Waterfront vacation rentals in Winter Park

4.94 out of 5 average rating, 155 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.

The living room features a grey sofa adorned with decorative pillows, paired with a glass coffee table and a vibrant area rug. The open space leads to a dining area and modern kitchen, highlighted by yellow bar stools at the countertop under soft lighting.

4.86 out of 5 average rating, 333 reviews

BreathtakingView-1BR/2BA-1 Mile to Disney-Sleeps 5

Located 1 mile to Disney Springs in a Gated-Community A NEWLY REFURBISHED Spacious 1-bedroom, 2-bath Condo in Lakefront luxury @ Blue Heron Beach Resort nestled on shores of 400+ acre Lake Bryan, 2 blocks off I4 @ Lake Buena Vista exit. This luxurious condo overlooks the Pool & Lake Bryan. Sleeps 4 It’s all here! The ultimate Walt Disney World vacation right here at your fingertips! From the best of Disney or Work Travel this property offers the perfect environment to spend a lifelong memory

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, 371 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

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, 109 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

4.94 out of 5 average rating, 134 reviews

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.

Home in Orlando

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.

4.91 out of 5 average rating, 190 reviews

The bedroom features a spacious bed dressed in soft blue bedding, complemented by two bedside lamps on wooden tables. Decorative curtains with a water-themed design frame the window, while a subtle area rug adds texture to the room's original terrazzo flooring.

Apartment in Winter Park

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.

4.94 out of 5 average rating, 114 reviews

A well-manicured pathway leads to the studio, surrounded by lush greenery and colorful plants. Visible are large windows framed by white curtains, providing a view of the scenic lake. A patio with a red umbrella and a picnic table is accessible for outdoor relaxation.

Guesthouse in Lake Mary

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.

Guesthouse in Wadeview Park

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.

4.86 out of 5 average rating, 326 reviews

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.

4.97 out of 5 average rating, 157 reviews

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.

Home in Orlando

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 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, 391 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

An outdoor seating area features comfortable couches adorned with colorful cushions. A coffee table sits in the center, surrounded by vibrant area rugs. Decorative lanterns hang overhead, and the backdrop includes lush greenery, creating an inviting space for relaxation and socializing.

Tiny home in Orlando

4.88 out of 5 average rating, 101 reviews

FunTropicalTinyGemUCF

Ready for an unforgettable getaway? Escape to our brand-new Tiny RV House — where fun meets relaxation in a one-of-a-kind space! Proudly a ‘GOLD Guest Favorite’ and ranked in the top 10% of all Orlando Airbnbs. 100% Unique. Features a very comfortable King Bed, WiFi, Smart TV, fireplace, central A/C, and heat. Enjoy stunning lake views front the screened room free of mosquitoes! Cozy, stylish, and packed with charm — come see why guests can’t stop raving!

5 out of 5 average rating, 468 reviews

A backyard oasis is highlighted by a heated spa and pool, illuminated in vibrant blue hues. A multi-level deck features outdoor seating and a colorful pride flag. Lush greenery surrounds the area, creating a secluded and inviting atmosphere.

Guest suite in Orlando

LAKEFRONT STUDIO APARTMENT (private entrance)

This studio apartment is located in the lower level of our home and is perfect for one or two people. It has a private entrance, a king bed, overlooks the pool and the lake with views of downtown Orlando. Please note there is no kitchen, but there is a wetbar with microwave and mini fridge. In addition to the indoor shower, there is also a outdoor shower and a dock with canoe. Please also note the inside ceiling height is lower than average at 6'3”.

Popular amenities for Winter Park waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.96 out of 5 average rating, 472 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

4.84 out of 5 average rating, 153 reviews

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.

Apartment in Orlando

BEST Views~2B2B~Universal~Disney

4.95 out of 5 average rating, 135 reviews

An open living space features a dining area with a dark wood table and chairs. A glass coffee table sits in front of a light-colored sofa. Light wood flooring is observed, complemented by wall art and stylish accents, creating an inviting atmosphere throughout the room.

Apartment in St. Cloud

2 BR Cozi Apartment

4.93 out of 5 average rating, 218 reviews

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.

Apartment in Kissimmee

Lovely one bedroom apartment.

