Winter Springs Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winter Springs holiday rentals

An outdoor patio area with a covered seating area, lounge chairs, and a pool.

1. Traveler's Dream: Refresh & Recharge Poolside

Traveler's Dream: Refresh & Recharge Poolside
Casselberry
9.2 out of 10, Wonderful, (15 reviews)
"Easy check-in/out experience. Quaint and cozy. Just what we needed for our stay."
United States
Kaitlin G.
The price is NZ$239
includes taxes & fees
10 Nov - 11 Nov
Traveler's Dream: Refresh & Recharge Poolside
Relax in a cozy, candle-lit living space with plush seating and warm a lighting.

2. 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, (70 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 NZ$447
includes taxes & fees
10 Nov - 11 Nov
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A modern kitchen with white cabinets, a wooden countertop, and a built-in oven.

3. 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 NZ$438
includes taxes & fees
6 Dec - 7 Dec
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

4. 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 NZ$434
includes taxes & fees
10 Nov - 11 Nov
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
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, (344 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 NZ$137
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 NZ$238
includes taxes & fees
12 Nov - 13 Nov
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
A backyard with a hammock, outdoor seating, and string lights.

7. The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, Excellent, (10 reviews)
"Great overnight stay. Really cute loft. Would definitely stay again."
United States
Tiffany
The price is NZ$278
includes taxes & fees
4 Dec - 5 Dec
The Jazz Loft
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, (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 NZ$276
includes taxes & fees
10 Nov - 11 Nov
Bella Breeze
A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

9. Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
The price is NZ$285
includes taxes & fees
4 Dec - 5 Dec
Boho Nights
A swimming pool with lounge chairs and palm trees.

10. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,495 reviews)
"This is a great place to stay"
United States
Susan
The price is NZ$147
includes taxes & fees
22 Nov - 23 Nov
The Point Hotel & Suites Orlando
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, a door, and a painting on the wall.

11. 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 NZ$445
includes taxes & fees
10 Nov - 11 Nov
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
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.

12. 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 NZ$406
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.

13. 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
Tranquil 3-bedroom house in Sanford with AC, WiFi
IMG 8991

14. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, Exceptional, (17 reviews)
"Everything was incredible and the owners were extremely helpful and accommodating! Would stay here again 100%!"
United States
Kael
The price is NZ$312
includes taxes & fees
15 Nov - 16 Nov
The Blue Aztec
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, (4 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 NZ$310
includes taxes & fees
10 Nov - 11 Nov
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
Private kitchen

16. 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
9.4 out of 10, Exceptional, (9 reviews)
"It is very close to the restaurant, shops and parks"
United States
Naiviv
The price is NZ$225
includes taxes & fees
10 Nov - 11 Nov
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
A modern kitchen with wooden cabinets, a black countertop, a stainless steel refrigerator, a microwave, and a coffee maker.

17. Stylish & Cozy King Bed Retreat @ Baldwin Park

Stylish & Cozy King Bed Retreat @ Baldwin Park
Orlando
10.0 out of 10, Exceptional, (22 reviews)
"It was a cute property and in a great location to get anywhere in the area"
United States
Devan S.
The price is NZ$639
includes taxes & fees
10 Nov - 11 Nov
Stylish & Cozy King Bed Retreat @ Baldwin Park
A bedroom with a bed, a ceiling fan, a stained glass window, and a door leading to another room.

18. 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, (24 reviews)
"The unit was nice and clean. It was a close walk to the Kia Center. In a pretty quiet area."
United States
Paula
The price is NZ$306
includes taxes & fees
17 Nov - 18 Nov
TINY unit in cottage in the middle of Downtown
A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

19. 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, (2,228 reviews)
"Great stay Large comfortable.room Reasonable price"
United States
Martyn
The price is NZ$171
includes taxes & fees
22 Nov - 23 Nov
The View Hotel, Trademark Collection by Wyndham
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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Find holiday rentals that suit your style

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Top Winter Springs Hotel Reviews

A hotel with a modern design, featuring a pool area, outdoor seating, and a covered walkway.
Home2 Suites by Hilton Orlando Near UCF

Home2 Suites by Hilton Orlando Near UCF

Home2 Suites by Hilton Orlando Near UCF
Orlando

10/10 Excellent

Newest hotel in the UCF region. Great amenities, good breakfast, decent prices. Close to quite a few dining options
Australia
nick
Reviewed May 23, 2026
Home2 Suites by Hilton Orlando Near UCF

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 favorite 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 depends 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 NZ$137 per night. Entering your travel dates in the search wizard you might find 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.