Vacation rentals in Lake Osceola

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Top-rated vacation rentals in Lake Osceola

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

Guest favorite

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.

Nov 1 – 8

$99 per night
Guest favorite

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.

Jun 15 – 22

$109 per night
Guest favorite

Guest suite in Orlando

4.98 out of 5 average rating, 296 reviews

A SUITE RETREAT with a Garden View in the City

A lovely remodeled in-law suite in a 1920s Mission Styled home in College Park suited for 2 people with a separate entrance, private bath & a little kitchenette.The Suite looks out into a garden to offer a relaxing view. Even though you are in the Downtown area, the suite was designed to offer solitude. We are walking distance to many restaurants & only an easy 5 minute drive to downtown Orlando. I am looking forward to hosting any and all who would like to visit. All are welcome. #STR-1009437

Mar 13 – 20

$69 per night

Popular amenities for Lake Osceola vacation rentals

Other great vacation rentals in Lake Osceola

Guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 381 reviews

Guest Suite! Key West in Altamonte Springs!

Nov 14 – 21

$82 per night
Superhost

Guest suite in Orlando

4.85 out of 5 average rating, 190 reviews

Backyard Paradise! Studio Guesthouse with Patio

May 13 – 20

$62 per night
Guest favorite

Guest suite in Orlando

4.94 out of 5 average rating, 188 reviews

Luxury Suite Near Disney & Downtown Orlando

Apr 6 – 13

$89 per night
Guest favorite

Guesthouse in Orlando

4.89 out of 5 average rating, 600 reviews

Thornton Park's Historic Guest House - private

Sep 29 – Oct 6

$71 per night
Guest favorite

Guest suite in Casselberry

4.8 out of 5 average rating, 250 reviews

“Jungle Hideout” w/ Pool near (Orlando) WinterPark

Apr 20 – 27

$78 per night
Guest favorite

Loft in Orlando

4.87 out of 5 average rating, 1090 reviews

Downtown (Ivanhoe Village) Loft Apartment

Jan 8 – 15

$85 per night
Guest favorite

Guesthouse in Orlando

4.97 out of 5 average rating, 284 reviews

Oasis Garden Cottage -cozy, chic, near everything!

Sep 2 – 9

$96 per night
Guest favorite

Camper/RV in Winter Park

4.96 out of 5 average rating, 158 reviews

Babs & Dan's Place - Home away from Home

Apr 7 – 14

$47 per night
Superhost

Guest suite in Winter Park

4.94 out of 5 average rating, 81 reviews

Romantic Villa at Winter Park 1Bed 1Bath

Nov 23 – 30

$88 per night
Guest favorite

Home in Maitland

5.0 out of 5 average rating, 20 reviews

Fern Park Retreat

Oct 22 – 29

$103 per night
Superhost

Condo in Winter Park

4.8 out of 5 average rating, 55 reviews

Lovely Winter Park Home close to Hospitals !

Jul 5 – 12

$90 per night
Guest favorite

Home in Winter Park

5.0 out of 5 average rating, 28 reviews

Stunning Luxury Oasis + Nintendo-themed Game Room

Apr 24 – May 1

$677 per night

Destinations to explore

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