
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.

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.

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!

Tahiti Gilâs Mananui: Disney Poly & Tiki Inspired!
Aloha Adventurers! Welcome to FarĂŠ Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room âstory dwellingâ adventure from the moment you step thru the door! - Kungaloosh!!

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 nightâs sleep. Whether you seek adventure or relaxation, this is your ideal getaway. Book now for unforgettable memories!

Lake Front Home with private Dock on Lake Louisa
Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow cleaning and disinfecting of the house

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

Incredible 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.

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.

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.

Sunset Cottage in Lake Mary, Florida
Located on beautiful Lake Mary, this completely renovated studio sized guest house offers beautiful sunsets over the lake from a private patio. A comfortable queen bed, stylish sitting area and fully stocked kitchenette make for a wonderful stay in the Lake Mary- Sanford area. Minutes from the Sanford airport, close to the Sunrail station and 45 minutes to either Disney World or the beach. Our guest cottage is a perfect place to visit. Please note: The cottage is lakeview only.
Popular amenities for Winter Park waterfront rentals
Waterfront apartment rentals

Gorgeous spot 6 min drive to Universal Studios

Penthouse With EPIC Views

BEST Views~2B2B~Universal~Disney

2-Bedroom Renovated Lakeside Condo Near Disney

2 BR Cozi Apartment

Charming Lakefront Apt. Near Disney

Modern Studio near OCCC | Fast Wi-Fi | Quiet Stay

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

Private 3-bedroom pool & waterfront home

Game Room/HeatedPool/Piano Upscale Waterfront Home

Huge pool & Lakeview home | 5 Min Universal

Waterfront Wizarding Near Universal's Harry Potter

Adorable Downtown Lakeview Home 1105

Hotel style bed House Near Disney

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

Wekiva Riverfront Home with Dock Close to Springs!
Waterfront condo rentals

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

Retro lake Eola 1 Bedroom Condo Thornton park

Disney Area Updated Lakefront Resort Condo 2 POOLS

Private Rooftop Suite! No resort fees!

Waterfront Condo minutes to Disney & Universal

Chic Disney Resort Condo ⢠Pool Access Near Parks

Modern Lake view Condo 1 mile from Disney

2-bedroom condo w/ stunning lake and Disney views
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$24,487 GYD | G$24,487 GYD | G$24,487 GYD | G$24,487 GYD | G$24,487 GYD | G$23,022 GYD | G$23,022 GYD | G$23,022 GYD | G$25,742 GYD | G$29,510 GYD | G$29,719 GYD | G$29,719 GYD |
| 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 G$4,186Â GYD 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 guestsâaveraging 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
Destinations to explore
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- Rentals with a patio Winter Park
- Fitness-friendly rentals Winter Park
- Pet-friendly rentals Winter Park
- Rentals with pools Winter Park
- Rentals with a fire pit Winter Park
- Rentals with a washer and dryer Winter Park
- House rentals Winter Park
- Rentals with lake access Winter Park
- Rentals with outdoor seating Winter Park
- Rentals with a hot tub Winter Park
- Guesthouse rentals Winter Park
- Rentals with a fireplace Winter Park
- Private suite rentals Winter Park
- Condo rentals Winter Park
- Rentals with an EV charger Winter Park
- Apartment rentals Winter Park
- Family-friendly rentals Winter Park
- Waterfront rentals Orange County
- Waterfront rentals Florida
- Waterfront rentals United States
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Magic Kingdom Park
- Universal's Volcano Bay
- Ocean Center
- Orlando / Kissimmee KOA
- Daytona Beach Bandshell
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Daytona International Speedway
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Playalinda Beach
- Disney's Hollywood Studios
- Things to do Winter Park
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- Nature and outdoors Orange County
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- Things to do United States
- Tours United States
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- Art and culture United States
- Entertainment United States
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