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.

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Guest favorite
An outdoor seating area features blue Adirondack chairs and a patterned table, arranged on a concrete patio. Two large trees provide shade, and a swing is visible in the background. The space is accented with decorative rugs and greenery, fostering a relaxed atmosphere.
Home in Sanford
4.92 out of 5 average rating, 275 reviews

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.

Guest favorite
A screened wrap-around porch offers views of the lake, with sunlight casting striped shadows on the floor. Two lounge chairs are positioned for relaxation, while a colorful playpen is set against the railing. Decorative surfboards are mounted on the walls, enhancing the space's charm.
Cottage in Sanford
4.97 out of 5 average rating, 266 reviews

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.

Guest favorite
A spacious bedroom features two sets of twin bunk beds, accommodating multiple guests. A cozy seating area with a chair and ottoman is positioned in front of a mounted TV. Large windows invite natural light, enhancing the bright, modern decor.
Home in Casselberry
4.91 out of 5 average rating, 100 reviews

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

Top guest favorite
The pool area is enclosed with a protective screen, featuring a spacious heated pool surrounded by a wooden deck. A green umbrella provides shade over a small table and chairs, while a bright yellow building is visible in the background.
Home in Altamonte Springs
4.98 out of 5 average rating, 119 reviews

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

Guest favorite
Two sparkling glasses filled with a bright orange beverage are placed by the edge of a non-heated swimming pool. The pool area is surrounded by lush greenery and light stone walls, offering a serene outdoor retreat.
Guest suite in Oviedo
4.92 out of 5 average rating, 483 reviews

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

Top guest favorite
The exterior of the home features a welcoming front entrance with a gray door and arched window. The pathway is lined with colorful foliage, and tropical plants surround the entrance. A lamp post stands at the forefront, providing soft illumination amidst the lush greenery.
Home in Sanford
4.98 out of 5 average rating, 295 reviews

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.

Top guest favorite
A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.
Guesthouse in Longwood
4.98 out of 5 average rating, 142 reviews

"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.

Top guest favorite
A screened-in pool area features a clear blue pool surrounded by landscaped greenery. A stone waterfall adds a natural touch, complemented by decorative plants and a Zen-inspired statue. Sunlight filters through the trees, enhancing the tranquil ambiance.
Home in Longwood
4.97 out of 5 average rating, 133 reviews

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.

Top guest favorite
The image depicts a calm lake at sunset, with reflections of clouds and colors mirrored in the water. In the foreground, a fishing boat is anchored, positioned near the lake's serene shoreline surrounded by lush greenery.
Home in Longwood
4.95 out of 5 average rating, 175 reviews

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

Top guest favorite
The cottage exterior features a charming yellow facade with a metal roof, surrounded by lush greenery and a mix of plants. A patio area is visible, offering a shaded umbrella and seating amidst a peaceful outdoor setting, complemented by a small koi pond.
Home in Oviedo
4.96 out of 5 average rating, 312 reviews

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.

Guest favorite
Townhouse in Winter Springs
4.94 out of 5 average rating, 49 reviews

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!

Superhost
Home in Casselberry
4.83 out of 5 average rating, 64 reviews

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

When is the best time to visit Winter Springs?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$25,943 GYDG$25,943 GYDG$20,922 GYDG$22,177 GYDG$25,106 GYDG$25,106 GYDG$24,478 GYDG$25,106 GYDG$22,386 GYDG$25,315 GYDG$29,290 GYDG$27,407 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°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.