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Winter Springs Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winter Springs vacation rentals

Relax in a cozy, candle-lit living space with plush seating and warm a lighting.

1. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (68 reviews)
"The Property was very clean ! Super convenient location and the perfect size for a family with 2 younger children ! Suzy was super nice !"
United States
Gary
$244 nightly
The price is $269
Nov 3 - Nov 4
Total with taxes and fees
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

2. Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Casselberry
9.8 out of 10, Exceptional, (58 reviews)
"This home was just what we needed, it was clean and comfortable. Great communication with the owner. Nice, safe neighborhood."
United States
Angie P.
$217 nightly
The price is $239
Oct 22 - Oct 23
Total with taxes and fees
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
A modern kitchen with white cabinets, a microwave, and a green wall with a neon sign.

3. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (22 reviews)
"We had an amazing stay! The place was beautiful, cozy, and incredibly comfortable. Even though we had to leave earlier than planned, we truly enjoyed our time here. The host was kind, responsive, and made everything easy from start to finish. We would definitely stay here again and look forward to returning in the future. Highly recommend!"
United States
Chiann M.
$223 nightly
The price is $246
Nov 2 - Nov 3
Total with taxes and fees
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Two hands holding cocktail glasses with garnishes, a balcony railing, and greenery in the background.

4. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (339 reviews)
"The check in process was smooth and did not require any front desk it was perfect for a quick stay! The room was pretty big for the price! and very clean. The property itself was cute and cozy they had a very cool common area! Love this stay"
United States
Dustin
$77 nightly
The price is $86
Oct 26 - Oct 27
Total with taxes and fees
Suites by The Wellborn
A compact workspace with a laptop, a desk lamp, a notebook, and a cup.

5. Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO

Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
Sanford
9.8 out of 10, Exceptional, (9 reviews)
"Perfect spot for a quick night after your flight into Sanford. Close to the airport, clean accommodations in a quiet neighborhood. Couldn’t ask for more!"
United States
Julia F.
$127 nightly
The price is $140
Oct 22 - Oct 23
Total with taxes and fees
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
A backyard with a hammock, outdoor seating, and string lights.

6. The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, Excellent, (9 reviews)
"Great overnight stay. Really cute loft. Would definitely stay again."
United States
Tiffany
$140 nightly
The price is $157
Oct 22 - Oct 23
Total with taxes and fees
The Jazz Loft
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, a door, and a painting on the wall.

7. Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
9.6 out of 10, Exceptional, (13 reviews)
"Very clean and hospitable. Recommend staying here for sure!"
United States
Kyle Y.
$232 nightly
The price is $258
Oct 22 - Oct 23
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
A modern kitchen with a marble countertop, gold faucets, and a large window.

8. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (22 reviews)
"The location was perfect, can walk to restaurants easily. Unit was very clean and nicely designed, would stay again"
United States
Sara
$155 nightly
The price is $174
Oct 24 - Oct 25
Total with taxes and fees
Bella Breeze
A swimming pool with lounge chairs and palm trees.

9. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,435 reviews)
"Enjoyed our stay and felt it was a great price for the location."
United States
Lisa
$83 nightly
The price is $93
Nov 4 - Nov 5
Total with taxes and fees
The Point Hotel & Suites Orlando
A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

10. Tranquil 3-bedroom house in Sanford with AC, WiFi

Tranquil 3-bedroom house in Sanford with AC, WiFi
Sanford
9.6 out of 10, Exceptional, (28 reviews)
"Beautiful place to stay near the airport "
United States
Rodney
$330 nightly
The price is $365
Oct 22 - Oct 23
Total with taxes and fees
Tranquil 3-bedroom house in Sanford with AC, WiFi
IMG 8991

11. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, Exceptional, (15 reviews)
"Everything was incredible and the owners were extremely helpful and accommodating! Would stay here again 100%!"
United States
Kael
$170 nightly
The price is $181
Oct 25 - Oct 26
Total with taxes and fees
The Blue Aztec
A house with a red door, a front porch, and a pathway leading to the entrance.

12. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (16 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
$167 nightly
The price is $186
Oct 25 - Oct 26
Total with taxes and fees
Downtown Cottage
A modern kitchen with a central island, built-in appliances, and a skylight.

13. Stylish Boutique Guest house in Winter Park

Stylish Boutique Guest house in Winter Park
Winter Park
10.0 out of 10, Exceptional, (110 reviews)
"We enjoyed a great stay! "
United States
Amanda B.
Stylish Boutique Guest house in Winter Park
A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

14. The View Hotel, Trademark Collection by Wyndham

The View Hotel, Trademark Collection by Wyndham
3.0 star property
Orlando
8.4 out of 10, Very good, (2,198 reviews)
"Excellent hotel and service in my first time in this hotel."
United States
Oscar
$82 nightly
The price is $92
Oct 25 - Oct 26
Total with taxes and fees
The View Hotel, Trademark Collection by Wyndham
A modern kitchen with grey cabinets, a wooden countertop, and a built-in stove.