4.96 out of 5 average rating, 147 reviews

A serene view of a calm lake surrounded by well-maintained buildings within a gated community. Two birds fly gracefully over the water, and a fountain can be seen in the distance, adding to the peaceful ambiance of the scene.

Apartment in Kissimmee

WATER View 4BR/Elevator/DISNEY Area

4.88 out of 5 average rating, 166 reviews

Apartment in Orlando

Renovated Studio-Near INT'L Drive and Parks!

4.76 out of 5 average rating, 150 reviews

Apartment in Orlando

29-Universal, International Dr,Convention Center

4.93 out of 5 average rating, 117 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

4.96 out of 5 average rating, 331 reviews

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.

Home in Kissimmee

Game Room/HeatedPool/Piano Upscale Waterfront Home

4.87 out of 5 average rating, 258 reviews

The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.

Home

3 bedroom Villa in Kissimmee

4.96 out of 5 average rating, 110 reviews

The private pool is surrounded by a spacious patio, featuring a gentle curve and inviting turquoise water. A covered dock is visible in the background, with lush greenery and a fence enhancing the outdoor space.

Home in Orlando

Private Pool 4/2 Waterfront Oasis Weekly Discounts

4.99 out of 5 average rating, 157 reviews

An expansive outdoor pool deck is featured, surrounded by lounge seating and shaded areas. A giant outdoor chess set stands nearby, along with a view of the scenic forest and pond. A brightly decorated game area showcases themed decor and entertainment options.

Home in Four Corners

*Luxurious Paradise Mansion: Pool, Spa & Cinema

Superhost

Home in Davenport

4.86 out of 5 average rating, 114 reviews

1157 5BD Dream Home Decoration - Champions Gate

4.99 out of 5 average rating, 151 reviews

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.

Home in Kissimmee

Heated Pool 15 Minutes to Disney PS5 l Switch

4.98 out of 5 average rating, 102 reviews

Home in Kissimmee

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

4.94 out of 5 average rating, 216 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

A spacious studio layout is displayed with a well-equipped kitchen featuring a two-burner induction cooktop and a countertop oven. The living area includes a cozy couch and a media console, with large windows allowing natural light to illuminate the space.

4.9 out of 5 average rating, 244 reviews

Deluxe studio near Epic & Universal, free parking

A spacious bedroom features a large bed topped with a neatly arranged quilt, flanked by two bedside tables with lamps. Natural light filters through a window adorned with sheer curtains, highlighting the soft carpet and accent wall artwork.

4.9 out of 5 average rating, 110 reviews

IS3-205 Lakefront Condo - Close to All Attractions

A bright living area features a cozy gray sofa paired with two stylish yellow chairs. A wooden coffee table sits atop a textured area rug, while large glass doors lead to a balcony that offers views of Lake Bryan.

4.95 out of 5 average rating, 115 reviews

Modern Lake view Condo 1 mile from Disney

4.94 out of 5 average rating, 136 reviews

The master bedroom features a spacious bed with a tufted headboard, complemented by a decorative mirror and framed artwork. Natural light streams in through a large window, revealing views of greenery. A warm color palette and wood accents create a relaxing atmosphere.

Condo in Kissimmee

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

4.92 out of 5 average rating, 199 reviews

A modern living area features a plush blue sectional sofa complemented by two stylish lounge chairs. A light area rug sits under a chic coffee table, while large sliding glass doors provide a view of the outdoors and allow natural light to enhance the space.

Condo in Kissimmee

3171-206 Resort Lake View Disney Universal Orlando

A wooden dock extends over a calm lake, leading to a gazebo with a metal roof. The scene is illuminated by the warm hues of a sunrise, with soft pink and orange clouds reflecting on the water's surface.

5 out of 5 average rating, 123 reviews

2 Miles from Disney, 2 BR. Lake Front, 19Th Floor

4.95 out of 5 average rating, 326 reviews

A serene reflection of colorful townhouses is visible on the calm water of the pond in the foreground. Palm trees line the shore, adding a tropical touch to the scenic landscape under a clear blue sky.

Condo in Kissimmee

Cozy ❤️ Beach Style Condo near Disney & Universal

A dining area on a spacious terrace features a wrought-iron table with seating for six. The table is set with plates, glasses, and utensils, accompanied by a bottle of sparkling wine. A large umbrella provides shade, with distant views of nearby buildings.