

Modern studio, intimate ,relaxing and quiet with spectacular lake views from balcony. Perfectly located for the best possible Orlando vacation experience! It is just off International drive close to Major Attractions, Theme Parks, Dining and Shopping. Located Minutes from Universal Studios ! We offer round-trip SHUTTLE SERVICES to all Parks !Outdoor heated pool , indoor pool and jacuzzi! 24 hour security, FREE PARKING.

7–14 Aug

$212 SGD per night

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Popular amenities for Winter Park apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Guest favourite

Apartment in Kissimmee

4.92 out of 5 average rating, 264 reviews

Beautiful Beach Style Condo minutes from Disney

12–19 Nov

$163 SGD per night

Guest favourite

Apartment in Orlando

4.87 out of 5 average rating, 396 reviews

DELUXE STUDIO NEAR UNIVERSAL/DISNEY/CONVEN. CENTER

25 Sep – 2 Oct

$144 SGD per night

Apartment in Kissimmee

4.79 out of 5 average rating, 153 reviews

Mickey's Retreat

11–18 Jul

$136 SGD per night

Guest favourite

Apartment in Davenport

4.84 out of 5 average rating, 141 reviews

Full Service Gated Resort, Close to Disney & MCO!

12–19 Sep

$156 SGD per night

Guest favourite

Apartment in Kissimmee

4.84 out of 5 average rating, 105 reviews

Orlando Oasis-Refreshed luxe clean Villa by Disney

19–26 Jan

$149 SGD per night

Guest favourite

Apartment in Kissimmee

4.99 out of 5 average rating, 154 reviews

Bright, Airy Home near Disney and Attractions

4–11 Nov

$195 SGD per night

Guest favourite

Apartment in Kissimmee

4.96 out of 5 average rating, 155 reviews

Welcome to our Son Shine condo ....

20–27 Apr

$187 SGD per night

Guest favourite

Apartment in Four Corners

4.99 out of 5 average rating, 148 reviews

Orlando Fun: Minutes to Disney and Margaritaville

23–30 Apr

$143 SGD per night

Pet-friendly apartment rentals

Guest favourite

Apartment in Orlando

4.9 out of 5 average rating, 109 reviews

Amazing Clean Studio near Conventions & Disney

21–28 Aug

$132 SGD per night

Guest favourite

Apartment in Kissimmee

4.84 out of 5 average rating, 250 reviews

Lake View Family Condo Disney Universal Orlando

11–18 Nov

$155 SGD per night

Guest favourite

Apartment in Kissimmee

4.83 out of 5 average rating, 130 reviews

10 mins to Disney-Hot tub-Queen Puffy Lux bed

28 Sep – 5 Oct

$195 SGD per night

Guest favourite

Apartment in Kissimmee

4.9 out of 5 average rating, 203 reviews

Amazing 2 Bed, 2 Bath condo only 10 min to Disney

28 May – 4 Jun

$163 SGD per night

Guest favourite

Apartment in Champions Gate

4.85 out of 5 average rating, 262 reviews

Magical Champions Gate 3/2 Tuscan Penthouse

1–8 Oct

$175 SGD per night

Apartment in Kissimmee

4.83 out of 5 average rating, 170 reviews

Disney Adorable Condo in the heart of it ALL! 1/1

20–27 Feb

$162 SGD per night

Guest favourite

Apartment in Orlando

4.89 out of 5 average rating, 139 reviews

Vista Cay Penthouse Prize

29 May – 5 Jun

$262 SGD per night

Guest favourite

Apartment in Kissimmee

4.86 out of 5 average rating, 263 reviews

Cozy Chic Renovated 3/2 Condo- Near Disney World!

1–8 Jul

$222 SGD per night

Apartment rentals with a pool

Guest favourite

Apartment in Kissimmee

4.93 out of 5 average rating, 176 reviews

Perfect place for your Disney escape

27 Sep – 4 Oct

$145 SGD per night

Apartment in Kissimmee

4.86 out of 5 average rating, 161 reviews

Beautiful Resort-Style Condo with Waterpark!

22–29 Oct

$199 SGD per night

Apartment in Orlando

4.86 out of 5 average rating, 118 reviews

Gorgeous 1 Bed 2 Bath Condo just 1 mile to Disney

25 Jul – 1 Aug

$176 SGD per night

Apartment in Winter Park

4.78 out of 5 average rating, 97 reviews

Stylish Winter Park Flat: Minutes from Park Avenue

21–28 May

$222 SGD per night

Guest favourite

Apartment in Orlando

4.89 out of 5 average rating, 87 reviews

Entire Condo (MCO)

16–23 Jun

$122 SGD per night

Apartment in Orlando

4.82 out of 5 average rating, 85 reviews

Entire Condominium- Luxury Gated Community

17–24 Aug

$130 SGD per night

Apartment in Orlando

4.8 out of 5 average rating, 35 reviews

Business/Family Vacations Apt. by PLZ2 Vacation

27 Apr – 4 May

$163 SGD per night

Guest favourite

Apartment in Kissimmee

4.85 out of 5 average rating, 55 reviews

Stylish Condo 20 mins to Disney/King Bed

6–13 Sep

$133 SGD per night

Quick stats about apartment rentals in Winter Park

Total rentals
10 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
460 reviews
Nightly prices starting at
$54 SGD before taxes and fees

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