15. Lake Eola view 1 bedroom Thornton Park

Lake Eola view 1 bedroom Thornton Park
South Eola
10.0 out of 10, Exceptional, (15 reviews)
"Clean and quiet spot with an easy check-in process. Super close to the lake with lots of restaurants within walking distance. Parking was easy to access and made getting in and out quite easy."
United States
Caroline V.
$152 nightly
The price is $168
Oct 22 - Oct 23
Total with taxes and fees
Lake Eola view 1 bedroom Thornton Park
A bedroom with a tufted headboard, striped pillows, a bed with a blue blanket, a gray rug, and a white closet with louvered doors.

16. Beautiful Studio near Int. Drive, Disney & Airport.

Beautiful Studio near Int. Drive, Disney & Airport.
Conway
9.4 out of 10, Exceptional, (25 reviews)
"Good place"
United States
Rodrigo
$134 nightly
The price is $148
Oct 26 - Oct 27
Total with taxes and fees
Beautiful Studio near Int. Drive, Disney & Airport.
A spacious lobby with a kitchen area, seating arrangements, and a view of the outdoors.

17. 2 Full Beds Non-Smoking

2 Full Beds Non-Smoking
Orlando FL
9.6 out of 10, Exceptional, (30 reviews)
"The staff were friendly and helpful during check in."
United States
Anonymous traveler
$60 nightly
The price is $67
Oct 22 - Oct 23
Total with taxes and fees
2 Full Beds Non-Smoking
A modern house with a garage, a well-maintained lawn, and decorative lighting along the pathway.

18. Cozy Private Apartment - Stylish & Spotless — No sharing areas

Cozy Private Apartment - Stylish & Spotless — No sharing areas
Orlando
10.0 out of 10, Exceptional, (39 reviews)
"Awesome place to stay! Clean as a whistle, and nice and private! "
United States
N T.
$172 nightly
The price is $191
Oct 22 - Oct 23
Total with taxes and fees
Cozy Private Apartment - Stylish & Spotless — No sharing areas
A bedroom with a bed, a ceiling fan, a stained glass window, and a door leading to another room.

19. TINY unit in cottage in the middle of Downtown

TINY unit in cottage in the middle of Downtown
Downtown Orlando
9.8 out of 10, Exceptional, (23 reviews)
"The unit was nice and clean. It was a close walk to the Kia Center. In a pretty quiet area."
United States
Paula
$133 nightly
The price is $148
Oct 26 - Oct 27
Total with taxes and fees
TINY unit in cottage in the middle of Downtown
A modern living room with a grey sofa, two armchairs, a coffee table, and a small side table with a lamp. There is a brick fireplace, a kitchen area with a countertop and cabinets, and a large window with blinds.

20. The Front Porch

The Front Porch
3.0 star property
Downtown Sanford
9.2 out of 10, Wonderful, (5 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
$295 nightly
The price is $330
Oct 26 - Oct 27
Total with taxes and fees
The Front Porch
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Springs Hotel Reviews

Grand Hotel Orlando at Universal Blvd - Shuttle to Theme Parks

Grand Hotel Orlando at Universal Blvd - Shuttle to Theme Parks

10/10 Excellent
"Una estadía excelente de principio a fin! Desde nuestra llegada, recibimos una atención amable y profesional por parte del personal. La habitación estaba limpia, cómoda y bien organizada, lo que nos permitió descansar y disfrutar de nuestra visita. Las instalaciones se encontraban en buenas condiciones y el ambiente fue agradable y tranquilo. Quiero destacar especialmente la hospitalidad del personal, siempre dispuesto a ayudar y hacer que los huéspedes se sientan bienvenidos. Sin duda, fue una experiencia muy positiva que superó nuestras expectativas. ¡Recomiendo este hotel y definitivamente volvería a hospedarme aquí en una próxima visita!"
WANDA 4-night trip
Posted less than an hour ago
Grand Hotel Orlando at Universal Blvd - Shuttle to Theme Parks

Find out more about Winter Springs

Everything you need to know about Winter Springs vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Springs vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Springs vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Springs vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Springs. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Springs in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $92 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Springs rentals

At Expedia, we put the best Winter Springs vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Springs rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Springs vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Springs. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winter Springs?

Yes, we give you a choice of vacation rentals near popular attractions in Winter Springs, or you can select a more secluded option if you're looking for a relaxing stay. Winter Springs is known for its temples and breweries. Make sure you have time to check out the baseball games and lake views during your trip.

What are some of the best vacation home rentals that Winter Springs has to offer?

Salt Pool, cozy House near Downtown and International Airport: Visitors like this Winter Springs vacation home rental. It is located in the city center and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchenette with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Winter Springs?

Expedia has 9 vacation rentals for your stay in Winter Springs.

What’s there to see and do in Winter Springs?

Boombah-Soldiers Creek Park and Central Winds Park are a couple of lovely local spots to get outside and enjoy nature. While in the area, you can also visit popular places like Universal Orlando Resort and Kia Center.

What’s a vacation rental in Winter Springs like?

A vacation rental is a private property where you can stay for a couple of days or more in Winter Springs. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.