Vacation rentals in Winter Park

Find and book unique accommodation on Airbnb

Top-rated accommodation in Winter Park

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Apartment in Winter Park

4.95 out of 5 average rating, 280 reviews

Get a Little Glam in a Retro Palm Beach-Style Boudoir

The whole upstairs portion of the building is all yours. Location is prime as it is close to all things wonderful in Winter Park FL. Two streets behind is Lake Killarney. The space is beautifully decorated and offers guests a charming get away. Please note: It is a 13.6 mile drive (21 - 40 minutes depending on traffic) from Universal Studio's and a 21.7mile drive (24 - 45 minutes depending on traffic) to Disney World. There is a lock box located under the stairwell on the left side of the building. I will message you with your code for access. Once you get your key, head on up the stairs and enjoy your home away from home. Welcome! I live 3 minutes away from the Air BnB property and I work in the downstairs portion of the building, so I am local and available to assist with any additional requests. Message me anytime! Or text 407 575 3502 The Fairbanks corridor of Winter Park is the main artery to affluent areas, offering great shopping and dining close by. This hidden gem is a short walk to grocery stores, restaurants, and Winter Park Village shopping district with its movie theater. Light sleepers, please be aware that there is the potential for traffic noise. The BnB offers a large parking lot. You should have no problem at all if you desire to arrive by car. The area is also safe to bike around and Uber or Lyft operates in the area. No smoking please.

1–8 Nov

$240 NZD per night
Guest favourite

Townhouse in Winter Park

4.98 out of 5 average rating, 195 reviews

Beautiful Downtown Winter Park

WP requires rentals to be listed as 28 days. For alternate rentals please contact me with dates requested. A 1 bedroom New England style townhouse. Enjoy brick streets, old oaks and lake access all within a 5 minute walk to downtown Winter Park, home of nationally known art festivals and museums, Saturday farmers market, Rollins College and many fine dining establishments. Pick herbs from our garden to use in cooking. Lounge on your private deck to the relaxing waterfall sounds of our koi pond.

15–22 Jun

$261 NZD per night
Guest favourite

Bungalow in Winter Park

4.98 out of 5 average rating, 224 reviews

Cozy 2/2 Bungalow - Downtown Winterpark/Orlando

Your family will be close to everything when you stay at this centrally-located bungalow. Located right off I-4, you will be 5 minutes from Downtown Orlando and Downtown Edgewater, 10 min from Downtown Winter Park, 15 min from Universal Studios, and 25 min from Disney! College Park local parks and golf course within walking distance! Large 70 inch 4K tv with surround sound, large sofa to enjoy watching your favorite movies, 2 rooms with queen beds, and 2 bathrooms equipped with bluetooth music

11–18 Sep

$305 NZD per night

Popular amenities for Winter Park accommodation

Stay near Winter Park's top sights

Orlando Science Center289 locals recommend
Winter Park Village68 locals recommend
Harry P. Leu Gardens197 locals recommend
AdventHealth Orlando25 locals recommend
Trader Joe's74 locals recommend
Mead Botanical Garden52 locals recommend

Other great accommodation in Winter Park

Guest favourite

Guesthouse in Orlando

4.94 out of 5 average rating, 127 reviews

Jefferson St. Cottage

8–15 Jul

$205 NZD per night
Guest favourite

Home in Winter Park

4.93 out of 5 average rating, 102 reviews

Modern, Quiet & Cozy - Entire house /Winter park

23–30 Aug

$330 NZD per night
Guest favourite

Guest suite in Orlando

4.97 out of 5 average rating, 238 reviews

Unique Place! East End Market! Baldwin/Winter Park

31 May – 7 Jun

$264 NZD per night
Guest favourite

Campervan/RV in Winter Park

4.96 out of 5 average rating, 158 reviews

Babs & Dan's Place - Home away from Home

7–14 Apr

$110 NZD per night
Guest favourite

Apartment in College Park

4.95 out of 5 average rating, 613 reviews

Quiet Shed in Downtown

14–21 Dec

$233 NZD per night
Guest favourite

Guesthouse in Orlando

4.83 out of 5 average rating, 193 reviews

Lovely Spacious Guesthouse in Mills 50 District

8–15 Mar

$140 NZD per night
Guest favourite

Guesthouse in Orlando

4.97 out of 5 average rating, 284 reviews

Oasis Garden Cottage -cozy, chic, near everything!

2–9 Sep

$233 NZD per night
Superhost

Guest suite in Winter Park

4.94 out of 5 average rating, 81 reviews

Romantic Villa at Winter Park 1Bed 1Bath

23–30 Nov

$203 NZD per night
Superhost

Condo in Winter Park

4.8 out of 5 average rating, 55 reviews

Lovely Winter Park Home close to Hospitals !

5–12 Jul

$241 NZD per night
Guest favourite

Bungalow in Winter Park

4.87 out of 5 average rating, 63 reviews

Charming Farmhouse Bungalow

8–15 Sep

$238 NZD per night
Guest favourite

Home in Winter Park

5.0 out of 5 average rating, 28 reviews

Stunning Luxury Oasis + Nintendo-themed Game Room

24 Apr – 1 May

$1,511 NZD per night
Guest favourite

Apartment in Winter Park

4.89 out of 5 average rating, 28 reviews

The Lake House

20–27 Aug

$174 NZD per night

Quick stats about holiday rentals in Winter Park

Total rentals

410 properties

Rentals with dedicated workspaces

240 properties have a dedicated workspace

Rentals with a pool

100 properties have a pool

Pet-friendly rentals

140 properties allow pets

Family-friendly rentals

200 properties are a good fit for families

Total number of reviews

17K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Orange County
  5. Winter Park