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Winter Springs Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winter Springs holiday rentals

Outdoor pool

1. Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone

Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Lake Mary
9.8 out of 10, Exceptional, (63 reviews)
"Everything was great as usual!!"
United States
Christine B.
The price is HK$883
HK$2,111 total
includes taxes & fees
17 Aug - 18 Aug
Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Smart TV, fireplace, video games

2. Early Check In Lake Mary Last-Minute Deal!

Early Check In Lake Mary Last-Minute Deal!
Lake Mary
10.0 out of 10, Exceptional, (20 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is HK$699
HK$1,827 total
includes taxes & fees
17 Aug - 18 Aug
Early Check In Lake Mary Last-Minute Deal!
3 bedrooms, desk, iron/ironing board, free WiFi

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, (54 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is HK$1,024
HK$1,990 total
includes taxes & fees
17 Aug - 18 Aug
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Coffee/tea maker, fridge, microwave, oven

4. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, Exceptional, (46 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
The price is HK$847
HK$2,558 total
includes taxes & fees
15 Sept - 16 Sept
Florida Vacation with pool fun for families
Property grounds

5. Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
The price is HK$1,075
HK$2,766 total
includes taxes & fees
1 Sept - 2 Sept
Incredible Private Lakefront Cottage Retreat
Living area

6. 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 HK$516
HK$1,105 total
includes taxes & fees
17 Aug - 18 Aug
Boho Nights
Coffee/tea maker, fridge, microwave, oven

7. Home Sweet Home

Home Sweet Home
Sanford
9.4 out of 10, Exceptional, (33 reviews)
"The house was perfect for our three night stay. The location was a short distance to all our activities. It was super clean and had very nice updates. The area was quiet and the house very comfortable. If we are in the area again, we’ll definitely stay there again!"
United States
Janice M.
The price is HK$530
HK$2,442 total
includes taxes & fees
17 Aug - 18 Aug
Home Sweet Home
Interior

8. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.6 out of 10, Exceptional, (20 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 HK$600
HK$1,200 total
includes taxes & fees
18 Aug - 19 Aug
Bella Breeze
Coffee/tea maker, fridge, microwave, paper towels

9. Chic Studio -10 Min to SFB Airport & Boombah Sports Complex

Chic Studio -10 Min to SFB Airport & Boombah Sports Complex
Sanford
10.0 out of 10, Exceptional, (8 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 HK$700
HK$941 total
includes taxes & fees
15 Sept - 16 Sept
Chic Studio -10 Min to SFB Airport & Boombah Sports Complex
Dining

10. River City Retreat

River City Retreat
Sanford
9.6 out of 10, Exceptional, (20 reviews)
"Great place and quick, simple check in."
United States
Dennis L.
The price is HK$953
HK$1,696 total
includes taxes & fees
22 Aug - 23 Aug
River City Retreat
Living area

11. The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (14 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is HK$600
HK$1,788 total
includes taxes & fees
17 Aug - 18 Aug
The Blue Aztec
Exterior

12. 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 HK$565
HK$1,160 total
includes taxes & fees
17 Aug - 18 Aug
The Jazz Loft
Terrace/patio

13. 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 HK$667
HK$1,375 total
includes taxes & fees
17 Aug - 18 Aug
The Blue Aztec
3 bedrooms, desk, iron/ironing board, WiFi

14. 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 home! My friends and I had such an amazing time and I loved the dog bed & bowls for my dog Venus who stayed with us"
United States
Janelle G.
The price is HK$918
HK$2,896 total
includes taxes & fees
18 Aug - 19 Aug
Tranquil 3-bedroom house in Sanford with AC, WiFi
2 bedrooms, desk, free WiFi

15. 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 HK$989
HK$1,767 total
includes taxes & fees
17 Aug - 18 Aug
The Front Porch
2 bedrooms, iron/ironing board, WiFi, bed sheets

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

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
9.8 out of 10, Exceptional, (12 reviews)
"Very clean and hospitable. Recommend staying here for sure!"
United States
Kyle Y.
The price is HK$824
HK$2,045 total
includes taxes & fees
17 Aug - 18 Aug
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Desk, WiFi, bed sheets

17. Studio in the heart of Orlando

Studio in the heart of Orlando
Azalea Park
9.4 out of 10, Exceptional, (6 reviews)
"Can’t complain. Would re book for sure."
United States
Matthew
The price is HK$373
HK$1,236 total
includes taxes & fees
17 Aug - 18 Aug
Studio in the heart of Orlando
Exterior detail

18. Downtown Cottage

Downtown Cottage
Colonialtown North
8.6 out of 10, Excellent, (13 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is HK$467
HK$1,344 total
includes taxes & fees
26 Aug - 27 Aug
Downtown Cottage
1 bedroom, desk, iron/ironing board, free WiFi

19. Private guest studio in the heart of orlando.

Private guest studio in the heart of orlando.
Orlando
9.8 out of 10, Exceptional, (63 reviews)
"Super clean and updated, loved the location, and quiet neighborhood. Definitely will stay here again!"
United States
Gianna N.
The price is HK$487
HK$1,032 total
includes taxes & fees
17 Aug - 18 Aug
Private guest studio in the heart of orlando.
1 bedroom, desk, iron/ironing board, free WiFi

20. Yania's Cozy Getaway

Yania's Cozy Getaway
Azalea Park
9.8 out of 10, Exceptional, (16 reviews)
"Just what we needed for our quick trip to Orlando! super communicative host and very nice area. Would love to stay here again if given the chance!"
United States
Liv B.
The price is HK$530
HK$1,371 total
includes taxes & fees
18 Aug - 19 Aug
Yania's Cozy Getaway
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

Universal’s Loews Portofino Bay Hotel

Universal’s Loews Portofino Bay Hotel

10/10 Excellent
"I loved how quiet the rooms were. I couldn't hear doors shutting, kids screaming or people in the halls. It was great. The express passes were amazing, and it's the only way to go when visiting the parks. My only complaint was that our room wasn't ready by 4pm, but the staff was friendly and helpful to"
Shawn 3-night trip
Posted 11 hours ago
Universal’s Loews Portofino Bay Hotel
Coco Key Hotel & Water Park Resort

Coco Key Hotel & Water Park Resort

10/10 Excellent
"Good"
Janeska N. 3-night trip
Posted 13 hours ago
Coco Key Hotel & Water Park Resort

Find out more about Winter Springs

Search for holiday rentals in Winter Springs on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter Springs using one of the methods below:

  • View our selection of featured holiday rentals in Winter Springs
  • Use the map to find apartments and other holiday homes in the Winter Springs neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter Springs while they last

Look no further and take a look at our great range of rental properties in Winter Springs!

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.