Are there vacation rentals with a dedicated workspace in Winter Springs?

Yes! Work meets play with ease at over 30 vacation rentals in Winter Springs featuring dedicated workspaces. Stay connected and productive in your home away from home.

Are there pet-friendly vacation rentals in Winter Springs?

Four-legged friends are welcome in Winter Springs. Choose from more than 20 vacation rentals for guests traveling with pets.

Are there Winter Springs vacation rentals on Airbnb with pools?

Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Winter Springs, available on Airbnb. Make a splash and soak up the sun in style!

How much does it cost to stay in house rentals in Winter Springs?

Experience the best of Winter Springs with our house rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Do house rentals in Winter Springs have wireless internet?

Absolutely! We offer over 40 house rentals with wireless internet in Winter Springs. Enjoy a tailored experience with all the comforts you desire.

Are there family-friendly house rentals in Winter Springs?

Winter Springs has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Do house rentals in Winter Springs have air conditioning?

Absolutely! We offer over 40 house rentals with air conditioning in Winter Springs. Enjoy a tailored experience with all the comforts you desire.

What are the most popular amenities for House Rentals in Winter Springs?

Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with air conditioning, over 40 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Winter Springs vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Winter Springs

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in Kissimmee

4.81 out of 5 average rating, 21 reviews

Florida Retreat 3BR Resort Cottage near WDW

- Experience ultimate comfort at the Margaritaville Resort 3BR Cottage in Kissimmee. - Only minutes from Walt Disney World and a short drive to Universal Studios and other attractions in Central Florida. - Enjoy a spacious living area with a well-equipped kitchen, comfortable bedrooms, smart TVs and high-speed free Wi-Fi. - Relax on the outdoor patio or take advantage of free parking. This vacation home is perfect for creating unforgettable memories with easy access to all the area's highlights.

Guest favorite

Townhouse in Kissimmee

4.8 out of 5 average rating, 246 reviews

#5708 LakeFront, Two Master, Jacuzzi, Pool, Disney

Stunning LAKEFRONT view with SOUTH exposure for all day SUNLIGHT. MODERN furniture & HARDWOOD floors! Private JACCUZI! 5 SMART TVs & FREE WIFI. 4 BDS (2 with ensuite, one on each floor) & 3.5 BATH. SS appliances, water filter and quartz counter tops. 10 mins to Disney, 15 mins to Sea World, 20 mins to Universal. Walk to Old Town, Fun Spot, restaurants and stores. Uber/Lyft/Lynx bus to Disney. Resort heated pool, water slides, fitness, tennis, restaurant/bar, mini store and 24/7 gate with guard.

Guest favorite

Home in Kissimmee

5 out of 5 average rating, 17 reviews

My Disney Villa

Looking for the ultimate vacation spot near Disney Orlando and Epcot? Look no further! Our newly renovated large 5-bedroom Airbnb is just a genuine 12-minute drive away from these amazing parks, Our home features 2 amazing themed rooms, including a state-of-the-art Star Wars and Mickey Mouse rooms that will surely make your kids feel like they're in their own magical world. We also have 3 large adult rooms, each equipped with comfortable beds, a huge pool area with new furniture, 2 dining areas

Guest favorite

Condo in Kissimmee

4.91 out of 5 average rating, 46 reviews

Perfect Kissimmee Kondo with Jacuzzi!

Wonderfully Furnished Vacation Townhome with Private Hot Tub in gated Encantada Resort Community! The delightful open plan, just minutes from all parks, features ceramic tile flooring throughout downstairs & a modern gray/orange decor that'll provide a great place for you to relax while you're enjoying all that central Florida has to offer! Enjoy a beach entry pool, lap pool, hot tub, fitness center, playground, business center, and restaurant . Check out the tour: https://youtu.be/0QA3Z-MHKLM

Superhost

Home in Kissimmee

4.89 out of 5 average rating, 53 reviews

Baby Safe w *Indoor PlayGround*

*Free POOL HEAT*Close to Disney Parks! Home equipped for baby! Full nursery, double stroller, highchair, packnplay, outlet covers, baby gates, toys, books, bouncy, and more. Kids love the Toy Story indoor playground with ball-pit, trampoline & slide, the fun doesn't stop at Disney! 6 themed bedrooms (3 Kids & 3 Adult themes), 5 baths, appliance stocked kitchen, a movie/game loft w/ 2 queen sofa sleepers, in-ground pool and Jacuzzi with BABY GATE! Fully furnished high-end patio and pool area.

Superhost

Home in Kissimmee

4.69 out of 5 average rating, 16 reviews

Cozy VacationHome - Disney Parks

Have fun with the whole family at this comfortable and spacious townhome, take advantage of the full amenities that come with it. This space is great for both short and long stays and excellent for family visits. Close to Disney & more Orlando Areas *18 min or 11 miles to Disney Area *26 min or 17 miles to SeaWorld *30 min or 21 miles to Universal *40 min or 34 miles to MCO International Airport Orlando *50 min or 29 miles to Legoland *1h 15 min to Tampa Beach *1h 30 min to Melbourne Beach

Guest favorite

Home in Kissimmee

5 out of 5 average rating, 18 reviews

Disney Vacations Oasis

Experience the best of Disney's area with the comfort and luxury of our home. Whether you're here for adventure or relaxation, we provide everything you need for an unforgettable stay. We prioritize your health and safety. Our home undergoes a thorough professional cleaning and sanitization process prior to your arrival, ensuring every surface is spotless and ready for you to enjoy. Great amenities, including lazy river, restaurant, bar, gym and everything you may need during your stay.

Guest favorite

Villa in Kissimmee

4.81 out of 5 average rating, 63 reviews

Home w/ PVT Pool, Game Room & Resort access 2100

Our luxurious 5-bedroom, 5.5-bathroom home boasts a spacious living room with Smart TV, a fully-equipped kitchen and dining room, a cozy upstairs living area perfect for movie nights as well as an air-conditioned game room featuring a pool table and air hockey. Venture to the backyard to find even more amazing features such as a spacious private pool and SPA, sun loungers, a barbecue and a table with 6 seats where you and your guests will be able to enjoy some sun-filled al fresco dining.

Guest favorite

Home in Osceola County

4.8 out of 5 average rating, 5 reviews

Family vacation house near Disney! - 7105

Imagine this cozy getaway in a lush gated community, just a stone's throw away from the magic of Disney. This vacation home boasts four thematic bedrooms, perfect for hosting your family and friends. Step into the clubhouse, with an amazing bakery. It's the ideal spot for unwinding after a day of adventure in the nearby theme parks. With its welcoming atmosphere and convenient location, this retreat offers the perfect blend of relaxation and excitement for your dream vacation. Book now!

Guest favorite

Condo in Kissimmee

4.95 out of 5 average rating, 155 reviews

*Sunset Perch: Views, Reunion Resort, XBox, 2Pools

This modern 3-bedroom luxury condo (with an ELEVATOR right to the door) has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

Superhost

Apartment in Kissimmee

4.86 out of 5 average rating, 224 reviews

Modern Great Villa near Disney & Parks

This place is 5 up to 20 minutes to all of orlando's amusement and water parks!. One of the best units in this resort, just book and see for yourself. An excellent unit with great reviews. There is an awsome pool and jacuzzi onsite (Please note, sometimes the jacuzzi breaks down and may not work during your stay). high speed wifi. easy smooth self checkin with a private keypad code that is being replaced between each new guest, walking distance to many shops and plazas, free parking.

Superhost

Home in Orlando

4.88 out of 5 average rating, 8 reviews

PuraVida Urban Lakehouse+Bungalow - Full Property

Welcome to our Pura Vida jungle-inspired urban lake house, nestled in the heart of Orlando! Combining tropical tranquility with modern luxury, this unique retreat offers the perfect escape for travelers seeking a serene atmosphere just minutes from the city's attractions. **NO PARTY OF ANY KIND OR EVENT ALLOWED** Circular driveway makes for free and easy parking. Located 15 min from the airport, 15 min to Universal, 30 min to Disney, and 50 min to Cocoa Beach.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winter Springs vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Winter Springs's top sights

Rock & Brews76 locals recommend

Black Hammock Orlando Airboat Rides26 locals recommend

Black Hammock Restaurant18 locals recommend

Oviedo Mall16 locals recommend

Sushi Pop Restaurant16 locals recommend

Townhouse Restaurant15 locals recommend

Other great vacation rentals in Winter Springs

Superhost

Home in Kissimmee

4.8 out of 5 average rating, 5 reviews

Cute Vacation Home Very Close to Disney

Superhost

Home in Davenport

4.75 out of 5 average rating, 65 reviews

Holiday home

Guest favorite

Condo in Kissimmee

4.76 out of 5 average rating, 89 reviews

Waterview Condo Close to Disney

Guest favorite

Home in Davenport

5 out of 5 average rating, 5 reviews

New! Windsor Island Resort with pool by Disney 03

Guest favorite

Townhouse in Kissimmee

4.94 out of 5 average rating, 185 reviews

Beautiful family home near all attractions.

Superhost

Home in Kissimmee

4.68 out of 5 average rating, 22 reviews

Vacation Home with Pool & Spa near Disney

Guest favorite

Home in Kissimmee

5 out of 5 average rating, 7 reviews

Lovely home away from home!

Superhost

Home in Four Corners

4.85 out of 5 average rating, 13 reviews

DisneyVacationHomeLazyRiver9021

Show all

Quick stats about vacation rentals in Winter Springs

Total rentals
80 properties
Nightly prices starting at
G$4,178 GYD before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
20 properties have a pool

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Winter Springs?
Yes! Work meets play with ease at over 30 vacation rentals in Winter Springs featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winter Springs?
Four-legged friends are welcome in Winter Springs. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there Winter Springs vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Winter Springs, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in house rentals in Winter Springs?
Experience the best of Winter Springs with our house rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Winter Springs have wireless internet?
Absolutely! We offer over 40 house rentals with wireless internet in Winter Springs. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winter Springs?
Winter Springs has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Winter Springs have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Winter Springs. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Winter Springs?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with air conditioning, over 40 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Winter Springs vacation rentals

Top-rated vacation rentals in Winter Springs

Cottage in Kissimmee

Townhouse in Kissimmee

Home in Kissimmee

Condo in Kissimmee

Home in Kissimmee

Home in Kissimmee

Home in Kissimmee

Villa in Kissimmee

Home in Osceola County

Condo in Kissimmee

Apartment in Kissimmee

Home in Orlando

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Winter Springs vacation rentals

Stay near Winter Springs's top sights

Other great vacation rentals in Winter Springs

Home in Kissimmee

Home in Davenport

Condo in Kissimmee

Home in Davenport

Townhouse in Kissimmee

Home in Kissimmee

Home in Kissimmee

Home in Four Corners

Quick stats about vacation rentals in Winter Springs

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with a pool

Frequently Asked Questions

Destinations to explore