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Winter Springs Vacation Rentals

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winter Springs vacation rentals

Interior

1. 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 P4,721
P9,434 total
includes taxes & fees
Aug 27 - Aug 28
Bella Breeze
WiFi (free)

2. Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is P4,499
P9,667 total
includes taxes & fees
Aug 30 - Aug 31
Cozy Modern Studio
Exterior

3. 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 P4,443
P9,123 total
includes taxes & fees
Sep 21 - Sep 22
The Jazz Loft
2 bedrooms, desk, WiFi (free)

4. 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 P7,775
P13,892 total
includes taxes & fees
Aug 26 - Aug 27
The Front Porch
Living area

5. 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 P4,721
P9,434 total
includes taxes & fees
Aug 30 - Aug 31
Boho Nights
Living area

6. 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 P4,721
P14,062 total
includes taxes & fees
Sep 10 - Sep 11
The Blue Aztec
Living area

7. The Mellow Yellow

The Mellow Yellow
3.0 star property
Downtown Sanford
6.0 out of 10, (3 reviews)
"Owners had over booked this property, but proactively reached out and moved me to like property, BoHo Nights. Very nice place. Easy walk to downtown Sanford. Coffee options provided were appreciated."
United States
Gary
The price is P4,332
P13,628 total
includes taxes & fees
Aug 30 - Aug 31
The Mellow Yellow
Exterior

8. The Contemporary

The Contemporary
3.0 star property
Downtown Sanford
The price is P7,775
P17,484 total
includes taxes & fees
Sep 24 - Sep 25
The Contemporary
Courtyard

9. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very Good, (327 reviews)
"So confusing, the online booking experience. Was confusing"
United States
Edward
The price is P6,397
P7,196 total
includes taxes & fees
Aug 26 - Aug 27
Suites by The Wellborn
2 bedrooms, high-speed internet

10. Upstay 2BR Golfer s Retreat w Patio Ventura Resort

Upstay 2BR Golfer s Retreat w Patio Ventura Resort
2.0 star property
Ventura
The price is P5,057
P15,093 total
includes taxes & fees
Sep 8 - Sep 9
Upstay 2BR Golfer s Retreat w Patio Ventura Resort
Terrace/patio

11. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.4 out of 10, Very Good, (1,246 reviews)
"Amazing location and price and quality"
United States
Ashlee
The price is P3,703
P4,929 total
includes taxes & fees
Aug 26 - Aug 27
The Point Hotel & Suites Orlando
Private kitchen

12. Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
4.0 star property
Downtown Orlando
10.0 out of 10, Exceptional, (1 review)
"Very nice place"
United States
John
The price is P6,109
P24,044 total
includes taxes & fees
Aug 31 - Sep 1
Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
Property amenity

13. Landing Apartments Orlando - Central Business District

Landing Apartments Orlando - Central Business District
4.0 star property
Downtown Orlando
8.0 out of 10, Very Good, (2 reviews)
"The idea of the landing is great but the building needs to do a better job with cleaning and maintenance the apartment better. . The place wasn’t the cleanest , a roach came from behind the stove while cooking , its holes in the doors , the shower makes a weird noise as if water is going to gush out at any moment, one of the window don’t completely close so you can hear all the outside noise . . overall the place is okay. . Keel in mind it is downtown Orlando next to a bus terminal so sleep is...
United States
Nikitress
The price is P6,178
P18,059 total
includes taxes & fees
Aug 26 - Aug 27
Landing Apartments Orlando - Central Business District
WiFi (free), bed sheets

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, (2,127 reviews)
"We had a really nice stay! The room was great and very comfortable, the breakfast was delicious, and the staff was incredibly friendly and helpful."
United States
Alvaro Andres
The price is P5,221
P5,874 total
includes taxes & fees
Aug 26 - Aug 27
The View Hotel, Trademark Collection by Wyndham
Interior

15. Upstay Golfer's Retreat w Patio at Ventura Resort

Upstay Golfer's Retreat w Patio at Ventura Resort
3.5 star property
Ventura
The price is P4,381
P13,885 total
includes taxes & fees
Sep 8 - Sep 9
Upstay Golfer's Retreat w Patio at Ventura Resort
Property grounds

16. Sunny Stays

Sunny Stays
2.0 star property
Oak Ridge
The price is P6,665
P17,371 total
includes taxes & fees
Sep 8 - Sep 9
Sunny Stays
Living area

17. Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
4.0 star property
Kirkman North
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
Private kitchen

18. Century Millenia

Century Millenia
3.0 star property
Florida Center
9.0 out of 10, Wonderful, (144 reviews)
"Absolutely amazing and perfect will be back here everytime!"
United States
Arianna
The price is P5,314
P10,606 total
includes taxes & fees
Sep 1 - Sep 2
Century Millenia
Living area

19. Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning

Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
3.5 star property
Colonialtown South
The price is P17,829
P24,275 total
includes taxes & fees
Aug 27 - Aug 28
Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
2 bedrooms, high-speed internet

20. Luxury House - Sleeps 8 Golf Disney Family Fun

Luxury House - Sleeps 8 Golf Disney Family Fun
2.0 star property
Ventura
8.0 out of 10, Very Good, (1 review)
The price is P7,055
P29,397 total
includes taxes & fees
Sep 8 - Sep 9
Luxury House - Sleeps 8 Golf Disney Family Fun
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
"Amazing hotel with a lovely boat ride to the parks each day. Express park with hotel is a great touch."
James 2-night trip
Posted less than an hour ago
Universal’s Loews Portofino Bay Hotel

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 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.

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.