
Vacation rentals with a pool in Winter Springs
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Winter Springs

Total vacation rentals
Explore 20 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 1,170 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winter Springs rentals

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

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

St. Augustine suite
Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

Villa with Guest House & Pool-Patio
Welcome to this Amazing House Pool-Patio with 4 Bedrooms + 2 Bathrooms and optional guest house to complete the 10 guests. True gem with covered summer kitchen, covered pergola, garage for two cars and a large driveway. 30 Minutes distance to Universal, Sea World, Volcano Bay and others. UCF in 15 minutes and Daytona beach/Cape Canaveral in 50’. Great restaurants and shops. The house is conveniently located for all attractions in Central Orlando. Airport is 25 minutes. SAFE NEIGHBORHOOD

"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

Bonheur Ala Maison
Bonheur A la Maison is the home that offers a beautiful, comfortable, spacious, convenient and all around happy feeling with the little extras and attention to detail to make you feel like you're basking in a lot of luxury for a simple price! Its everything you need from your blow dryer, to your plush robe and from your USB outlets at all bedsides to your built in wireless speakers for your music of choice. We tried to think of it all. Conveniently located near lots of shops and parks!

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.

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.

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!

Modern Tropical House Heated Salt Pool
☞Superhost 9 years ☞ Large Salt Pool (W/ heated option $ Sept-April) ☞3 Bedroom 3 Full Bath W/extra 4th queen daybed ☞ Easy access to the 417 East West express way (toll rd.) to get around Orlando ☞Easy smart lock self Check-in ☞ Driveway Parking ☞ Luxury bedding ☞Smart TV's with Netflix in each room ☞Dimmer mood lighting ☞Illuminated pool & landscape lighting ☞Full Kitchen ☞Dining & Picnic table seats 6 to 8 guests ☞Hi speed 231mb internet ☞Uber Eats Food Delivery
Popular amenities for Winter Springs rentals with a pool
House rentals with a pool

Recharge @ Timberland Lodge: Pool Hottub Sauna

Private Pool 4/2 Waterfront Oasis Weekly Discounts

Gated community XL pool Home 2500sq/f

2-bedroom home with pool near Kings Landings!

Markham Woods 4BR Pool Retreat near Attractions

Unique Spacious Home w/ Pool near Downtown Orlando

Orlando Poolside Oasis

Resort like 4/2.5 lake front saltwater pool
Condo rentals with a pool

Lovely Winter Park Home close to Hospitals !

VCR2-310 Deluxe Condo

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Cozy space 5/10 universal & epic

A luxurious living just 15 min/Disney

Waterfront Condo minutes to Disney & Universal

Modern Lake view Condo 1 mile from Disney

Chic Disney Resort Condo • Pool Access Near Parks
Other vacation rentals with a pool

Maitland-Orlando Area, FL. Pool House Bungalow

Sapphire Cottage - sleeps 6, on 5 acres with canal

Enjoy the Magic - Floating Cottage on the River

Farmhouse near the Springs

Spacious & lovely 3 bedroom Winter Park home

Cozy at Flamingo Cottage

The Lemon Cottage -NO EXTRA FEES

Luxury Villa: Heated Pool · Disney & Epic Universe
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 514 | ﺩ.ﺇ 444 | ﺩ.ﺇ 367 | ﺩ.ﺇ 551 | ﺩ.ﺇ 558 | ﺩ.ﺇ 606 | ﺩ.ﺇ 584 | ﺩ.ﺇ 378 | ﺩ.ﺇ 558 | ﺩ.ﺇ 514 | ﺩ.ﺇ 514 | ﺩ.ﺇ 514 |
| 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 |
Destinations to explore
- Miami Vacation rentals
- Four Corners Vacation rentals
- Orlando Vacation rentals
- Kissimmee Vacation rentals
- Miami Beach Vacation rentals
- Panama City Beach Vacation rentals
- Tampa Vacation rentals
- Fort Lauderdale Vacation rentals
- Savannah Vacation rentals
- Charleston Vacation rentals
- Hollywood Vacation rentals
- Jacksonville Vacation rentals
- Condo rentals Winter Springs
- Family-friendly rentals Winter Springs
- House rentals Winter Springs
- Rentals with a patio Winter Springs
- Rentals with outdoor seating Winter Springs
- Rentals with a washer and dryer Winter Springs
- Pet-friendly rentals Winter Springs
- Rentals with pools Seminole County
- Rentals with pools Florida
- Rentals with pools United States
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Daytona International Speedway
- Magic Kingdom Park
- Camping World Stadium
- Epcot
- Universal's Volcano Bay
- Kia Center
- Disney's Animal Kingdom Theme Park
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- University of Central Florida
- Old Town
- ESPN Wide World of Sports
- Disney's Hollywood Studios
- Playalinda Beach
- Aquatica
- ICON Park
- Tinker Field





