
Waterfront vacation rentals in Winter Park
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Winter Park
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

PentHouse Suite with 2X View
Located at the gates of Walt Disney World, this Awesome PentHouse Suite offers easy access to area theme parks, and entertainment venues in the surrounding area, including Walt Disney World, Universal Studios, Sea-world, Legoland + Amazing Restaurants, Shopping and many more. Best of all wonderful views with 2 Large Balcony's, 1 for Sunrise @ East Side and 1 for Sunset @ West side overlooking Disney World with amazing fireworks every night, Enjoy! **Security camera for safety @ Entry door only!

Lakefront,Sanford airport, Boombah, Venue 1902,UCF
The lake front cottage is located on a private estate 1 mile south of Sanford airport, 4 miles to Sanford historic district, and 3 miles from Boombha Sports Complex. This cottage has a Fully equipped kitchen, light bright liv/din area, screened wrap around porch. Perfect spot for your next family vacation or weekend get away. While staying at the cottage you are welcome to enjoy our paddle boards and kayaks. Also catch and release fishing. No pets. Discounts for non-refundable cancellations.

Mills Lakeside
Beautiful over-sized private 1 bedroom cottage, overlooking the lake. We are close to several other lakes and dog friendly parks to explore. Comfort was our number one focus when choosing furniture, and there is even a king sleep number mattress in the bedroom. The kitchen is fully equipped with a dining area, living area, desk/office space, washer, dryer, flat screen TV, wifi, cable TV with HBO, Netflix & Amazon. Light breakfast & snacks. Please note there is an additional charge to use pool.

Chill 4/2, Lakefront, Game Room, Fishing & Hot Tub
The view of the lake from the patio is worth the price of admission! Tastefully decorated home & comfortable beds makes this a can't miss, home away from home! *Centrally Located (Walmart/Publix ~1 mi) *Close to Parks: Universal, Disney (30 min/40 min) *Short Drive to Beaches (1 hr) *UCF/Winter Park very close (5 min/15 min) *Bunk/Game Room w/pool table, Xbox & Full sized Pac-Man Arcade *Hot tub, Fishing, Games, Grill, Comfort *Close enough to do it all, far enough away for peace & quiet

🕶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 Lakeview Oasis - XL Pool & Jacuzzi - Orlando
Welcome to our stunning lakefront resort, where luxury meets tranquility! Dive into our expansive 100,000-gallon pool, enjoying a refreshing swim surrounded by breathtaking views. Inside, our tastefully designed space features midcentury modern amenities ensuring you have everything for a perfect getaway. Each bedroom offers serene views and plush bedding for a restful night’s sleep. Whether you seek adventure or relaxation, this is your ideal getaway. Book now for unforgettable memories!

St. Augustine suite
Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

Hip RetroModern Lakefront Cabana w/ EV Charger
The Kiwi Cabana is a modern euro-style studio that offers the best in location, comfort, and ambiance! Relax with a glass of wine on the patio or dock & enjoy a gorgeous sunset on the lake. Light the fire pit and fire up the grill for a romantic evening. Luxe Queen Murphy Bed. Wifi. Cable. Outdoor Lighting & Sound System. Spacious Leather Sectional. Multiple Coffeemakers. Dishwasher. Microwave. CounterTop Oven. Electric Vehicle Charger at Dedicated Guest Parking Space. STR License #1009857

The Lake House
Welcome to the mid-century Lake House. 370 square feet apartment with a private entrance and original terrazzo floors. Located on a quiet residential street on a small lake, and located within a 5-minute drive to anything you may need! Starbucks and Panera are within walking distance, and dozens of other places to eat. Publix, Walgreens, and Sprouts are just around the corner. A short 10 minute drive to the famous Park Ave, in Downtown Winter Park with shopping and gourmet restaurants.

Nature Unique lake view Tiny Guest studio
Tiny Guest house studio with separate entrance for privacy and amazing Lake view. Unlimited rental of 2 Blue kayaks included during stay!! Walking distace from windixie supermarket, downtown lake Mary, restaurants, shopping centers, entertainment and dunking Donuts. Common areas outside studio are shared. Property is at lake Mary across Country club, close to Sanford, Boombah Sports, Orlando Fl. 30 min to Daytona Beach. Near Wekiva springs. To go to Disney, easy access to I-4 and 4-17.

Beautiful House Completely Remodeled
Forget your worries in this spacious and serene space. Completely remodeled, everything is brand new. You will love to stay at this beautiful house come and see for yourself! Only 10 minutes away from the airport. 15 minutes away from UCF. 20 minutes from SeaWorld and Aquatica. 30 minutes from Universal Studios, Island of Adventure and Volcano Bay. 30 minutes from Disney World. 10 minutes from Lake Nona. 15 minutes from Down Town. 25 minutes to the Outlets. 15 minutes to Kia Center.

Magnificent Lakefront Home•Swim&Relax•Long Stay OK
Water-ski, swim, boat, and fish in the pristine, spring-fed waters of the 310-acre Bear Lake beside this expansive home. Canoe and paddle boards provided! Enjoy the sunset from the swing on the boat dock, watch the sunrise from the screened deck while lounging in the hammock, or spend a lazy afternoon with the family playing board games. The rental is the private half of a duplex, completely separated from the owner's side, with no shared areas. (2 kings, 2 queens, 3.5 baths)
Popular amenities for Winter Park waterfront rentals
Waterfront apartment rentals

LAKE FRONT Apartment w FREE Kayaking/Canoe

Perfect Getaway location Near Universal Parks

BEST Views~2B2B~Universal~Disney

2-Bedroom Renovated Lakeside Condo Near Disney

2 BR Cozi Apartment

Charming Lakefront Apt. Near Disney

Orlando Studio - Near Universal, OCCC and Disney!

Amazing Apartment in Orlando - Kissimmee
Waterfront house rentals

Huge pool & Lakeview home | 5 Min Universal

Paradise pool home /5 Min Universal /13 min Disney

Edgewater lake house Sanford SFB airport Boombah

Waterfront Wizarding Near Universal's Harry Potter

Spectacular Lake View - Game Room- Close to Disney

Relaxing Orlando 4 BR home, pool & water view

Lakeview Sunsets with Loft Escape West of Orlando

LARNE LODGE House with Hot Tub 3 miles to Disney!
Waterfront condo rentals

Lakeside Resort Condo minutes to Disney, Universal

Retro lake Eola 1 Bedroom Condo Thornton park

Disney Area Updated Lakefront Resort Condo 2 POOLS

Modern Lake view Condo 1 mile from Disney

[Lake View, Modern Decor, 1 Mile to Disney!]

Vista Cay Island Breeze, Next to EPIC & OCCC

3171-206 Resort Lake View Disney Universal Orlando

Full-Service Gated Resort, Disney, Universal, MCO!
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ430 | ﺩ.ﺇ430 | ﺩ.ﺇ430 | ﺩ.ﺇ430 | ﺩ.ﺇ430 | ﺩ.ﺇ404 | ﺩ.ﺇ404 | ﺩ.ﺇ404 | ﺩ.ﺇ452 | ﺩ.ﺇ518 | ﺩ.ﺇ521 | ﺩ.ﺇ521 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about waterfront rentals in Winter Park

Total vacation rentals
Explore 10 vacation rentals in Winter Park

Nightly prices starting at
Winter Park vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

Verified guest reviews
Over 880 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Winter Park vacation rentals include wi-fi 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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- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Orange County Convention Center
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
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- ESPN Wide World of Sports
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- Kia Center
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- Reunion Resort Golf Courses - Palmer & Watson
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