
Waterfront holiday rentals in Winter Park
Find and book unique waterfront accommodation on Airbnb
Quick stats about waterfront rentals in Winter Park

Total holiday rentals
Explore 10 holiday rentals in Winter Park

Nightly prices starting at
Winter Park holiday rentals start at $28 AUD per night before taxes and fees

Verified guest reviews
Over 830 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Winter Park holiday 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
Top-rated waterfront accommodation in Winter Park
Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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

Unique Spacious Home w/ Pool near Downtown Orlando
Nestled on a quiet street, 15 mins from Downtown Orlando. This home has a massive pool, hot tub, water fountain, real outdoor and indoor fire place, outdoor patio area w/seating. The Kitchen is equipped with everything you need to make delicious meals, and there are two living areas to provide ample space for relaxation. There is also a designated office area to take work calls. ☀ College Park – 10 mins ☀ Downtown Orlando – 15 mins ☀ Universal Studios – 28 mins ☀ Walt Disney World – 34 mins

Recharging Lakeview Oasis w/Pool centrally located
Fall in love w/ our peaceful home w/ incredible backyard & pool overlooking Lake Gandy! Experience the tranquility of this safe, residential area. New furnishings for your comfort, cozy living room w/ an 85" Smart TV, comfortable bedrooms, laundry room & fully-equipped kitchen for a nice meal. Have fun at our spacious backyard, great for entertainment, bbq's & fire pit s’mores nights! Enjoy delicious organic fruit in the yard! Only 25min away from amusement parks & MCO! Superb for long stays!

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

Lakefront Home•screened deck, dock•Long Stays 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 guest suite is the private half of a duplex, completely separated from the owner's side with no shared areas. (2 kings, 2 queens, 2 futons, 3.5 baths)

Charming Private Lakefront Cottage Retreat
You can fully relax in this adorable lakefront cottage. We're sure you'll enjoy all of the wonderful amenities this peaceful property has to offer. Our incredibly unique cottage is nestled under a large grand oak tree and tucked away behind climbing jasmine vine clad fencing and security gates. Inside, you will find a new remodeled fully stocked kitchen and luxury bathroom. Our cozy cottage has all the comforts of home and more. Reserve your stay today and enjoy this special property.

Lakefront Hot Tub Retreat | Sunset View | Near UCF
Guest suite on private property overlooking beautiful Lake. just 10 min from UCF and 15 minutes to downtown Orlando. Disney is 34 miles while Universal is only 15 miles from the house. This cozy guest suite includes, a private parking spot, luxury rainfall shower, Comfortable Queen size bed, Smart TV, full size refrigerator, Keurig coffee maker, and washer and dryer. The back patio overlooking the lake makes it the perfect spot to watch the sunset while sitting in your private hot tub.

Lake House Retreat w/ Firepit - Centrally Located
Our cozy lakefront retreat in the heart of Orlando boasts a fenced-in backyard with stunning lake views. Relax around the fire pit/wood-burning grill or enjoy a game of corn hole or ping pong on the porch. With a pool table in our game room and comfortable sleeping arrangements for up to 8 guests, this is the perfect place to relax and unwind. Located just minutes from downtown, Disney World, Universal Studios, and the airport, this is an ideal spot to experience all the area has to offer.

Key West Themed Lakefront Oasis with Sailboat
Please read the entire description before booking (including "policies and rules"). This is the lower half of a large lakehouse. Enjoy a resort-like experience with a private pool, heated spa, and stunning sunsets. With a fun Key West theme, it comfortably sleeps your group and features a separate entrance for complete privacy. Enjoy an outdoor kitchen, fire pit, and even a sailboat for a unique stay. Perfect for families seeking a memorable getaway. Kayaks are included for you to explore.

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.

Pvt Fishing lk , Pets,Nature, Pool,garage
No HOA. Private 20 acre lake property, with fishing boats and trolling motors, canoes , peaceful boardwalk / dock. Large extra parking for trailers or work trucks. Fishing gear / poles. 2 car garage for safely storing whatever you bring. Fishing gear, tools, bikes, Harley's. Located near Seminole Trail, parks, sun-rail station. 45-60 min from the beach or the attractions DISNEY, UNIVERSAL STUDIOS, close to Lake Mary, Sanford, Wekiva Springs, Daytona 500, Bike week, 20 min from Boombah

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.
Popular amenities for Winter Park waterfront rentals
Waterfront apartment accommodation

Lake Eola Thornton Park Studio with balcony

BEST Views~2B2B~Universal~Disney

The Johnson’s Apartments / Unit A

Penthouse With Epic Views

UCF home

Top-Floor Lakeview Condo at Vista Cay Resort

Serenity Lake: Spacious & comfy 3BR/2BA Apartment

3161-405 Resort Lake View Disney Universal Orlando
Waterfront house rentals

Cheerful 5-bedroom POOL Home, Next to Universal

Paradise pool home /5 Min Universal /13 min Disney

Huge pool & Lakeview home | 5 Min Universal

Wekiva Riverfront Home with Dock Close to Springs!

Lake Front Home with private Dock on Lake Louisa

Lakefront home near Disney/Beach

Alder wood Lake house near SFB Airport Boombah

Lakeview Sunsets with Loft Escape West of Orlando
Waterfront condo accommodation

Lakefront Resort Studio -5 min to Universal

Location,Location 3bd 2bth near parks conv.ct/Int.

King-Size Townhouse – Minutes to Universal Studios

Penthouse Lakeview Minutes to Disney/ Universal

210 - Disney, Epic Universal, Convention Center

Retro lake Eola 1 Bedroom Condo Thornton park

3BR Condo w Resort Perks near Epic Universe!

Modern Lake view Condo 1 mile from Disney
Destinations to explore
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- Waterfront rentals Orange County
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- Walt Disney World Resort
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- Disney Springs
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- SeaWorld Orlando
- Orange County Convention Center
- Orlando / Kissimmee KOA
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- Epcot
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- Kia Center
- Camping World Stadium
- Disney's Animal Kingdom Theme Park
- University of Central Florida
- Discovery Cove
- Reunion Resort Golf Courses - Palmer & Watson
- Tinker Field
- Old Town
- LEGOLAND Florida Resort
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- ChampionsGate Golf Club
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