Winter Springs Holiday Rentals from €73: Search Short-Term Rentals

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Our top choices for Winter Springs holiday rentals

A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

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

Casselberry

Kevin K.

includes taxes & fees

12 Oct - 13 Oct

2. Florida Vacation with pool fun for families

Casselberry

Daniel W.

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

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

Lake Mary

Colette T.

includes taxes & fees

13 Oct - 14 Oct

A modern kitchen with white cabinets, a microwave, and a green wall with a neon sign.

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

Lake Mary

Tricia S.

includes taxes & fees

15 Oct - 16 Oct

A swimming pool with lounge chairs and palm trees.

5. The Point Hotel & Suites Orlando

Florida Center

Lisa

includes taxes & fees

25 Oct - 26 Oct

A modern living room with a flat-screen TV on a wooden cabinet, two black round tables, a brown rug, a chair, and a lamp.

6. Suites by The Wellborn

Lake Cherokee

Dustin

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with a marble countertop, gold faucets, and a large window.

7. Bella Breeze

Downtown Sanford

Sara

includes taxes & fees

11 Oct - 12 Oct

A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

8. The View Hotel, Trademark Collection by Wyndham

Orlando

Breila

includes taxes & fees

19 Oct - 20 Oct

A compact workspace with a laptop, a desk lamp, a notebook, and a cup.

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

Sanford

Julia F.

includes taxes & fees

11 Oct - 12 Oct

A compact living space with a kitchenette, a dining area, and a seating area with a couch and chairs.

10. The Blue Aztec

Downtown Sanford

Lisa

includes taxes & fees

11 Oct - 12 Oct

A modern kitchen with light-colored cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

11. Home Sweet Home

Sanford

Janice M.

includes taxes & fees

19 Oct - 20 Oct

A vibrant living room with a teal sofa, a wooden chair, and a coffee table.

12. Boho Nights

Downtown Sanford

Nicholas

includes taxes & fees

12 Oct - 13 Oct

A bedroom with a bed, a ceiling fan, a nightstand, a lamp, a door, and a painting on the wall.

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

Orlando

Kyle Y.

includes taxes & fees

11 Oct - 12 Oct

A backyard with a hammock, outdoor seating, and string lights.

14. The Jazz Loft

Downtown Sanford

Tiffany

includes taxes & fees

11 Oct - 12 Oct

A modern kitchen with dark cabinets, a stainless steel refrigerator, and a dining area with a glass table and white chairs.

15. River City Retreat

Sanford

Dennis L.

includes taxes & fees

17 Oct - 18 Oct

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.

16. The Front Porch

Downtown Sanford

Johnny

includes taxes & fees

11 Oct - 12 Oct

A neatly made bed with white linens and towels, a dark door, and two framed artworks on the wall.

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

Sanford

Rodney

includes taxes & fees

12 Oct - 13 Oct

18. The Blue Aztec

Downtown Sanford

Kael

includes taxes & fees

11 Oct - 12 Oct

A modern kitchen with a dining area, a black sofa, and a painting of a sunset.

19. Cozy studio in fabulous Orlando close to everything

Orlando

Kristen a.

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a bed, a ceiling fan, and artwork on the walls.

20. Downtown Private Efficiency Lake Eola Central Business District

Downtown Orlando

James P.

includes taxes & fees

19 Oct - 20 Oct

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Top Winter Springs Hotel Reviews

Universal's Endless Summer Resort - Dockside Inn and Suites

8/10 Good

"A large resort where people bring lots of small children so it can get loud at times anywhere on the property, hallways and rooms. Our floor was quiet thankfully. The staff at check in was a little snappy and short, but everyone else was nice. The pool was closed on a Saturday when there due to rain. I would stay here again bc of the room and laundry. But if you don’t like lots of people and noise, then not for you. Shuttle to and from was a great amenity and early entry."

Universal's Endless Summer Resort - Surfside Inn and Suites

10/10 Excellent

"Better than Disney! Hands down better staff, better amenities, cleaner areas. Last time we stayed at Animation at Disney garbage cans were overflowing, food left outside doors for over a day. Surfside, was amazing! Completely different, comfortable, friendly and impeccable pool experience! Can't wait to go back! The staff were beyond professional."

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, apart-hotels, 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 €73 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.

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Check prices for these dates

Our top choices for Winter Springs holiday rentals

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

2. Florida Vacation with pool fun for families

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