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.

4.93 out of 5 average rating, 193 reviews

A collage of images showcases the private cottage's inviting interior and outdoor amenities. The cozy bedroom features a spacious bed, the pool area is lined with lounge chairs, and the game room displays a pool table and bar. The kitchen is fully equipped for convenience.

Cottage in Orlando

Mills Cottage

Beautiful private upstairs cottage with deck overlooking the lake. It’s near other lakes and dog friendly parks are close. Comfort was the number one reason when choosing furniture and mattresses. Kitchen fully equipped: coffee maker, toaster, microwave, cook top oven, refrigerator, washer/dryer, iron & flat screen TV. Wifi, cable tv, Amazon & Netflix. A dedicated professional work space and desk. Includes light breakfast and snacks. Please note there is an additional charge to use the pool.

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, 104 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

The exterior of a single-story home is depicted, featuring a neatly landscaped front yard with green grass and decorative plants. A driveway accommodates a vehicle, while a garage door is visibly closed. The entrance is framed by a small porch and an arching window above the door.

4.8 out of 5 average rating, 152 reviews

Private Home w/ Pool/3 Bd 2 Bath/Close to Disney

The private home is in the Wellington sub-division in Southchase, Orlando, close to the intersection of SR417 (Greeneway)/Orange Blossom Trail and the Florida Turnpike. It is therefore only minutes to the Walt Disney World, Universal Studios and Sea World theme parks plus some of the world’s best golf courses. There are supermarkets and dining (both formal and informal) nearby. We have a Super Target and a Costco within 2 mile radius. Everything you could possibly need really is close at hand.

4.95 out of 5 average rating, 124 reviews

The exterior of the house showcases a striking blend of wood and stone finishes, featuring large windows that illuminate the interior. An expansive, clear blue pool reflects the sky, with a bridge extending over the water leading to the main entrance.

Villa in Orlando

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

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

4.84 out of 5 average rating, 182 reviews

Huge pool & Lakeview home | 5 Min Universal

Welcome to your ideal vacation retreat! This spacious and cozy lakefront pool house offers everything you need for a memorable family getaway. Perfectly designed for unforgettable trips with 4 BD and 2 BTH, there's plenty of room for everyone to relax. Located just minutes from Universal, Disney and SeaWorld, this house offers the perfect blend of convenience and tranquility. After a day of adventures, return to your serene lakeside retreat and create lasting memories with your loved ones.

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, 164 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

4.85 out of 5 average rating, 346 reviews

An outdoor patio area is furnished with a seating set featuring turquoise cushions, under a shaded pergola. A private pool reflects the blue sky, and a built-in grill is positioned nearby, enhancing the inviting atmosphere for relaxation and outdoor dining.

Guesthouse in Orlando

Couples Oasis *Heated Pool* and Lake View

Have a romantic getaway in this SODO Couples Oasis Retreat with private pool or come work alone in this peaceful oasis. Perfect for couples or the busy profesional who want privacy and quiet with lake view while relaxing by the pool. Centrally located in SODO by downtown Orlando. Close to everything. Walk to great nearby eating places. Love ice cream Kelly’s Hand Made ice cream is a 5 minute walk from the house. *Heated Pool* available for $20 fee for first day and $10 every extra day.

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, 183 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.

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

Popular amenities for Winter Park waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

A scenic view overlooks a serene lake, framed by lush greenery and tall palm trees. The image captures buildings in the distance, with the reflection of structures on the water's surface. A swimming pool area is visible, surrounded by well-maintained landscaping.

4.9 out of 5 average rating, 166 reviews

18 - Near Universal & Lake View

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 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, 107 reviews

2-Bedroom Renovated Lakeside Condo Near Disney

Apartment in Buenaventura Lakes

A well-lit bedroom features a spacious bed with a white quilted cover and decorative pillows. A round mirror is mounted above a side table, complemented by wall art. The room is connected to another area visible through an open door.

4.93 out of 5 average rating, 246 reviews

Lovely one bedroom apartment.

4.8 out of 5 average rating, 312 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

4.87 out of 5 average rating, 148 reviews

A large resort-style pool, shaped like a Mickey Mouse head, is surrounded by palm trees and lounge chairs. Guests are seen relaxing on sun loungers and enjoying the water, with umbrellas providing shade in certain areas. Additional smaller pools are visible nearby.

Apartment in Kissimmee

Amazing Apartment in Orlando - Kissimmee

4.75 out of 5 average rating, 155 reviews

29-Universal, International Dr,Convention Center

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

Waterfront house rentals

4.77 out of 5 average rating, 115 reviews

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

Private 3-bedroom pool & waterfront home

4.89 out of 5 average rating, 107 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

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

A screened-in pool area features sun loungers and a view of a serene lake. The brightly themed kids' bedroom showcases a Toy Story design with two beds, colorful accents, and vibrant wall art. Another room with two twin beds is decorated in soft pink tones, enhancing its cozy feel.

4.83 out of 5 average rating, 149 reviews

Amazing 8Bdrms-5Bath/Game room/Pool

4.98 out of 5 average rating, 171 reviews

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

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, 215 reviews

Waterfront Wizarding Near Universal's Harry Potter

4.88 out of 5 average rating, 104 reviews

Key West Themed Lakefront Oasis with Sailboat

4.91 out of 5 average rating, 209 reviews

Do you Wanna Know Why We’re Among Guest Favorites?

Waterfront condo rentals

A bright living area features soft blue seating arrangements arranged around a wooden coffee table. Sliding glass doors provide access to a balcony with lake views. Neutral wall colors and tiled flooring enhance the spacious feel, while natural light illuminates the space.

4.93 out of 5 average rating, 148 reviews

20th-Floor Lake View•Disney Fireworks•Resort Pool

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, 149 reviews

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

A private balcony features red lounge chairs positioned beside a glass-topped table. Lush greenery and palm trees provide a tropical backdrop, while fluffy clouds drift across a bright blue sky, enhancing the peaceful outdoor space.

4.75 out of 5 average rating, 102 reviews

3BR Condo w Resort Perks near Epic Universe!

4.98 out of 5 average rating, 131 reviews

Disney Area Updated Lake View Orlando Resort Condo

A spacious living area features a comfortable sectional sofa facing a modern coffee table. Bar stool seating surrounds the kitchen island, with stainless steel appliances visible in the background. Soft lighting and a nautical-themed artwork enhance the room's welcoming ambiance.

4.88 out of 5 average rating, 307 reviews

Spacious 1King/2Bath w/stunning lake view

4.91 out of 5 average rating, 173 reviews

Condo in Kissimmee

Chic Disney Resort Condo • Pool Access Near Parks

4.95 out of 5 average rating, 133 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.