Waterfront vacation rentals in Winter Park

4.98 out of 5 average rating, 253 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.

4.92 out of 5 average rating, 163 reviews

A cozy living area features comfortable seating and a flat-screen TV, complemented by light streaming in through white blinds. A well-equipped kitchen is visible in the background, and an inviting bedroom with a king bed is seen alongside a detached private sauna, surrounded by lush greenery.

Cottage in Orlando

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.

4.97 out of 5 average rating, 184 reviews

The exterior of the barn showcases a rustic wooden facade beneath a metal roof. A porch with seating options invites relaxation, while the neatly maintained yard features green grass and landscaping. A driveway leads to a side garage, enhancing the property's charm and accessibility.

Barn in St. Cloud

Rustic Barn Retreat

Experience the rustic elegance of this beautifully remodeled 1,800 sq. ft. barn nestled on a serene 17-acre property. Unwind in the private heated hot tub and soak up the peaceful surroundings. The prime location offers convenient access to major attractions—just a 35-45 min drive west will take you to Disney, Universal, SeaWorld, and gator parks, while a 45-60 min drive east leads you to the breathtaking Atlantic beaches and the Space Coast. Plus, the property is only 40 min from the airport

A spacious outdoor area features a large pool with crystal-clear water, accompanied by a hot tub and a soothing water fountain. Surrounding the pool, a stone patio hosts multiple seating areas beneath a pergola, providing a serene setting for relaxation.

4.97 out of 5 average rating, 103 reviews

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

Guest suite in Altamonte Springs

A serene pool area features a clear blue pool surrounded by elegant tile flooring. Comfortable lounge chairs are arranged around the pool, providing ample space for relaxation. Potted plants add a touch of greenery to the setting, contributing to a calming atmosphere.

4.96 out of 5 average rating, 390 reviews

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

4.91 out of 5 average rating, 146 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, 163 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.

4.95 out of 5 average rating, 168 reviews

The image depicts a calm lake at sunset, with reflections of clouds and colors mirrored in the water. In the foreground, a fishing boat is anchored, positioned near the lake's serene shoreline surrounded by lush greenery.

Home in Longwood

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

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, 182 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.

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, 145 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.

4.93 out of 5 average rating, 408 reviews

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.

Guest suite in Orlando

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

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, 277 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

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, 119 reviews

Perfect Getaway location Near Universal Parks

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, 176 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, 179 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, 106 reviews

2-Bedroom Renovated Lakeside Condo Near Disney

4.8 out of 5 average rating, 311 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

4.95 out of 5 average rating, 108 reviews

The living room is designed with a modern aesthetic, featuring a spacious sectional sofa, a coffee table, and a 65-inch Smart TV mounted on the wall. Large glass doors provide access to the outdoor area, allowing natural light to fill the space.

Apartment in Kissimmee

3171-302 Resort Lake View Disney Universal Orlando

Superhost

A private balcony features a table and four chairs, overlooking a serene lake. The shimmering pool area is visible below, surrounded by lush green trees. Clear blue skies provide a tranquil backdrop to the scenic outdoor space.

4.9 out of 5 average rating, 101 reviews

Apartment in Orlando

4.93 out of 5 average rating, 136 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, 114 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.

4.97 out of 5 average rating, 346 reviews

Game Room/HeatedPool/Piano Upscale Waterfront Home

4.89 out of 5 average rating, 106 reviews

A spacious backyard features a refreshing pool surrounded by a large patio of pavers. Comfortable lounge chairs are positioned nearby, and a covered patio offers shaded seating, creating an inviting space for relaxation and leisure.

Home in Doctor Phillips

Paradise pool home /5 Min Universal /13 min Disney

A grand living area showcases a striking stone wall adorned with an extensive collection of framed artwork. Soft seating is arranged around a fireplace, providing a cozy yet elegant atmosphere. A staircase leads to the upper level, while rich drapery frames the large windows, allowing natural light to flow in.

4.95 out of 5 average rating, 213 reviews

Waterfront Wizarding Near Universal's Harry Potter

4.97 out of 5 average rating, 118 reviews

A living area features a cozy couch with a blue and white design, paired with a wooden coffee table at the center. Bright light filters through the window with white blinds. The kitchen is visible in the background, showcasing wooden cabinets and modern appliances.

Home in Clermont

Adorable Downtown Lakeview Home 1105

4.9 out of 5 average rating, 174 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, 162 reviews

Heated Pool 15 Minutes to Disney PS5 l Switch

4.98 out of 5 average rating, 120 reviews

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

Waterfront condo rentals

4.89 out of 5 average rating, 114 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, 148 reviews

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

The living room features large sliding glass doors that open to the balcony, providing a view of the lake. A contemporary electric fireplace sits beneath a 65-inch smart TV. Comfortable seating includes a sofa, an armchair, and a coffee table, with warm curtains adding a touch of color.

4.96 out of 5 average rating, 119 reviews

Penthouse Lakeview Minutes to Disney/ Universal

4.98 out of 5 average rating, 131 reviews

Disney Area Updated Lake View Orlando Resort Condo

4.91 out of 5 average rating, 171 reviews

Condo in Kissimmee

Chic Disney Resort Condo • Pool Access Near Parks

4.95 out of 5 average rating, 132 reviews

Modern Lake view Condo 1 mile from Disney

4.98 out of 5 average rating, 172 reviews

A winding lazy river pool is surrounded by lush palm trees and tropical landscaping. Water features, including slides and spraying elements, create an engaging atmosphere. Steps lead into the pool, which is framed by natural stone and tile, offering a serene escape in a vibrant setting.

Condo in Kissimmee

Top Floor Condo Lake View near Disney Storey Lake

A bright living space showcases large windows with lake views, allowing natural light to fill the area. Two comfortable sofas and a round coffee table create a cozy seating arrangement. A dining table is visible nearby, along with modern decor and a wall-mounted TV.