Winter Springs Vacation Rentals

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Vacation Rentals in Winter Springs

Lobby sitting area
The View Studio Suites and Event Venue

Aparthotel in Orlando

3.0 star property
8.4 out of 10, Very Good, (1407)
"Nice breakfast, friendly staff, great location "
United States
Yessica
$75 nightly
The price is $84
Dec 1 - Dec 2
Total with taxes and fees
The View Studio Suites and Event Venue
Terrace/patio
The Point by Edge

Aparthotel in Florida Center

4.0 star property
8.4 out of 10, Very Good, (812)
"Great accommodations!"
United States
Champayne
$81 nightly
The price is $91
Nov 30 - Dec 1
Total with taxes and fees
The Point by Edge
Terrace/patio
The Front Porch

Apartment in Sanford

3.0 star property
10.0 out of 10, Exceptional, (2)
"What a great space. 2 big bedrooms, and a great front porch apace with a hammock to watch the sunrise. Quite street just blocks from the center of downtown Sanford. I've used their properties 8-10 tines and ive never been disappointed. "
United States
Patrick
$205 nightly
The price is $230
Dec 1 - Dec 2
Total with taxes and fees
The Front Porch
Terrace/patio
“NATURE IN THE CITY”

Mobile Home in Union Park

2.0 star property
9.0 out of 10, Wonderful, (6)
" Did not expect to be in someone’s back yard but overall was a pleasant stay. "
United States
Jola L.
$197 nightly
The price is $219
Nov 26 - Nov 27
Total with taxes and fees
“NATURE IN THE CITY”
Exterior
The Blue Aztec

Apartment in Sanford

3.0 star property
9.6 out of 10, Exceptional, (13)
"Great location! Great Dining! "
United States
Lisa
$219 nightly
The price is $236
Dec 10 - Dec 11
Total with taxes and fees
The Blue Aztec
The Club House | 2 bedrooms, individually decorated, individually furnished
Orlando Lakefront Tiny House Community

Cottage in Orlando

3.0 star property
9.4 out of 10, Exceptional, (331)
"We enjoyed our stay."
United States
Ardeeh
$151 nightly
The price is $169
Dec 7 - Dec 8
Total with taxes and fees
Orlando Lakefront Tiny House Community
Mini-fridge, microwave, cookware/dishes/utensils
Bella Breeze

Apartment in Sanford

2.5 star property
9.6 out of 10, Exceptional, (5)
"The place was clean, cozy, and well decorated, and the amenities were wonderful! The hosts have done a great job here."
United States
Courteny
$140 nightly
The price is $157
Dec 1 - Dec 2
Total with taxes and fees
Bella Breeze
1 bedroom, desk, iron/ironing board, free WiFi
Yania's Cozy Getaway

Apartment in Azalea Park

9.6 out of 10, Exceptional, (11)
"Clean quiet property. Perfect for studying. "
United States
Angela S.
$151 nightly
The price is $168
Nov 26 - Nov 27
Total with taxes and fees
Yania's Cozy Getaway
Outdoor dining
Traveler's Dream: Refresh & Recharge Poolside

Apartment in Casselberry

2.0 star property
9.4 out of 10, Exceptional, (6)
"In town for a work project and this was perfect for my needs. Quiet, clean, comfortable bed, plenty of space and hot shower to name a few. I would definitely recommend!"
United States
James R.
$128 nightly
The price is $140
Dec 1 - Dec 2
Total with taxes and fees
Traveler's Dream: Refresh & Recharge Poolside
Property grounds
COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community

Apartment in Deltona

2.0 star property
9.6 out of 10, Exceptional, (4)
"Loved the proximity to the wonderful bike and walking trail!"
United States
Sharon H.
$260 nightly
The price is $289
Dec 1 - Dec 2
Total with taxes and fees
COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community
Reception
Florida Hotel & Conference Center in the Florida Mall

Aparthotel in Orlando

3.5 star property
9.2 out of 10, Wonderful, (2264)
"Clean fresh smelling room, real friendly staff, great atmosphere. Always love staying here"
United States
Alexander
$168 nightly
The price is $190
Dec 11 - Dec 12
Total with taxes and fees
Florida Hotel & Conference Center in the Florida Mall
Interior
Charming 2-bedroom apartment in house with AC, WiFi included

