Waterfront vacation rentals in Winter Park

4.98 out of 5 average rating, 246 reviews

A screened wrap-around porch offers views of the lake, with sunlight casting striped shadows on the floor. Two lounge chairs are positioned for relaxation, while a colorful playpen is set against the railing. Decorative surfboards are mounted on the walls, enhancing the space's charm.

Cottage in Sanford

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.

Place to stay in Audubon Park

A modern structure with a sloped roof is set amidst lush greenery. The open patio features sleek outdoor seating, providing a comfortable space for relaxation. Large windows allow natural light to fill the interior, while the manicured lawn adds to the serene environment.

4.98 out of 5 average rating, 110 reviews

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

4.9 out of 5 average rating, 100 reviews

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.

4.92 out of 5 average rating, 142 reviews

A spacious outdoor deck is presented with several seating options, including lounge chairs and a dining table. Lush greenery surrounds the area, with a golf course visible in the distance under a bright blue sky scattered with clouds.

Bungalow in Sanford

The Golf-view House (Entire House, King bedroom)

This 2/1.5 house is private, clean, and cozy. The open kitchen features stainless steel appliances and provides all necessary cooking wares. The spacious dining/livingroom area receives enough sunlights through the picture windows. Enjoy beautiful golf course view while sitting at the dining table and/or on the humongous outside deck. There is an outdoor dining area and grill on the deck. The house is within 45 minutes from theme parks (Disney & Universal) and beaches (Daytona/New Smyrna).

A spacious game room features a blue pool table at its center, surrounded by light wooden flooring. To one side, seating options include modern chairs and a couch, with natural light filtering through large windows. The kitchen and dining area are visible in the background.

4.95 out of 5 average rating, 152 reviews

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.

A spacious living area is displayed, featuring a sectional sofa and a large wall-mounted TV. The open kitchen showcases modern appliances and a dining table for six. Natural light floods the space through sliding glass doors that lead to the backyard.

4.96 out of 5 average rating, 175 reviews

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.

Guest suite in Altamonte Springs

A bright living area features large windows with light beige curtains, allowing natural light to fill the space. A vintage dresser is positioned next to a blue upholstered chair adorned with decorative pillows. Warm wooden flooring and an area rug add to the room's cozy atmosphere.

4.97 out of 5 average rating, 349 reviews

St. Hemingway Suite

Very tranquil Romantic Suites with views and access to large lake. PRIVATE ENTRANCE and private bathroom. Amenities include, private dock, pool, large manicured lawns, private parking, breakfast kitchenette and much more. Close to theme parks and beaches. Ample shopping and award winning restaurants very nearby. Peaceful setting to read, do Yoga, enjoy quiet moments by the lake, watch the boats sail by or watch the sun rise. Peace and tranquility at its best. We welcome you

5 out of 5 average rating, 105 reviews

A dining table is set with a tray of assorted cheeses, fruits, and spreads, while glasses sit ready for drinks. Large glass doors reveal views of Bear Lake and a deck with seating, enhancing the inviting ambiance.

Home in Apopka

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)

Home in Altamonte Springs

A spacious living area features a large leather sectional sofa facing a stone fireplace. Natural light floods the room through skylights and glass doors that lead to the screened-in pool. An adjacent dining area is visible, showcasing a wooden table with chairs.

4.82 out of 5 average rating, 142 reviews

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.

Guest suite in Lake Underhill

A private outdoor area is showcased, featuring a sparkling pool accompanied by a hot tub. Lush greenery and colorful plants surround the space, while comfortable seating options, including bright blue chairs, invite relaxation. A pergola provides shade, enhancing the tranquil atmosphere.

4.93 out of 5 average rating, 404 reviews

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

Superhost

A screened patio features a clear view of the serene lake, with sunlight reflecting off the water. Lounge chairs are positioned around the pool, designed for relaxation. Soft greenery and a wooden deck enhance the backdrop, creating an inviting outdoor space.

4.85 out of 5 average rating, 102 reviews

Lake House - Downtown Orlando

Welcome to lakefront paradise! This charming residence in Downtown Orlando, offers an oasis of tranquility and comfort for the whole family. Located in a picturesque lakefront setting, this home is the perfect place to enjoy the serenity of the water and create unforgettable memories. With spacious indoor and outdoor areas, there's plenty of room to relax and entertain. - Pool Heather Available upon request(extra charge due to electricity)

A modern living area features two comfortable sofas, a wooden coffee table, and a vibrant green plant. A sleek television is mounted on the wall, while the open kitchen area showcases contemporary cabinetry and a light backsplash. Natural light flows in through large windows.

4.95 out of 5 average rating, 273 reviews

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.

Popular amenities for Winter Park waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.97 out of 5 average rating, 490 reviews

A silhouette of a crane stands at the lake's edge against a vibrant sunset. The sun casts a warm orange and yellow glow over the water, creating a peaceful backdrop. The surrounding foliage is subtly outlined by the light reflecting on the surface.

Apartment in St. Cloud

LAKE FRONT Apartment w FREE Kayaking/Canoe

The outdoor area features a large swimming pool surrounded by palm trees and lounge chairs. A spacious building is visible in the background, complemented by a clear blue sky. Well-maintained greenery adds to the welcoming environment.

4.98 out of 5 average rating, 115 reviews

Perfect Getaway location Near Universal Parks

4.87 out of 5 average rating, 104 reviews

Apartment in Kissimmee

2 Bd/ 2 Ba Sleeps 6! Storey Lake (3191-405)

A private terrace is presented with ample lounge chairs facing a scenic waterfront view. Lush greenery surrounds the area, and a bright blue sky is visible above, enhancing the open atmosphere. The cityscape with buildings is visible in the distance.

