
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 G$4,184 GYD 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.

Lakefront,Sanford airport, Boombah, Venue 1902,UCF
The lake front cottage is located on a private estate 1 mile south of Sanford airport, 4 miles to Sanford historic district, and 3 miles from Boombha Sports Complex. This cottage has a Fully equipped kitchen, light bright liv/din area, screened wrap around porch. Perfect spot for your next family vacation or weekend get away. While staying at the cottage you are welcome to enjoy our paddle boards and kayaks. Also catch and release fishing. No pets. Discounts for non-refundable cancellations.

Oct. Specials, time to visit family. Long term ok
Remodeled, modern and spacious 3-bedroom home in the Orlando area. Perfect for a weekend trip to the parks or a family vacation! ✨Fully Remodeled ✨Modern Design ✨Fully Stocked Kitchen ✨Close to Wekiva Springs ✨Private Fire Pit Area ✨Short Drive to the Beach ✨Short Drive to Disney World and Universal Studios! ✨Close to Orlando Airport ✨Reliable High Speed Wifi ✨Smart TV's ✨Outdoor Grill ✨Patio ✨Easy Freeway Access ✨Quiet Neighborhood ✨Insurance Displacement Stays Welcome ✨Long Term Stays Welcome

Tropical Pool/Spa Home-Disney-Theme Parks-Beaches
Your Tropical Paradise is ready and fully furnished from top to bottom! The Pool area has a hot tub. Near all attractions. Top of the line furnishings. Split plan--Master Bedroom is a king suite, pvt bathroom, 2 seperate bdrms on the other side of house. Heated pool/ hot tub has an small add'l fee Moments from I-4 & 20-25 minutes to Disney, Sea World, Universal, Famous Names discount malls, 35 minutes to Daytona & New Symerna Beach. Cranes Roost Park, Altamonte Uptown/Mall, 5 min

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

Clean, cozy home in a GREAT location
This clean, comfortable home is in a peaceful neighborhood and centrally located to everything you may wish to enjoy while on your Central Florida vacation. Literally two to three minutes away from I-4, highway 417 and a multitude of shopping and dining options. Universal Studios, Sea World and Daytona International Speedway are all within about 40 minutes, while Disney World and Kennedy Space Center are about 50 - 60 minutes. Also easy access to Sanford and Orlando International Airports.

"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.

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

Cute cottage near UCF & trails. No cleaning fee
Our cottage is nestled behind Oviedo’s oldest home. The cottage boasts lots of windows with a beautiful view of the outdoors. Inside the cottage is a queen-size bed, table for 2-4, kitchenette with refrigerator, toaster and microwave, TV with Netflix and Prime, plus WiFi. There is a tall claw foot tub which can be difficult for people with mobility issues. The cottage is connected to the main house but has its own entrance and guests have complete privacy. There are no shared spaces.

The Springs -Townhouse in the Winter Springs
Charming 2-Bedroom, 1.5-Bath Townhouse. Your Perfect Home Away from Home. Whether you're here for business or leisure, this cozy retreat offers everything you need for a relaxing stay. Located just 15 minutes from Sanford Airport and 35 minutes from MCO Airport, it's also a short walk to a nearby park, making it ideal for those who love to explore. Plus, you're close to all the local attractions, so fun and adventure are just around the corner!

Entire Townhome | Stylish & Cozy | Peaceful
Bring the whole family and make this your home away from home. This townhome is equipped with everything needed to make your stay comfortable and feel at home. From washer and dryer, to a kitchen with everything needed to cook your meals. Parking is right in front of the townhome and the outdoor space can be used to relax and enjoy some quiet time. We are also roughly 30 minutes away from Universal and 40 from Disney for your park adventures!!
Popular amenities for Winter Springs vacation rentals
Other great vacation rentals in Winter Springs

Moxy Luxe Vacation /Heated Pool /Last-Minute Deals

Wana Chill Spot *Pool *Spa *Bar *Ping Pong *BBQ

Oviedo Escape- Heated Pool & Hot Tub

Pool House Paradise-Walk to Downtown Lake Mary

2BR Home in Heart of Longwood

The Perfect Escape • Orlando Access/Private Patio

Luxury Villa: Heated Pool · Disney & Epic Universe

Casa Alma Vacation Home Steps from LM Event Center
When is the best time to visit Winter Springs?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$25,943 GYD | G$25,943 GYD | G$20,922 GYD | G$22,177 GYD | G$25,106 GYD | G$25,106 GYD | G$24,478 GYD | G$25,106 GYD | G$22,386 GYD | G$25,315 GYD | G$29,290 GYD | G$27,407 GYD |
| 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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