Waterfront holiday rentals in Winter Park

4.94 out of 5 average rating, 187 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.

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, 369 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, 108 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

4.91 out of 5 average rating, 189 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.

Flat 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, 109 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.

Guest house 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.

Guest house 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, 325 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.

Tiny home in Baldwin Park

4.96 out of 5 average rating, 343 reviews

Lake View From Bed | Romantic Cabin

Romantic lakefront cabin with Costa Rica vibes in Orlando. Wake to sunrise views from your heated king bed. Sip Cuban espresso in the garden, walk or bike to Baldwin, Winter Park & Downtown or explore The Cady Way Trail. Enjoy a couple’s rain shower, grill, fire pit, and hammock. Guests love the peaceful setting, artful touches, and location minutes from the airport, arena & trails. Perfect for anniversaries, solo stays, and creative escapes. ⚠️Sorry - there is no lake DOCK access.

4.97 out of 5 average rating, 154 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, 390 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

4.9 out of 5 average rating, 99 reviews

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

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, 467 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”.

4.89 out of 5 average rating, 158 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

We are proud to announce No Smoking on premises property. This Duplex A Lake house overlooks Starke Lake in Central Florida. Great fishing, magnificent sunsets and Disney fireworks every night . Close to Disney 19 miles & 12 miles to Universal & 14 miles to Downtown Orlando. Other activities include air boating, Cape Cape Canaveral and centrally located just 1 hour from ocean or gulf. Please NO SMOKING on premises.

Popular amenities for waterfront rentals in Winter Park

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.9 out of 5 average rating, 159 reviews

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.

Flat in Orlando

18 - Near Universal & Lake View

4.84 out of 5 average rating, 152 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.

Flat in Orlando

BEST Views~2B2B~Universal~Disney

Superhost

Aerial view of a resort-style pool area, featuring winding lazy river and colorful waterslides. Surrounding palm trees and lounge chairs enhance the tropical ambiance. The nearby lake provides a scenic backdrop, while various guests can be seen enjoying the water attractions.

4.78 out of 5 average rating, 104 reviews

Lazy River+FreeParking+Tikibar

4.95 out of 5 average rating, 131 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.

Flat in St. Cloud

2 BR Cozi Apartment

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, 217 reviews

Lovely one bedroom apartment.

4.88 out of 5 average rating, 166 reviews

Flat in Orlando

Renovated Studio-Near INT'L Drive and Parks!

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.

4.91 out of 5 average rating, 133 reviews

Amazing Apartment in Orlando - Kissimmee

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.

4.93 out of 5 average rating, 115 reviews

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

Waterfront house rentals

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

4.88 out of 5 average rating, 121 reviews

A serene view of Lake Ada at sunset is captured, showcasing a wooden dock extending over the calm water. Silhouettes of trees line the shore, and a hammock is positioned in the foreground, inviting relaxation amidst the tranquil setting.

Home in Sanford

Edgewater lake house Sanford SFB airport Boombah

4.94 out of 5 average rating, 155 reviews

The living space features a large window allowing natural light to fill the room, showcasing a comfortable bed with an elegant coverlet. A game table and a full-sized pool table with cues are visible, alongside a modern kitchen area equipped with appliances.

Home in Oviedo

Chill 4/2, Lakefront, Game Room, Fishing & Hot Tub

4.99 out of 5 average rating, 150 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, 100 reviews

Home in Kissimmee

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

Superhost

Home in Kissimmee

4.85 out of 5 average rating, 176 reviews

#2613 LakeFront Priv Spa Resort Disney Universal

4.93 out of 5 average rating, 215 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

Superhost

A serene sunset reflects on the tranquil surface of a lake, with vibrant hues of orange, pink, and purple swirling in the sky. Soft ripples create gentle patterns on the water, enhancing the peaceful ambiance of the natural setting.

Home in Orlando

4.81 out of 5 average rating, 329 reviews

Unique lakefront property 6 acres!

Waterfront apartment rentals

4.95 out of 5 average rating, 191 reviews

Apartment in Kissimmee

3161-305 Resort Lake View Disney Universal Orlando

4.91 out of 5 average rating, 154 reviews

A modern living room features a light-toned sofa facing a wall-mounted television displaying tranquil landscape imagery. Soft blue LED lighting enhances the space, while a stylish area rug with geometric patterns adds texture. A glimpse of the kitchen can be seen in the background.

Apartment in Kissimmee

Chic Disney Resort Condo • Pool Access Near Parks

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

4.95 out of 5 average rating, 111 reviews

A Pirates of the Caribbean themed bedroom is presented with two twin beds, featuring bedding adorned with nautical maps. The wall is decorated with a large mural of a pirate skull, and a bedside lamp provides soft lighting. Dark curtains frame a window.

Apartment in Davenport

Themed Resort Condo-Pool | Spa | Beach | 1st Floor

4.94 out of 5 average rating, 135 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.

Apartment in Kissimmee

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

A spacious heated swimming pool is surrounded by palm trees, offering a tropical atmosphere. Lounge chairs with umbrellas line the pool area, providing ample seating for relaxation. The pool's clear blue water reflects the blue sky, enhancing a calm and inviting environment.

4.92 out of 5 average rating, 185 reviews

Spacious+LakeView 3b2b w/Pool&Shuttle to Parks!

The image shows the exterior view of a multi-story condominium building, showcasing several balconies and large windows. Lush palm trees surround the property, and two outdoor swimming pools are visible in the foreground, adding to the community's appeal.

4.73 out of 5 average rating, 476 reviews

Lake-front view at International Drive & 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.