Vacation rentals in Winter Springs

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winter Springs

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.

Nov. 1 – 8

$196 CAD 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.

Jun. 15 – 22

$213 CAD per night
Guest favourite

Guest suite in Altamonte Springs

4.97 out of 5 average rating, 295 reviews

St. Hemingway Suite

Very tranquil Romantic room with views and access to large lake. PRIVATE ENTRANCE and private bathroom. Amenities include, private dock, pool, large manicured lawns, private parking, breakfast kitchenette and much more. Close to theme parks and beaches. Ample shopping and award winning restaurants very nearby. Peaceful setting to read, do Yoga, enjoy quiet moments by the lake, watch the boats sail by or watch the sun rise. Peace and tranquility at its best. We welcome you to Spring Valley

Apr. 16 – 23

$143 CAD per night

Popular amenities for Winter Springs vacation rentals

Stay near Winter Springs's top sights

Oviedo Mall16 locals recommend
Townhouse Restaurant15 locals recommend
Regal Oviedo Mall10 locals recommend
Target6 locals recommend
Spring Hammock Preserve6 locals recommend
Publix Super Market at Winter Springs Town Center3 locals recommend

Other great vacation rentals in Winter Springs

Guest favourite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 137 reviews

Comfortable Guest Suite-Stylish Altamonte Springs!

Aug. 8 – 15

$195 CAD per night
Superhost

Farm stay in Orlando

4.9 out of 5 average rating, 156 reviews

Charming Guesthouse at Pine & Oak Place

Sep. 26 – Oct. 3

$198 CAD per night
Guest favourite

Home in Winter Park

4.9 out of 5 average rating, 123 reviews

Guest Suite in Winter Park/Orlando

Jun. 12 – 19

$129 CAD per night
Guest favourite

Guesthouse in Winter Park

4.81 out of 5 average rating, 231 reviews

WELCOME HOME IN WINTER PARK

Oct. 5 – 12

$167 CAD per night
Guest favourite

Guest suite in Winter Springs

4.97 out of 5 average rating, 64 reviews

Modern Guest Studio 15 mins from SFB Airport

Jun. 23 – 30

$135 CAD per night
Guest favourite

Home in Winter Springs

4.96 out of 5 average rating, 24 reviews

Just like home-specious 4 bedroom

Aug. 31 – Sep. 7

$361 CAD per night
Guest favourite

Guesthouse in Sanford

4.91 out of 5 average rating, 68 reviews

Suite Retreat

Oct. 31 – Nov. 7

$122 CAD per night
Guest favourite

Guesthouse in Lake Mary

4.98 out of 5 average rating, 59 reviews

Cozy Cottage in the heart of Lake Mary

Jul. 27 – Aug. 3

$140 CAD per night
Guest favourite

Apartment in Orlando

5.0 out of 5 average rating, 63 reviews

Parent's Retreat!

Jul. 7 – 14

$177 CAD per night
Guest favourite

Guesthouse in Longwood

5.0 out of 5 average rating, 63 reviews

"Winnie's Place" A Peaceful Guesthouse with Pool.

Jul. 6 – 13

$209 CAD 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

$165 CAD per night
Guest favourite

Home in Maitland

5.0 out of 5 average rating, 20 reviews

Fern Park Retreat

Oct. 22 – 29

$186 CAD per night

Quick stats about vacation rentals in Winter Springs

Total rentals

80 properties

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

2.8K reviews

Nightly prices starting at

$14 CAD before taxes and fees

Destinations to explore