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

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.

The Boat House on Lake Dora - Downtown Waterfront
WATERFRONT! The Boat House is an 800sf private residence built directly over Lake Dora offering panoramic lakefront views. Located on Mount Dora's Famous Boat House Row, right in the heart of downtown Mount Dora, where you can roll out of bed and walk a few steps to one of the quaint coffee shops. The Boat House was once a tin boat shed with floors open to the water and housed two boats. Today, you will find warm, cozy furnishings, comfortable beds, a quiet location and sunsets every evening!

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

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

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.

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.

Quiet Place, convenient to everything!
Spacious home in a very quiet residential neighborhood. Perfect home away from home for your special getaway. Vacations, business trips, wedding groups, graduations have all been hosted in the past, and everyone had a great time. There's significant value in having your own quiet place and multiple rooms in a family-friendly setting. DO NOT BOOK MY QUIET PLACE IF YOUR PLAN INCLUDES ANY LARGE GATHERING WHICH MIGHT IMPACT MY HOME OR NEIGHBORHOOD. YOUR RESPECT IS EXPECTED.

Downtown Orlando Garden Retreat
This space is a mother-in-law suite, completely private from the main house, accessible through a private entrance outside and entering through the garage. THIS IS NOT THE ENTIRE HOUSE! There is a queen size bed... perfect for a couples getaway! It is conveniently located about 15 min. from OIA and 5 min. from downtown Orlando. There is a beautiful pool and hot tub with stunning sunset views of across the lake... so peaceful and you feel like you are in a resort

The Lake House - Next to Universal Studios - NEW ♥️
Luxurious, modern and completely remodeled single-family home with lake access in the prestigious Doctor Phillips neighborhood. Centrally located hops away from all Orlando has to offer, 1.1 miles (3 minutes) from Universal Studios Theme Parks, 9.5 miles to Disney World and 5 miles to Seaworld Orlando. No other Airbnb offers this upscale living space with stunning outdoor area to kick back and enjoy after a long day at the parks.

Retro lake Eola 1 Bedroom Condo Thornton park
Rental agreement needs to be e-signed before check in & ID submitted for legality. Info will not be shared. Check in information will not be shared unless rental agreement is signed and valid ID submitted. Parking: There is 1 designated spot Affordable, no-frills stay in an amazing location. Clean, simple, and budget-friendly — perfect if you value location over luxury. Please be respectful owner lives on property.
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

Top-Floor Lakeview Condo at Vista Cay Resort

2-Bedroom Renovated Lakeside Condo Near Disney

3171-302 Resort Lake View Disney Universal Orlando

Apartment in Orlando

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

Private 3-bedroom pool & waterfront home

Orlando Pool Home • 10m Airport • 25m Disney

Game Room/HeatedPool/Piano Upscale Waterfront Home

3 bedroom Villa in Kissimmee

Waterfront Wizarding Near Universal's Harry Potter

Magnificent Lakefront Home•Swim&Relax•Long Stay OK

Disney Villa w/ Priv Pool & Lake View-12 Mi parks!

Lake Front Home with private Dock on Lake Louisa
Waterfront condo rentals

Lakefront Studio | Universal Views | Near I-Drive

Serene 2BR Escape Near Universal w/Private Terrace

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

Penthouse Lakeview Minutes to Disney/ Universal

Disney Area Updated Lake View Orlando Resort Condo

Waterfront Condo minutes to Disney & Universal

Luxury Lake View Near Convention Center, Universal

Modern Lake view Condo 1 mile from Disney
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 $28 CAD per night before taxes and fees

Verified guest reviews
Over 890 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Winter Park vacation rentals include wifi 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
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