Holiday rentals in Winter Springs

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Winter Springs

  • Total holiday rentals

    Explore 90 holiday rentals in Winter Springs

  • Nightly prices starting at

    Winter Springs holiday rentals start at €17 per night before taxes and fees

  • Verified guest reviews

    Over 4,050 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    90 of Winter Springs holiday rentals include wifi 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 holiday rentals in Winter Springs

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

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Superhost
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, 270 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 favourite
A well-lit bedroom features a spacious bed dressed in a light blue coverlet. A nightstand with a lamp is located beside the bed. An closet with sliding doors is visible, providing additional storage. Neutral-toned walls and tiled flooring contribute to a serene ambiance.
Guest suite in Casselberry
4.85 out of 5 average rating, 100 reviews

Comfortable and quiet place

Forget your worries in this spacious and serene space, we offer our guests k cups coffee(Victor Allens), sweteners (splenda) and "Oasis Bliss" personal care amenities( shampoo,conditioner, body lotion, bar soap).Private kitchen and bathroom. Also located less than an hour to Disney and Universal parks. Many restaurants and shoping centers around the area, 15 miles- 20 mins to "Orlando Sandford International Airport". Feel free to ask questions and our family will be in contact with you, thanks

Top guest favourite
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, 477 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

Superhost
Treehouse in Geneva
4.89 out of 5 average rating, 1,148 reviews

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.

Top guest favourite
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.
Guest house in Longwood
4.98 out of 5 average rating, 140 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 favourite
A charming lakefront cottage is viewed from across the water, showcasing its blue exterior. The porch area includes a deck with seating, and two light-colored lounge chairs are positioned on the grassy lawn, surrounded by lush greenery and trees.
Cottage in Altamonte Springs
4.99 out of 5 average rating, 153 reviews

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.

Top guest favourite
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, 128 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 favourite
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, 172 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 favourite
A bright outdoor lounge area is furnished with comfortable wicker sofas, set against a backdrop of large windows overlooking a shared saltwater pool. A colorful area rug adds vibrancy, while a ceiling fan circulates air within the space.
Guest suite in Lake Mary
4.96 out of 5 average rating, 389 reviews

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.

Top guest favourite
The screened-in pool area features a tranquil pool with a soft blue hue, surrounded by white decking. A small table holds a lit lantern beside two lounge chairs, providing a serene space for relaxation under the evening sky.
Home in Maitland
4.98 out of 5 average rating, 128 reviews

Florida Poolside Paradise a Great Place to Unwind!

Welcome to our exquisite 4-bedroom vacation rental in the heart of Maitland, Florida – a true gem where luxury meets convenience. This upscale home boasts fine furnishings and a private pool, making it the ideal retreat for families or groups seeking both comfort and style during their Sunshine State getaway. The house is located in a residential neighborhood with plenty of restaurants and shopping within a 5 minute drive. Convenient location off Rt 436. and half hour to the airport.

Top guest favourite
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, 311 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.

Top guest favourite
A spacious bedroom features a large bed dressed in neutral tones, accented by decorative pillows. Natural light filters through angular windows, illuminating the space. A seating area with a gray bench is positioned at the foot of the bed, and wooden walls provide a warm backdrop.
Home in Longwood
4.99 out of 5 average rating, 134 reviews

Private 4-Bedroom home with pool!

Entire home located on 1 acre of land in the luxury neighbor hood of Markham Woods. This property is the ideal place to stay for a family vacation, or business trip. Take a swim in our large pool and enjoy the Florida Sun! Please add exact number of your guests, in your booking! Please NO Parties or gatherings! (Family visits are welcome 🤗) Please NO smoking on the property. If any violation occurs, your stay will be terminated immediately, and you will be charged a $1,500 fine!

Popular amenities for Winter Springs holiday rentals

When is the best time to visit Winter Springs?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price€108€108€87€114€113€111€102€105€93€106€122€114
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.