Waterfront holiday rentals in Winter Park

5 out of 5 average rating, 113 reviews

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.

4.94 out of 5 average rating, 150 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.

A serene patio space is presented, featuring a private pool with a smooth surface and relaxing lounge items beside it. The view extends over the lake, framed by trees and a colorful sunset sky in the background, enhancing the peaceful environment.

4.89 out of 5 average rating, 186 reviews

*Lakefront Pool Home *paddleboard*kayak*game room*

This house is a lakefront paradise with a private pool, Paddleboards, Kayaks, a Game room, a King bed in the primary, 70 inch TV, Fast WIFI, Coffee Bar with espresso and cappuccino, body jets and rain head shower, 16-foot kitchen island, 42-inch cabinets, travertine floors, gorgeous granite counters, 7 mi to the airport, 5 mi to Downtown, 20 mi to Disney, 14 mi to Universal, 55 mi to Cocoa Beach. 14 mi to the convention center. The house has a doorbell camera and camera on back left corner.

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, 336 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, 107 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.

4.95 out of 5 average rating, 128 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, 137 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, 178 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.

4.95 out of 5 average rating, 102 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.

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, 149 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.

4.97 out of 5 average rating, 124 reviews

A serene view of Lake Mary is framed by a large tree and a white post. The sky transitions into vibrant hues as the sun sets, reflecting softly on the water's surface. A lamp illuminates the foreground, enhancing the peaceful lakeside atmosphere.

Guest house in Lake Mary

Sunset Cottage in Lake Mary, Florida

Located on beautiful Lake Mary, this completely renovated studio sized guest house offers beautiful sunsets over the lake from a private patio. A comfortable queen bed, stylish sitting area and fully stocked kitchenette make for a wonderful stay in the Lake Mary- Sanford area. Minutes from the Sanford airport, close to the Sunrail station and 45 minutes to either Disney World or the beach. Our guest cottage is a perfect place to visit. Please note: The cottage is lakeview only.

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, 385 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

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, 159 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.

4.83 out of 5 average rating, 146 reviews

BEST Views~2B2B~Universal~Disney

4.79 out of 5 average rating, 101 reviews

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.

Flat in Kissimmee

Magical Holiday+Relax+FreeParking

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, 163 reviews

A Lake View Top Floor Condo! Sparkling & Modern

4.94 out of 5 average rating, 126 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

4.93 out of 5 average rating, 216 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.

Flat in Kissimmee

Lovely one bedroom apartment.

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.

4.88 out of 5 average rating, 164 reviews

Renovated Studio-Near INT'L Drive and Parks!

4.93 out of 5 average rating, 111 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.

Flat in Kissimmee

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

Waterfront house rentals

A tranquil outdoor space features a private pool under a protective screen enclosure, framed by reclining lounge chairs. The setting offers a view of the lake, contrasting with the colorful sunset sky, creating a serene atmosphere for relaxation.

4.98 out of 5 average rating, 106 reviews

Mickey's Lakefront Villa at Sunset Lakes

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.

4.87 out of 5 average rating, 256 reviews

3 bedroom Villa in Kissimmee

4.98 out of 5 average rating, 145 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.

4.97 out of 5 average rating, 175 reviews

Waterfront Wizarding Near Universal's Harry Potter

4.8 out of 5 average rating, 176 reviews

#2718 Stunning LakeFront Priv Spa Pool Disney Epic

The exterior of the home showcases a single-story structure with a combination of pastel hues and stone accents. Lush green grass surrounds the building, accompanied by a variety of tropical plants and a palm tree. A well-maintained driveway leads to a two-car garage.

4.87 out of 5 average rating, 126 reviews

Relaxing Orlando 4 BR home, pool & water view

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

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.

4.81 out of 5 average rating, 146 reviews

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

Waterfront apartment rentals

An open-concept living area features a light-colored sectional sofa and a glass-top coffee table on a soft area rug. In the background, a modern kitchen with white cabinetry and stainless-steel appliances is visible, accompanied by three bar stools at the counter.

4.9 out of 5 average rating, 102 reviews

Luxury Lake View Near Convention Center, Universal

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, 106 reviews

IS3-205 Lakefront Condo - Close to All Attractions

4.94 out of 5 average rating, 131 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

4.93 out of 5 average rating, 164 reviews

The image features a collage showcasing Bahama Bay Resort. A tropical exterior with vibrant orange and white colors is presented alongside an elegantly styled bedroom. An inviting dining setup with wine bottles is highlighted next to a serene beach scene, complete with palm trees and lounge chairs.

Apartment in Davenport

Island Style at Bahama Bay - Minutes to Disney!

4.92 out of 5 average rating, 194 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.

Apartment in Kissimmee

3171-206 Resort Lake View Disney Universal Orlando

4.85 out of 5 average rating, 184 reviews

An aerial view captures the sandy beach area lined with palm trees and shaded cabanas. Lounge chairs are arranged neatly in front of the beach, while a pool area with vibrant blue water is visible in the background surrounded by lush landscaping.

Apartment in Davenport

Full-Service Gated Resort, Disney, Universal, MCO!

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, 119 reviews

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

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.