4.85 out of 5 average rating, 169 reviews

BEST Views~2B2B~Universal~Disney

A comfortable living area is showcased with modern furnishings, including a sectional sofa adorned with colorful accent pillows. A coffee table is positioned on a patterned rug, while large glass doors lead to a balcony offering views of the surrounding area. A wall-mounted television is available for entertainment.

4.8 out of 5 average rating, 177 reviews

Top-Floor Lakeview Condo at Vista Cay Resort

A private balcony is showcased with a round table and two woven chairs, providing a serene view of the lake and surrounding landscape. Soft morning light reflects on the water, while a small potted plant adds a touch of greenery to the setting.

4.97 out of 5 average rating, 104 reviews

2-Bedroom Renovated Lakeside Condo Near Disney

4.81 out of 5 average rating, 305 reviews

The bedroom features a spacious bed adorned with soft pillows and a textured throw blanket. Flanking nightstands hold stylish lamps, providing gentle lighting. A framed landscape image above the bed complements the neutral color scheme, and doorways to additional spaces are visible in the background.

Apartment in Clermont

Charming Lakefront Apt. Near Disney

4.94 out of 5 average rating, 129 reviews

The modern kitchen is equipped with stainless steel appliances, including a large refrigerator, microwave, and oven. A granite countertop offers ample workspace, complemented by sleek cabinets. Pendant lights hang above the island, and a dining area is visible in the background.

Apartment in Kissimmee

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

Waterfront house rentals

Superhost

A single-story home is viewed from the street, featuring a covered front entrance and a large driveway. Lush green grass surrounds the property, with palm trees and other foliage enhancing the front yard. The home is enclosed by a privacy fence.

Home in Montverde

4.81 out of 5 average rating, 111 reviews

Private 3-bedroom pool & waterfront home

An inviting pool area is framed by a screened enclosure, revealing beautiful water views at sunset. Soft lighting enhances the relaxing atmosphere, with lounge seating positioned nearby for comfort. The tranquil setting is ideal for unwinding and enjoying outdoor moments by the pool.

4.96 out of 5 average rating, 337 reviews

Game Room/HeatedPool/Piano Upscale Waterfront Home

4.93 out of 5 average rating, 105 reviews

Lakeside Paradise, 15 min Disney + Saltwater Pool

4.98 out of 5 average rating, 159 reviews

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

4.89 out of 5 average rating, 169 reviews

A scenic view overlooking Starke Lake is presented, featuring a spacious deck with railing. A tranquil pool is visible in the foreground, while vibrant clouds reflect the colors of a sunset in the background, enhancing the natural beauty of the surroundings.

Home in Ocoee

Lakeview Sunsets with Loft Escape West of Orlando

A private heated pool is set within a screened enclosure, surrounded by a patio area. Two blue chairs and a white lounge chair are positioned nearby, with lush greenery visible beyond the pool. The clear water reflects the sky, creating a serene atmosphere.

4.99 out of 5 average rating, 159 reviews

Heated Pool 15 Minutes to Disney PS5 l Switch

4.98 out of 5 average rating, 113 reviews

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

4.94 out of 5 average rating, 222 reviews

Two wooden cabins are positioned under tall trees, reflecting on the calm water's surface. A small seating area with bright blue chairs and a fire pit is situated on the grassy shore, providing a relaxed outdoor space, while the surrounding nature complements the serene setting.

Home in Clermont

Lake Front Home with private Dock on Lake Louisa

Waterfront condo rentals

4.89 out of 5 average rating, 109 reviews

Lakefront Studio | Universal Views | Near I-Drive

An aerial view of the clubhouse area is displayed, featuring a large pool surrounded by lounge chairs. Palm trees provide greenery around the poolside, while guests can be seen enjoying the water. The architecture of the clubhouse complements the inviting outdoor space.

4.92 out of 5 average rating, 138 reviews

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

4.74 out of 5 average rating, 359 reviews

Downtown Orlando is depicted with its skyline in the background, framed by a tranquil lake. Three fountains create gentle sprays in the water, reflecting the vibrant blue sky. Lush trees line the water's edge, adding greenery to the urban landscape.

Condo in South Eola

Retro lake Eola 1 Bedroom Condo Thornton park

A balcony view showcases a round table and two chairs facing the expansive lake. The serene water reflects the clear blue sky, while the railing provides safety and openness to the picturesque landscape.

4.98 out of 5 average rating, 128 reviews

Disney Area Updated Lakefront Resort Condo 2 POOLS

4.95 out of 5 average rating, 129 reviews

Modern Lake view Condo 1 mile from Disney

A spacious living area features a comfortable sectional sofa and a coffee table atop a textured rug. Light blue walls enhance the bright atmosphere, while artwork adorns the walls. The open kitchen includes wooden cabinetry and modern appliances, with seating available at the countertop.

4.96 out of 5 average rating, 101 reviews

Renovated Condo 2 miles away from Disney Lake view

A balcony view captures a vibrant sunset over Lake Bryan, with hues of pink and orange reflected on the water. Outdoor seating includes two chairs and a small round table, inviting relaxation while enjoying the scenic surroundings.

4.98 out of 5 average rating, 249 reviews

Lakefront Resort Condo near Disney and Universal

A welcoming living area features a white sofa and a dark coffee table set against light walls. Two lamps provide soft illumination, while a sleek chair adds comfort. Natural light enters through a large window dressed with sheer curtains, enhancing the tranquil atmosphere.