Vacation rentals with lake access in Winter Park

Find and book unique lake-access rentals on Airbnb

Top-rated lake-access accommodations in Winter Park

Guests agree: these lake-access accommodations are highly rated for location, cleanliness, and more.

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Guest favourite

Yurt in Orlando

4.96 out of 5 average rating, 221 reviews

Lakefront Sunset Yurt King Bed *A/C* Kayaks, Bikes

The Orlando Yurt Experience for Adults Only brought to you by CasaMarchanOrlando. Imagine Laying in Bed, Just Feet From the Water, Watching the Sunset from Yurt Deck. ★★★★★ "This yurt was the best experience l've ever had! I literally did not want to leave and I'm definitely coming back!” Xavier - April 2024 400sf Yurt King Bed Private Lakeside Deck & Outdoor Bathroom & Shower for 2. Indoor & Outdoor Dining Areas. BBQ, Alexa Controlled A/C. Free Unlimited Use of Kayaks & Bikes.

May 27 – Jun. 1

$187 CAD per night

Guest favourite

Bungalow in Maitland

4.86 out of 5 average rating, 490 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.

Jul. 14 – 21

$162 CAD per night

Guest favourite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 315 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

Jan. 4 – 11

$149 CAD per night

Superhost

Guesthouse in Orlando

4.85 out of 5 average rating, 265 reviews

★ Lakefront Bungalow-5min Downtown ★Casa Pura Vida

Our little piece of paradise is located within 5-10 minutes of Downtown Orlando where some of the best restaurants, bars, and attractions Orlando has to offer. Winter Park & College Park are 10-15 minute drives, Disney/Universal only 20- 30 minutes. The interior is zen and inviting, with a homey feel. Enjoy the Lakefront view, play on the Lake with water toys , soak in the sun on the beach, curl up on the porch with a coffee and enjoy the view. So peaceful, you’ll have a hard time leaving.

Sep. 25 – Oct. 2

$217 CAD per night

Guest favourite

Guesthouse in Orlando

4.96 out of 5 average rating, 366 reviews

The Coach House- 2 bedroom/3 bath Orlando Getaway!

Pet-friendly 2 Bedroom/3 Bath House. Designed by renowned architect James Gamble Rogers II, the house is a 25-minute drive ($23 Uber) from the MCO Airport. Nestled in the heart of Orlando's College Park district, it is an oasis just moments away from Downtown Orlando: nightlife, museums, and funky art and music scene. Take a 25-minute drive into Disney, Universal, or The Outlets. Uber/Lyft/Walk to nearby trendy restaurants, museums, theaters, boutique shopping, and our craft beer scene.

Jul. 26 – Aug. 2

$245 CAD per night

Guest favourite

Guesthouse in Orlando

4.88 out of 5 average rating, 218 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.

Sep. 13 – 20

$200 CAD per night

Guest favourite

Tiny homes in Orlando

4.88 out of 5 average rating, 369 reviews

The View - Waterfront Tiny Home

The View is a one of a kind tiny home- modern style mixed with comfortable textures and an unforgettable view of the lake. You won’t want to get out of bed with a view like this! This house features large picture windows, a comfortable living room, and a large private deck to make your stay a memorable one. Your tiny house stay won’t be a tiny experience...relax and unwind, enjoy sunrise yoga by the lake, and use our amenities to fish, kayak, and explore the natural beauty of Orlando!

Feb. 1 – 8

$255 CAD per night

Guest favourite

Guest suite in Orlando

4.97 out of 5 average rating, 243 reviews

Unique Place! East End Market! Baldwin/Winter Park

Welcome to Orlando. This unique place has private entrance, living room with microwave/refrigerator/freezer/Keurig coffee maker/55” TV and bathroom with a private overlooking little hidden garden/patio. There is a queen sized pull out couch in living room with a one time fee $15. I live in the actual back of the house and I am happy to assist you with anything you need. You can search in YouTube for “Faranak Guest House - winter/Baldwin-Park” to watch the short video about the unit.

Jun. 29 – Jul. 6

$246 CAD per night

Guest favourite

Guest suite in Orlando

4.92 out of 5 average rating, 316 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

May 7 – 14

$260 CAD per night

Guest favourite

Cottage in Orlando

4.96 out of 5 average rating, 141 reviews

Mills Cottage

Beautiful private upstairs cottage with deck overlooking the lake. Several other lakes and dog friendly parks are close. Comfort was the number one reason when choosing furniture and mattresses. Kitchen is fully equipped: coffee maker, toaster, microwave, cook top oven, refrigerator, washer/dryer, iron & flat screen TV. Free wifi, cable, Amazon Prime & Netflix. Also has a dedicated professional work space and desk. Includes light breakfast and snacks.

Aug. 17 – 24

$346 CAD per night

Guest favourite

Guest suite in Orlando

5.0 out of 5 average rating, 430 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”.

Jan. 6 – 13

$336 CAD per night

Guest favourite

Guesthouse in Orlando

4.98 out of 5 average rating, 350 reviews

Lakefront Seclusion modern guesthouse+Pool+Hot tub

An oasis in the city is what you will be surprised to find here at your guest house, located on a peaceful estate on the shore of Lake Hourglass. Secluded from the noises of the city, but still just minutes from everything, it's the perfect base to explore Orlando from, or perhaps to enjoy a staycation at if you're a local! For check out, please just enjoy your stay with us, you don’t need do any tidy or clean steps for us.

Sep. 17 – 24

$335 CAD per night