Vacation Home in Apopka

10.0 out of 10, Exceptional, (9)
"It was quiet, clean and had snacks and drinks for us."
United States
Lori
$145 nightly
The price is $161
Nov 30 - Dec 1
Total with taxes and fees
Charming 2-bedroom apartment in house with AC, WiFi included
2 bedrooms, iron/ironing board, WiFi, bed sheets
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Apartment in Orlando

10.0 out of 10, Exceptional, (5)
"Great host, and stayed connected with us."
United States
Christopher
$232 nightly
The price is $258
Nov 28 - Nov 29
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Exterior
Totally 80's

Apartment in Sanford

3.0 star property
9.4 out of 10, Exceptional, (3)
"Cute, clean, and comfortable. Located in a safe neighborhood, the house had everything we needed for a great stay. Communication was timely and smooth—highly recommend."
United States
Serge
$140 nightly
The price is $157
Nov 30 - Dec 1
Total with taxes and fees
Totally 80's
Exterior
The Jazz Loft

Apartment in Sanford

3.0 star property
7.6 out of 10, Good, (5)
"The loft was very cool and unique. Loved it. I will definitely book this again."
United States
sherri
$135 nightly
The price is $151
Dec 1 - Dec 2
Total with taxes and fees
The Jazz Loft
Interior
King Bed - Fire Pit - Private - Grill - Location

Apartment in Orlando

10.0 out of 10, Exceptional, (6)
"Great place! We loved it!"
United States
Sheri
$236 nightly
The price is $263
Dec 9 - Dec 10
Total with taxes and fees
King Bed - Fire Pit - Private - Grill - Location
Private kitchen
Charming Caribbean 1-bedroom roomy Apartment in amazing Downtown Sanford

Apartment in Sanford

2.0 star property
9.6 out of 10, Exceptional, (4)
"Clean, close to downtown restaurant and sights. Was a work trip and host helped my wife set up her work computer which was much appreciated. Just a great place to stay for short term."
United States
Frank F.
$260 nightly
The price is $288
Dec 3 - Dec 4
Total with taxes and fees
Charming Caribbean 1-bedroom roomy Apartment in amazing Downtown Sanford
1 bedroom, desk, WiFi, bed sheets
The Sanford Foodie Guest House

Cottage in Sanford

8.8 out of 10, Excellent, (13)
"Cozy little place to stay"
United States
Ruth P.
$128 nightly
The price is $141
Nov 30 - Dec 1
Total with taxes and fees
The Sanford Foodie Guest House
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services
Boho Nights

Apartment in Sanford

3.0 star property
8.8 out of 10, Excellent, (6)
"Wonderful spot, and excellent hosts!"
United States
Thomas
$140 nightly
The price is $157
Dec 2 - Dec 3
Total with taxes and fees
Boho Nights
Dining
Orlando 2BR Apt, Full Kitchen, Near Epic Universe

Apartment in International Drive District

10.0 out of 10, Exceptional, (2)
"Our stay was amazing here! We felt like we were on Love Island haha with how it looked. It was clean and close to a lot of places that we enjoy going too. Definitely a great stay for anyone with a group looking to have some fun!"
United States
Carlos O.
$251 nightly
The price is $279
Dec 1 - Dec 2
Total with taxes and fees
Orlando 2BR Apt, Full Kitchen, Near Epic Universe
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

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Na"
Liz 2-night trip
Posted 7 hours ago
Rosen Inn at Pointe Orlando

Find out more about Winter Springs

Everything you need to know about Winter Springs vacation rentals

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

Winter Springs vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winter Springs in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $84 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Springs rentals

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

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.

Explore a world of travel with Expedia

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.

What are some of the best vacation home rentals that Winter Springs has to offer?

Vista Cay Resort by Casiola Vacation Homes: Visitors like this Winter Springs vacation home rental. It is located on a lake and has a private balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop. It offers a garden, an arcade game room, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Winter Springs?

Expedia has 8 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 Kia Center and Camping World Stadium.

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.