Waterfront holiday rentals in Winter Park

4.96 out of 5 average rating, 189 reviews

The expansive lake is showcased during sunset, reflecting vibrant colors in the sky. Surrounding greenery adds a natural touch, while a dock extends into the water, offering a serene view of the landscape. Soft light illuminates the pathway along the lake's edge.

Hotel room in Orlando

PentHouse Suite with 2X View

Located at the gates of Walt Disney World, this Awesome PentHouse Suite offers easy access to area theme parks, and entertainment venues in the surrounding area, including Walt Disney World, Universal Studios, Sea-world, Legoland + Amazing Restaurants, Shopping and many more. Best of all wonderful views with 2 Large Balcony's, 1 for Sunrise @ East Side and 1 for Sunset @ West side overlooking Disney World with amazing fireworks every night, Enjoy! **Security camera for safety @ Entry door only!

5 out of 5 average rating, 111 reviews

Flat in Orlando

Private Rooftop Suite! No resort fees! 5 star

Enjoy a stylish experience at this centrally-located rooftop terrace. Located at the Enclave Suites, this unit features a rooftop terrace with views overlooking Sandy Lake. Recently remodeled, it boasts practical functionality with beautiful design. This unit is everything you need to enjoy a vacation in Orlando. It is centrally located off of International Drive and minutes from Universal Studios, Volcano Bay, SeaWorld, Disney World and much more. Enjoy a luxurious stay without the hefty price.

4.97 out of 5 average rating, 109 reviews

A serene lakeside view is presented, featuring calm waters reflecting a gradient of soft colors during sunset. A wooden dock extends into the water, framed by lush greenery and grasses. The landscape conveys a tranquil setting, inviting moments of reflection in nature.

Home in Winter Garden

Waterfront EPIC views, Dock, wildlife Near Disney

Experience the stunning sunrise views over Lake Apopka from our newly refurbished, elegantly appointed 4-bedroom, 2.5-bath vacation home in Winter Garden, FL. This haven is close to Orlando's Universal Studios 20 min, Disney World 25 min) & shopping (Mall of Millenia, premium outlets 17 min) Modern amenities, spacious layout that promises relaxation and convenience making the perfect home for exploring all local attractions and enjoying Florida's natural beauty. Minutes from City Swimming Pool

Flat in Altamonte Springs

A spacious outdoor area features a pool surrounded by a tiled patio. Comfortable lounge chairs are neatly arranged around the pool, while decorative planters with blooming flowers add a touch of color. The setting is complemented by manicured lawns and a clear sky.

4.96 out of 5 average rating, 333 reviews

St.John suite

Luxurious space with PRIVATE ENTRANCE, 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 lined streets, 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, 104 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

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.

4.94 out of 5 average rating, 127 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.

Cottage in Altamonte Springs

A charming lakefront cottage is viewed from across the water, showcasing its blue exterior. The porch area includes a deck with seating, and two light-colored lounge chairs are positioned on the grassy lawn, surrounded by lush greenery and trees.

4.99 out of 5 average rating, 135 reviews

Incredible Private Lakefront Cottage Retreat

You can fully relax in this adorable lakefront cottage. We're sure you'll enjoy all of the wonderful amenities this peaceful property has to offer. Our incredibly unique cottage is nestled under a large grand oak tree and tucked away behind climbing jasmine vine clad fencing and security gates. Inside, you will find a new remodeled fully stocked kitchen and luxury bathroom. Our cozy cottage has all the comforts of home and more. Reserve your stay today and enjoy this special property.

4.9 out of 5 average rating, 176 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.

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, 315 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

A cozy sleeping area features a spacious bed adorned with a textured blanket and decorative pillows. Warm light is provided by pendant lights above, while vibrant art pieces and greenery enhance the decor against a neutral backdrop.

4.96 out of 5 average rating, 330 reviews

Costa Rica Vibes Free Bikes 12PM Checkout

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.

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.

4.97 out of 5 average rating, 146 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 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.

4.92 out of 5 average rating, 383 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

Popular amenities for waterfront rentals in Winter Park

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.97 out of 5 average rating, 464 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.

Flat in St. Cloud

LAKE FRONT Apartment w FREE Kayaking/Canoe

4.83 out of 5 average rating, 143 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

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.

4.79 out of 5 average rating, 100 reviews

Magical Holiday+Relax+FreeParking

4.95 out of 5 average rating, 123 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, 213 reviews

Lovely one bedroom apartment.

4.88 out of 5 average rating, 164 reviews

A spacious bed with a burgundy coverlet is positioned beneath vibrant yellow walls. Accents include cushions in a mix of patterns. Soft nightstands with warm lamps flank the bed, while colorful artwork adorns the walls, adding character to the inviting space.

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, 129 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, 110 reviews

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

Waterfront house rentals

4.87 out of 5 average rating, 255 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

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, 134 reviews

Quiet Place, convenient to everything!

4.98 out of 5 average rating, 142 reviews

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

4.89 out of 5 average rating, 157 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

4.99 out of 5 average rating, 145 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

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.

4.96 out of 5 average rating, 249 reviews

The Lake House - Next to Universal Studios - NEW ♥️

A serene sunset is captured, displaying a gradient of orange and pink hues reflected on a calm lake surface. Silhouetted trees frame the scene, enhancing the tranquility of the moment as the sky transitions into twilight.

4.92 out of 5 average rating, 220 reviews

Resort like 4/2.5 lake front saltwater pool

4.89 out of 5 average rating, 100 reviews

Two lounge chairs are positioned beside a heated pool, overlooking a serene lake. A pink flamingo pool float rests nearby. The outdoor area includes a large umbrella for shade, creating a peaceful space for relaxation.

Home in Kissimmee

Dreamy Waterside Villa | Heated Pool & Near Disney

Waterfront apartment rentals

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.

4.93 out of 5 average rating, 123 reviews

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

4.73 out of 5 average rating, 342 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.

Apartment in South Eola

Retro lake Eola 1 Bedroom Condo Thornton park

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, 109 reviews

Modern Lake view Condo 1 mile from Disney

The spacious studio features a queen size bed with a dark quilt and white pillows, complemented by a sleek gray sofa bed nearby. A decorative wall with a leafy pattern enhances the ambiance, while large windows allow natural light to fill the space.

4.83 out of 5 average rating, 137 reviews

Studio close to Universal & Epic + free Netflix

The living area features a spacious gray sectional sofa and a wooden coffee table atop a round, textured rug. A large TV is mounted on a media console, and natural light flows through the floor-to-ceiling sliding doors leading to a balcony with lake views.

4.89 out of 5 average rating, 165 reviews

[Lake View, Modern Decor, 1 Mile to Disney!]

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.

4.87 out of 5 average rating, 303 reviews

🕶Your Private Terrace In The Sky🕶 Great Views

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, 469 reviews

Lake-front view at International Drive & Universal

A spacious living area features a large window providing views of the lake, adorned with sheer curtains. Comfortable seating includes a dark blue sofa beside a wooden side table. A dining area, equipped with metal bar stools, complements the modern decor, highlighted by a ceiling fan.