Holiday rentals with lake access in Winter Park

Find and book unique lake access rentals on Airbnb

Top-Rated Accommodation with Lake Access in Winter Park

Guests agree: These options for accommodation with lake access are highly rated for location, cleanliness and more.

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Top Guest favourite
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
4.97 out of 5 average rating, 224 reviews

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.

Top Guest favourite
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
4.94 out of 5 average rating, 153 reviews

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.

Guest favourite
A spacious pool house is visible behind a lush, green lawn, surrounded by trees. A paved path leads to the inviting pool area, while a gated fence provides added privacy. Sunlight filters through the leaves, creating dappled patterns on the grass.
Bungalow in Maitland
4.87 out of 5 average rating, 592 reviews

Maitland-Orlando Area, FL. Pool House Bungalow

Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

Top Guest favourite
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.
Guest suite in Altamonte Springs
4.96 out of 5 average rating, 368 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

Guest favourite
A private pool area is showcased with comfortable seating arranged around the water. Potted plants add greenery, while umbrellas provide shade. The tranquil view of Lake Concord is visible in the background, framed by lush trees and foliage.
Cottage in College Park
4.92 out of 5 average rating, 144 reviews

EdgeWater HideAway Overlooking Lake Concord

The EdgeWater HideAway is a private guesthouse, just minutes from Downtown Orlando, nestled within a suburban-like environment. The host greets/escorts you down a garden pathway where the ambient tranquility generates a sense of arrival at a place for rest and relaxation: Garden patio, private pool/sundeck and porch; all overlooking beautiful Lake Concord and the picturesque skyline of downtown Orlando. Minutes away there's great shopping, dining/entertainment, and all the sports arenas.

Top Guest favourite
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.
Place to stay in Audubon Park
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

Guest favourite
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
4.94 out of 5 average rating, 109 reviews

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 favourite
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 Wadeview Park
4.86 out of 5 average rating, 322 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.

Top Guest favourite
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.

Top Guest favourite
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 Lake Underhill
4.93 out of 5 average rating, 388 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

Top Guest favourite
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
5 out of 5 average rating, 467 reviews

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”.

Top Guest favourite
The tranquil scene captures a lakeside view framed by trees at dusk. The horizon glows with soft orange and yellow hues, reflecting on the water. A hammock is visible, adding to the serene atmosphere of the wetlands beyond.
Guest suite in St. Cloud
4.94 out of 5 average rating, 399 reviews

LAKE FRONT Suite w FREE Kayaking/Canoe

Private Master Suite with it's own exclusive entry. It has a convenient kitchenette complete with mini refrigerator, microwave, toaster, toaster oven and an outside grill. Comfy Queen size bed with overhead ceiling fan. Private Bathroom and shower. Lake view from the front of property, unit is in the back overlooking wetlands. Plenty of parking, with enough room to bring a boat.

Popular amenities for Winter Park lake access rentals

When is the best time to visit Winter Park?

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Avg. price$291 NZD$323 NZD$274 NZD$255 NZD$245 NZD$222 NZD$240 NZD$236 NZD$241 NZD$212 NZD$282 NZD$243 NZD
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Quick stats about holiday rentals with lake access in Winter Park

  • Total holiday rentals

    Explore 50 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at $34 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,160 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Winter Park holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Winter Park rentals

  • 4.8 Average rating

    Winter Park stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Winter Park's top spots, include Orlando Science Center, Harry P. Leu Gardens, and Orlando Museum of Art

Destinations to explore