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Winter Springs Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Winter Springs holiday rentals

A swimming pool with a unique light display creating patterns on the water's surface.

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
The price is AU$374
includes taxes & fees
9 Nov - 10 Nov
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A modern kitchen with white cabinets, a wooden countertop, and a built-in oven.

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

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (23 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.
The price is AU$366
includes taxes & fees
1 Nov - 2 Nov
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

3. 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)
"Everything about the house was great. Great house for the price!"
United States
Charles T.
The price is AU$357
includes taxes & fees
2 Nov - 3 Nov
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
A swimming pool with lounge chairs and palm trees.

4. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,463 reviews)
"This is a great place to stay"
United States
Susan
The price is AU$120
includes taxes & fees
2 Nov - 3 Nov
The Point Hotel & Suites Orlando
A sign with 'The Wellborn' written on it, surrounded by lush greenery and a building in the background.

5. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (343 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
The price is AU$149
includes taxes & fees
23 Nov - 24 Nov
Suites by The Wellborn
A compact workspace with a laptop, a desk lamp, a notebook, and a cup.

6. 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.
The price is AU$202
includes taxes & fees
11 Nov - 12 Nov
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
A modern kitchen with a marble countertop, gold faucets, and a large window.

7. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (23 reviews)
"The location was perfect, can walk to restaurants easily. Unit was very clean and nicely designed, would stay again"
United States
Sara
The price is AU$232
includes taxes & fees
9 Nov - 10 Nov
Bella Breeze
A backyard with a hammock, outdoor seating, and string lights.

8. 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
The price is AU$207
includes taxes & fees
8 Nov - 9 Nov
The Jazz Loft
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, a door, and a painting on the wall.

9. 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.
The price is AU$366
includes taxes & fees
2 Nov - 3 Nov
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
IMG 8991

10. 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
The price is AU$257
includes taxes & fees
1 Nov - 2 Nov
The Blue Aztec
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.

11. 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
The price is AU$334
includes taxes & fees
15 Nov - 16 Nov
The Front Porch
A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

12. 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
The price is AU$510
includes taxes & fees
1 Nov - 2 Nov
Tranquil 3-bedroom house in Sanford with AC, WiFi
A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

13. 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, (2,210 reviews)
"Great stay Large comfortable.room Reasonable price"
United States
Martyn
The price is AU$134
includes taxes & fees
30 Nov - 1 Dec
The View Hotel, Trademark Collection by Wyndham
Private kitchen

14. Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Apopka
9.8 out of 10, Exceptional, (8 reviews)
"Great place to stay. We plan on staying again."
United States
Nancee H.
The price is AU$200
includes taxes & fees
2 Nov - 3 Nov
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
A front door with a glass panel, a wreath, and a doormat with a welcoming message.

15. Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!

Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
College Park
10.0 out of 10, Exceptional, (3 reviews)
"Quiet location, easy access to many amenities.Host genuinely cares about the clienteles well being and that needs are accommodated for if required."
Canada
Kevin G.
The price is AU$269
includes taxes & fees
3 Nov - 4 Nov
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
A modern kitchen with red walls, a dining area with a brown leather couch, and a bar stool.

16. 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.
The price is AU$267
includes taxes & fees
1 Nov - 2 Nov
Downtown Cottage
A bedroom with a bed, a ceiling fan, and artwork on the walls.

17. Downtown Private Efficiency Lake Eola Central Business District

Downtown Private Efficiency Lake Eola Central Business District
Downtown Orlando
9.6 out of 10, Exceptional, (68 reviews)
"It's a nice spot tucked right in the heart of Orlando! Perfect for solo travelers or couples. It's bigger and better than the hotels nearby. Plus it includes free parking and is cheaper than a hotel!"
United States
Noah
The price is AU$214
includes taxes & fees
1 Dec - 2 Dec
Downtown Private Efficiency Lake Eola Central Business District
A modern kitchen with wooden cabinets, a black countertop, a stainless steel refrigerator, a microwave, and a coffee maker.

18. Stylish & Cozy King Bed Retreat @ Baldwin Park

Stylish & Cozy King Bed Retreat @ Baldwin Park
Orlando
10.0 out of 10, Exceptional, (21 reviews)
"It was a cute property and in a great location to get anywhere in the area"
United States
Devan S.
The price is AU$491
includes taxes & fees
1 Nov - 2 Nov
Stylish & Cozy King Bed Retreat @ Baldwin Park
A modern kitchen with grey cabinets, a wooden countertop, and a built-in stove.

19. 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.
The price is AU$238
includes taxes & fees
2 Nov - 3 Nov
Lake Eola view 1 bedroom Thornton Park
A modern kitchen with a dining area, a black sofa, and a painting of a sunset.

20. Cozy studio in fabulous Orlando close to everything

Cozy studio in fabulous Orlando close to everything
Orlando
10.0 out of 10, Exceptional, (22 reviews)
"Super cute would stay here again"
United States
Kristen a.
The price is AU$227
includes taxes & fees
11 Nov - 12 Nov
Cozy studio in fabulous Orlando close to everything
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

Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport

8/10 Good
"It was a In-N-Out situation when I got there. 10 minutes later I was already on my way with my Venom."
Edwin J 1-night trip
Posted less than an hour ago
Wingate by Wyndham - Orlando International Airport

Find out more about Winter Springs

Everything you need to know about Winter Springs holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Springs holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winter Springs holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter Springs holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter Springs holiday rentals we have selected for you start as low as AU$85 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winter Springs rentals

At Expedia, we put the best Winter Springs holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Winter Springs?

Yes, there are holiday rentals close to the most popular sights 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 holiday rentals that Winter Springs has to offer?

Salt Pool, cozy House near Downtown and International Airport: This holiday home rental outside of Winter Springs is located in the city centre, and has a garden, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Winter Springs?

Expedia has 9 holiday 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 such as Universal Orlando Resort and Kia Center.

What’s a holiday rental in Winter Springs like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winter Springs. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips.