
Vacation rentals in Winter Springs
Find and book unique accommodations on Airbnb
Quick stats about vacation rentals in Winter Springs

Total vacation rentals
Explore 90 vacation rentals in Winter Springs

Nightly prices starting at
Winter Springs vacation rentals start at ﺩ.ﺇ 73 per night before taxes and fees

Verified guest reviews
Over 4,050 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
90 of Winter Springs vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Winter Springs rentals

4.8 Average rating
Winter Springs stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated vacation rentals in Winter Springs
Guests agree: these stays are highly rated for location, cleanliness, and more.

Farmhouse-Chic Retreat with a Charming Patio
Guests have full use of the house, including a spacious kitchen. Four bedrooms with memory foam mattresses ensure you can sleep comfortably. The dining room table can seat 6-8. In the living room there’s a comfortable seating area across the room from a large desk - great for those traveling for work! There is a separate laundry room off the back patio. Guests will have complimentary use of detergent. Iron and ironing board are also available for guest use. On the property there’s an occupied mother-in-law apartment - with separate parking and it’s own entrance so that guests staying in the house are not disturbed by the apartment’s full-time occupant. The backyard is also has a dividing fence for house guests’ privacy. As a guest staying at the house you will have privacy, but I’m local nearby and can assist guests at their request. Behind the house is an occupied apartment that has its own entrance, parking, and backyard. Nestled into a cluster of moss-draped oaks, the house is only a short drive from restaurants and shops in Lake Mary and quaint downtown Sanford. The best way to navigate the area is by car. There are several car rental agencies nearby, with the Orlando-Sanford International Airport just 5-7 min drive.

Oviedo Oasis:2/1 attached Guest Suite;Private Pool
Cozy 2 bedroom guest suite (700 sq ft) connected to host's primary residence but has its own entrance and there is no shared spaces inside. Living room, 2 separate bedrooms and a full size shower. Amenities include a coffee bar, mini fridge, microwave, TV, Wifi and access to non-heated swimming pool. Host primary residence does overlook the pool area. Listing does not include a full kitchen. Central to everything: UCF: 5 miles MCO Airport: 25 miles Sanford Airport: 11 miles Disney: 40 miles

Treehouse at Danville
Private Getaway seen on Netflix' Most Amazing Vacation Rentals! Fulfill your dream of staying in a tree house! For safety reasons, this venue is for adults only. We do not allow children or pets. The Treehouse has a tree trunk elevator, private shower, air-conditioning, and real toilet inside so that you can bring your significant other(no compost toilet here). This 18 foot yurt has accent lighting to create the mood of living in the trees on a starry night. Danville is a glamping experience.

Maitland-Orlando Area, FL. Pool House Bungalow
Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

"Winnie's Place" A Peaceful Guesthouse with Pool.
Share the quiet yard and pool with hosts. 1 hr. from Disney & the beaches. 12 yr & older only. Single Sofa bed for 3rd guest. NOT a heated pool. Not Handicap Certified, but most wheelchair guests have not had issues. Narrowest opening 32" Ramp into unit by pool. Shower no steps. Queen bed height 29"-standard cabinets. Grab bars in bathroom. Airbnb's Accessibility Policy has exempted this listing from accepting Service & Emotional Support Animals due to owner's severe health condition.

Charming Private Lakefront Cottage Retreat
You can fully relax in this adorable lakefront cottage. We're sure you'll enjoy all of the wonderful amenities this peaceful property has to offer. Our incredibly unique cottage is nestled under a large grand oak tree and tucked away behind climbing jasmine vine clad fencing and security gates. Inside, you will find a new remodeled fully stocked kitchen and luxury bathroom. Our cozy cottage has all the comforts of home and more. Reserve your stay today and enjoy this special property.

Relaxing 3-Bedroom Pool Getaway
This is a 3-bedroom 2-bath home, bathroom in the main bedroom connects directly to the pool. Accommodates comfortably up to 6 people. We have a wide range of amenities including wifi, TV, covered pool, fully equipped kitchen, and more! This is located in a quiet neighborhood located 30 minutes from Universal Studios, Sea World, and Disney World. The home comes with pool toys, board games, a space for an outdoor bar! The outdoor space is enclosed to keep out mosquitos and other pests.

Pvt Fishing lk , Pets,Nature, Pool,garage
No HOA. Private 20 acre lake property, with fishing boats and trolling motors, canoes , peaceful boardwalk / dock. Large extra parking for trailers or work trucks. Fishing gear / poles. 2 car garage for safely storing whatever you bring. Fishing gear, tools, bikes, Harley's. Located near Seminole Trail, parks, sun-rail station. 45-60 min from the beach or the attractions DISNEY, UNIVERSAL STUDIOS, close to Lake Mary, Sanford, Wekiva Springs, Daytona 500, Bike week, 20 min from Boombah

Stylish & spa like Getaway - peaceful garden suite
Relax and unwind from your busy life in this serene and quiet getaway. We are located 5 minutes to shopping and dining in downtown Lake Mary in a beautiful and safe neighborhood. Enjoy the solar heated saltwater pool and the comfy outdoor lounge area, Enjoy the backyard with its mature trees and tropical flowers. The indoors come with a luxury and modern wellness bathroom. Soak in the oversized jetted tub or reenergize in the stylish rainfall shower with inbuilt bench and mood lighting.

Sunset Cottage in Lake Mary, Florida
Located on beautiful Lake Mary, this completely renovated studio sized guest house offers beautiful sunsets over the lake from a private patio. A comfortable queen bed, stylish sitting area and fully stocked kitchenette make for a wonderful stay in the Lake Mary- Sanford area. Minutes from the Sanford airport, close to the Sunrail station and 45 minutes to either Disney World or the beach. Our guest cottage is a perfect place to visit. Please note: The cottage is lakeview only.

TreeHouse in the Cloud, (Close toTheme Parks
The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

The Cypress House
This beautiful 2 bedroom, 1 bathroom Ranch Style home is conveniently located 3.5 miles from the Sanford International Airport and Boombah Sports Complex. The inviting landscape and backyard where you can cool off in the rustic style stock tank pool or grill out and relax on the patio. The open floor plan creates a spacious feel and every finish was selected with care. For a glamping experience check out our other listing: https://abnb.me/z3XrgOSPNFb
Popular amenities for Winter Springs vacation rentals
Other great vacation rentals in Winter Springs

The Springs -Townhouse in the Winter Springs

Pool House Paradise-Walk to Downtown Lake Mary

Moxy Luxe Vacation /Heated Pool /Last-Minute Deals

2BR Home in Heart of Longwood

Oviedo Home Near UCF & Orlando | Sleeps 8

Luxury Villa: Heated Pool · Disney & Epic Universe

Harmony

Entire Townhome | Stylish & Cozy | Peaceful
When is the best time to visit Winter Springs?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 455 | ﺩ.ﺇ 455 | ﺩ.ﺇ 367 | ﺩ.ﺇ 481 | ﺩ.ﺇ 477 | ﺩ.ﺇ 466 | ﺩ.ﺇ 430 | ﺩ.ﺇ 441 | ﺩ.ﺇ 393 | ﺩ.ﺇ 444 | ﺩ.ﺇ 514 | ﺩ.ﺇ 481 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Frequently Asked Questions
What are the best places to stay in Winter Springs?
Accommodations are frequently found in residential neighborhoods near parks and greenways, and many are popular with families. Quiet areas close to lakes or community amenities provide easy access to outdoor activities and dining.
What are the best things to do in Winter Springs with kids?
Kids can enjoy local playgrounds, skate parks, or splash pads, and families often visit community events or nature trails. Public libraries and nature preserves around Winter Springs are also popular for family outings.
What are some of the best things to do in Winter Springs?
Explore community parks, attend local art or food festivals, and walk shaded nature trails around Winter Springs. The city has frequent cultural gatherings, outdoor fitness spaces, and welcoming local eateries.
How is the weather in Winter Springs?
Winter Springs has mild winters, averaging 49–72°F (10–22°C), and warm, humid summers, reaching 92°F (33°C). Rain is more common from late spring through summer, so lightweight layers and a rain jacket are often useful.
When is the best time to visit Winter Springs?
Many visitors prefer the months with milder temperatures and lower humidity, which are often found from late fall through early spring. Spring brings local blooms and a range of outdoor events.
What are the best places to visit in Winter Springs?
Winter Springs has inviting parks, nature preserves, and spaces for recreation. Central Winds Park is frequently suggested for outdoor activities, and local trails give opportunities to explore native landscapes.
What are some hiking trails in Winter Springs?
Winter Springs has greenways and multi-use trails ideal for walkers, joggers, and cyclists. Many local parks feature shaded paths and boardwalks through pine forests and wetlands.
What are some family activities we can do in Winter Springs?
Families often explore local parks, playgrounds, and nature trails around Winter Springs. Community centers may have sports courts, and seasonal festivals often feature kid-friendly activities and live entertainment.
What are some of the best day trip ideas from Winter Springs?
Many visitors explore state parks for hiking and wildlife viewing, or visit nearby springs for swimming and kayaking. Arts and science museums, botanical gardens, and cultural towns around the region are frequently suggested for day trips.
Are there any pet friendly accommodations available in Winter Springs?
Many accommodations in Winter Springs welcome pets, particularly in neighborhoods close to parks and outdoor recreation areas. These stays often provide convenient access to walking trails and pet-friendly spaces.
What are some local tips for visiting Winter Springs?
Check community calendars for cultural events or farmers markets during your stay. Early mornings and late afternoons are popular for outdoor activities, especially in the warmer months.
What is Winter Springs known for?
Winter Springs is known for its family-friendly atmosphere, green spaces, and community events. Locals and visitors often enjoy outdoor recreation and activities centered around parks and nature preserves.
What are the best hidden gems to explore in Winter Springs?
Many enjoy serene lakeside parks, scenic greenways, and small nature preserves tucked around Winter Springs. Locally owned shops and artist studios add unique character to less-traveled corners of the city.
What are the best foods to try in Winter Springs?
Winter Springs has a variety of American classics, Latin-inspired dishes, and Southern barbecue. Local cafes and bakeries are also known for fresh breakfast options and sweet treats.
What should I bring for a trip to Winter Springs?
Pack comfortable walking shoes, lightweight clothing for the warm climate, and a sun hat or sunglasses. A rain jacket is helpful in the wetter months, and sunscreen is recommended year-round.
What is the nightlife in Winter Springs like?
Nightlife in Winter Springs tends to be relaxed, with locally owned restaurants, bars, and casual pubs hosting live music on select evenings. Many gather at community events for food trucks and evening entertainment.
What are the most popular events or festivals in Winter Springs?
Winter Springs hosts recurring events such as an annual arts festival, holiday celebrations, and outdoor concerts. Seasonal gatherings often feature local vendors, performances, and family activities.
Are there family friendly vacation rentals in Winter Springs?
Many vacation rentals in Winter Springs are family friendly, featuring multiple bedrooms, outdoor play areas, and close proximity to parks or playgrounds. Listings often describe amenities like kitchens and laundry for added convenience.
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