Holiday rentals in Orlando

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Top-rated holiday rentals in Orlando

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

Guest favourite
Flat 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 DecIndividual Host,
€ 133 per night
4.95 out of 5 average rating, 280 reviews
Guest favourite
Loft in Orlando
Contemporary Loft Near Downtown
Conveniently located between the foodie-friendly Milk District and The City Beautiful’s Downtown, this impeccably thought-out space features a spacious loft style open floor plan perfect for a couple or small group. The floor to ceiling windows allow natural light to fill the space while providing complete privacy during your stay. Upscale Winter Park restaurants and the vibrant Thornton Park art scene are only a short drive away. Universal is a 20 minute drive, Disney is 35 min., MCO 20 minutes
12–19 AprIndividual Host,
€ 172 per night
4.94 out of 5 average rating, 449 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 JunIndividual Host,
€ 144 per night
4.98 out of 5 average rating, 193 reviews

Popular amenities for Orlando holiday rentals

Stay near Orlando's top sights

Universal CityWalk991 locals recommend
Orlando Vineland Premium Outlets1,502 locals recommend
The Florida Mall656 locals recommend
The Mall at Millenia1,167 locals recommend
Outlets Orlando116 locals recommend
Amway Center259 locals recommend

Other great holiday rentals in Orlando

Guest favourite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
25 Nov – 2 DecIndividual Host,
€ 90 per night
4.98 out of 5 average rating, 295 reviews
Guest favourite
Home in Winter Garden
Cozy Winter Garden Home 20 MINUTES FROM DISNEY
1–8 AugIndividual Host,
€ 127 per night
4.92 out of 5 average rating, 164 reviews
Guest favourite
Guest house in Orlando
Stylish Private Studio in Downtown Orlando
10–17 JunIndividual Host,
€ 135 per night
4.95 out of 5 average rating, 124 reviews
Guest favourite
Guest house in Orlando
Lakefront Seclusion modern guesthouse+Pool+Hot tub
9–16 AugIndividual Host,
€ 229 per night
4.98 out of 5 average rating, 342 reviews
Guest favourite
Guest suite in Orlando
Be Our Guest! 1 BR/1 Bath Guest Room
26 Jun – 3 JulIndividual Host,
€ 87 per night
4.98 out of 5 average rating, 125 reviews
Guest favourite
Cottage in Davenport
$79! Cozy Cottage + Outdoor Fun -Close to Disney!
10–17 MayIndividual Host,
€ 105 per night
4.92 out of 5 average rating, 122 reviews
Guest favourite
Guest house in Winter Park
Private and Peaceful with Full Kitchen
7–14 JunIndividual Host,
€ 112 per night
4.98 out of 5 average rating, 243 reviews
Guest favourite
Guest suite in Orlando
The Groves (2)
4–11 SepIndividual Host,
€ 56 per night
4.88 out of 5 average rating, 523 reviews
Guest favourite
Guest house in Orlando
Couples Oasis Heated Pool and Lake View
17–24 MayProfessional Host,
€ 135 per night
4.87 out of 5 average rating, 206 reviews
Guest favourite
Guest house in Orlando
The Loft in College Park
21–28 AprIndividual Host,
€ 89 per night
4.98 out of 5 average rating, 139 reviews
Guest favourite
Yurt in Orlando
Nature's Yurt: Lakefront Haven at Belle Lac
12–17 MayIndividual Host,
€ 173 per night
4.97 out of 5 average rating, 64 reviews
Guest favourite
Guest house in Orlando
Guesthouse hosted by Yadier
23–30 MayIndividual Host,
€ 127 per night
5.0 out of 5 average rating, 44 reviews

Quick stats about holiday rentals in Orlando

Total rentals

10K properties

Rentals with dedicated workspaces

5.8K properties have a dedicated workspace

Rentals with a pool

7.3K properties have a pool

Pet-friendly rentals

2.1K properties allow pets

Family-friendly rentals

5.5K properties are a good fit for families

Total number of reviews

286K reviews

Destinations to explore

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