Vacation rentals in Winter Park

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Top-rated holiday rentals in Winter Park

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

Guest favourite
Apartment in Winter Park
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.
22 – 29 Dec
4.95 out of 5 average rating, 280 reviews
Guest favourite
Townhouse in Winter Park
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 June
4.98 out of 5 average rating, 193 reviews
Guest favourite
Bungalow in Winter Park
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
16 – 23 Aug
4.98 out of 5 average rating, 222 reviews

Popular amenities for Winter Park holiday rentals

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 holiday rentals in Winter Park

Guest favourite
Guesthouse in Orlando
Lovely Spacious Guesthouse in Mills 50 District
21 – 28 Feb
4.84 out of 5 average rating, 191 reviews
Guest favourite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
25 Nov – 2 Dec
4.98 out of 5 average rating, 295 reviews
Guest favourite
Guest suite in Orlando
Backyard Paradise! Studio Guesthouse with Patio
16 – 23 May
4.85 out of 5 average rating, 189 reviews
Guest favourite
Guesthouse in Winter Park
Tiny Cottage - 3 MI to Downtwn w/ Grill & Hammocks
5 – 12 June
4.92 out of 5 average rating, 263 reviews
Superhost
Guesthouse in Orlando
8th Green Cottage - A relaxing oasis in the city
2 – 9 May
4.91 out of 5 average rating, 137 reviews
Superhost
Home in Winter Park
ꜱʟᴇᴇᴘꜱ 4, ᴡɪɴᴛᴇʀ ᴘᴀʀᴋ & ᴅᴏᴡɴᴛᴏᴡɴ
10 – 17 May
4.9 out of 5 average rating, 39 reviews
Guest favourite
Apartment in Winter Park
The Lake House
21 – 28 Aug
4.88 out of 5 average rating, 25 reviews
Superhost
Condo in Winter Park
Lovely Winter Park Home close to Hospitals !
18 – 25 Aug
4.81 out of 5 average rating, 54 reviews
Guest favourite
Tiny home in Winter Park
Comfy Tiny Home @WP. Large Private Deck+Queen bed
21 – 28 May
4.88 out of 5 average rating, 17 reviews
Guest favourite
Condo in Winter Park
Walk to Park Ave & The WP Village!
4.94 out of 5 average rating, 35 reviews
Guest favourite
Home in Winter Park
Modern, Quiet & Cozy - Entire house /Winter park
23 – 30 Apr
4.93 out of 5 average rating, 103 reviews
Guest favourite
Home in Winter Park
LUXURY 𝕄𝕚𝕕 ℂ𝕖𝕟𝕥𝕦𝕣𝕪 𝕄𝕠𝕕𝕖𝕣𝕟 ᴠᴀᴄᴀᴛɪᴏɴ in 𝒲𝒾𝓃𝓉𝑒𝓇 𝒫𝒶𝓇𝓀
12 – 19 Nov
4.89 out of 5 average rating, 92 reviews

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