Winter Springs vacation rentals

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Top-rated vacation rentals in Winter Springs

Guests agree: these vacation rentals 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

€ 133 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

€ 145 per night
Guest favorite

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

May 21 – 28

€ 98 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 favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 137 reviews

Comfortable Guest Suite-Stylish Altamonte Springs!

Aug 8 – 15

€ 133 per night
Guest favorite

Home in Winter Park

4.9 out of 5 average rating, 122 reviews

Guest Suite in Winter Park/Orlando

Aug 5 – 12

€ 83 per night
Superhost

Farm stay in Orlando

4.9 out of 5 average rating, 156 reviews

Charming Guesthouse at Pine & Oak Place

Sep 12 – 19

€ 135 per night
Guest favorite

Guesthouse in Winter Park

4.81 out of 5 average rating, 231 reviews

WELCOME HOME IN WINTER PARK

Dec 13 – 20

€ 114 per night
Superhost

Apartment in Maitland

4.82 out of 5 average rating, 169 reviews

At Mine | Double Suite in Orlando

Oct 10 – 17

€ 77 per night
Guest favorite

Guesthouse in Maitland

4.98 out of 5 average rating, 114 reviews

Private 1-bd Mid-Century Guesthouse

Jul 28 – Aug 4

€ 113 per night
Guest favorite

Home in Apopka

4.96 out of 5 average rating, 184 reviews

Farm feel in the city

Aug 20 – 27

€ 142 per night
Guest favorite

Home in Lake Mary

4.82 out of 5 average rating, 249 reviews

Independent Unique Guest house lake/kayaks/jacuzzy

Jun 14 – 21

€ 163 per night
Guest favorite

Home in Sanford

4.95 out of 5 average rating, 130 reviews

The Sanford Bokey Pokey

Dec 3 – 10

€ 126 per night
Superhost

Home in Altamonte Springs

4.83 out of 5 average rating, 158 reviews

Guest House near attractions

Aug 9 – 16

€ 123 per night
Guest favorite

Guest suite in Geneva

4.95 out of 5 average rating, 218 reviews

The Weathered Inn at Cedar Knoll Flying Ranch

May 8 – 15

€ 150 per night
Guest favorite

Guest suite in Lake Mary

4.95 out of 5 average rating, 103 reviews

Quiet, Upscale Studio

Oct 10 – 17

€ 104 per night

Other great vacation rentals in Winter Springs

Guest favorite

Home in Winter Springs

4.96 out of 5 average rating, 24 reviews

Just like home-specious 4 bedroom

Aug 31 – Sep 7

€ 246 per night
Guest favorite

Guesthouse in Sanford

4.91 out of 5 average rating, 68 reviews

Suite Retreat

Oct 31 – Nov 7

€ 83 per night
Guest favorite

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

€ 96 per night
Superhost

Guest suite in Winter Park

4.94 out of 5 average rating, 81 reviews

Romantic Villa at Winter Park 1Bed 1Bath

May 26 – Jun 2

€ 105 per night
Guest favorite

Apartment in Orlando

5.0 out of 5 average rating, 63 reviews

Parent's Retreat!

Jul 7 – 14

€ 120 per night
Guest favorite

Guesthouse in Longwood

5.0 out of 5 average rating, 63 reviews

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

Jul 6 – 13

€ 143 per night
Guest favorite

Home in Maitland

5.0 out of 5 average rating, 20 reviews

Fern Park Retreat

Oct 22 – 29

€ 127 per night
Guest favorite

Guesthouse in Lake Mary

4.99 out of 5 average rating, 77 reviews

Sunset Cottage in Lake Mary, Florida

Sep 8 – 15

€ 137 per night
Guest favorite

Home in Altamonte Springs

4.93 out of 5 average rating, 15 reviews

Modern, Luxurious & Spacious 1/1

Aug 17 – 24

€ 134 per night
Superhost

Home in Winter Springs

4.88 out of 5 average rating, 8 reviews

Pure Vida - Your home away from home!

Dec 10 – 17

€ 209 per night
Guest favorite

Home in Longwood

5.0 out of 5 average rating, 29 reviews

One Love Retreat and Guest House

May 28 – Jun 4

€ 172 per night
Guest favorite

Bungalow in Winter Park

4.87 out of 5 average rating, 63 reviews

Charming Farmhouse Bungalow

Sep 8 – 15

€ 132 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

€ 9 before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Winter Springs?

    Yes! Work meets play with ease at over 30 vacation rentals in Winter Springs featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winter Springs?

    Four-legged friends are welcome in Winter Springs. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there Winter Springs vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Winter Springs, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in house rentals in Winter Springs?

    Experience the best of Winter Springs with our house rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Winter Springs have wireless internet?

    Absolutely! We offer over 50 house rentals with wireless internet in Winter Springs. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Winter Springs?

    Winter Springs has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Winter Springs have air conditioning?

    Absolutely! We offer over 50 house rentals with air conditioning in Winter Springs. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Winter Springs?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with air conditioning, over 50 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore