Vacation rentals with a pool in Winter Park

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Winter Park

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 159 reviews

Comfortable Guest Suite-Stylish Altamonte Springs!

Enjoy a stylish guest experience at this centrally-located Altamonte Springs Florida guest suite. This luxury 830 sq ft unit offers a living room, kitchenette, bedroom, bathroom and large pool in the peaceful Spring Valley Farms residential community. It is located 8 miles north of downtown Orlando, a primo location close to downtown, both ocean coasts, Wakiwa Springs State Park, theme parks (Disney, Universal, SeaWorld, more), Crane's Roost, and many other great destinations in central Florida!

Guest favorite

Bungalow in Maitland

4.87 out of 5 average rating, 527 reviews

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.

Guest favorite

Home in Orlando

4.94 out of 5 average rating, 156 reviews

The Orlando Retreat.

When you visit the Orlando retreat, you will find every amenity that you, your family and fur babies will need to make this stay the best one yet! Unwind at its stunning pool and outdoor area equipped with a BBQ, lounging chairs, and outdoor dinning. In addition, this house features a beautiful fire place, home office, laundry room, and an updated kitchen with everything you will need. Finally, to top it off, free Wi-Fi and parking! * Within 30 min to Disney World, shopping centers, and MCO*

Guest favorite

Home in Orlando

4.9 out of 5 average rating, 126 reviews

Modern Tropical House Heated Salt Pool

Tropical House ☞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 ☞ Large Salt Pool (W/ heated option $ Oct-April) ☞ Driveway Parking ☞ Luxury bedding ☞65in Smart TV with Netflix in TV room ☞Dimmer mood lighting ☞Illuminated pool & landscape lighting ☞Pool Lounge Floats ☞Full Kitchen ☞Dining & Picnic table seats 6 to 8 guests ☞Hi speed 231mb internet ☞Uber Eats Food Delivery

Guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 330 reviews

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

Guest favorite

Guest suite in Oviedo

4.92 out of 5 average rating, 367 reviews

Oviedo Oasis:2/1 attached Guest Suite;Private Pool

Cozy 2 bedroom guest suite connected to host's primary residence but has its own entrance and guests have complete privacy. There are no shared spaces inside. Living room, 2 separate bedrooms and a full size bath. Amenities include a coffee bar, mini fridge , microwave, TV, Wifi and access to non-heated swimming pool. Listing does not include a full kitchen. Central to everything: UCF: 5 miles MCO Airport: 25 miles Sanford Airport: 11 miles Universal Theme Parks: 27 miles Disney: 40 miles

Guest favorite

Guest suite in Thornton Park

4.97 out of 5 average rating, 201 reviews

Orlando Oasis in the heart of Thornton Park

The perfect Oasis located in the beautiful Historic Thornton Park, one of the safest and quietest neighborhoods in Downtown Orlando, this brand new studio apt is perfect for couples, business travelers, and families of 3. Enjoy custom cozy decor, a super-comfy queen bed, full kitchen amenities, and a private view of the pool & downtown skyline. Easily walk to great parks, restaurants, bars, shopping, and Lake Eola. 20 min to Universal. 25 min to Disney. *VIDEO TOUR* available on YouTube.

Guest favorite

Home in Maitland

4.84 out of 5 average rating, 104 reviews

Bonheur Ala Maison - Boasts beauty comfort extras

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!

Guest favorite

Guesthouse in Orlando

4.87 out of 5 average rating, 258 reviews

Couples Oasis *Heated Pool* and Lake View

Have a romantic getaway in this SODO Couples Oasis Retreat with private pool or come work alone in this peaceful oasis. Perfect for couples or the busy profesional who want privacy and quiet with lake view while relaxing by the pool. Centrally located in SODO by downtown Orlando. Close to everything. Walk to great nearby eating places. Love ice cream Kelly’s Hand Made ice cream is a 5 minute walk from the house. *Heated Pool* available for $20 fee for first day and $10 every extra day.

Guest favorite

Farm stay in Oviedo

4.9 out of 5 average rating, 105 reviews

The Guest House in Oviedo countryside

If you love farm life, The Guest House is the place for you! We invite you to stay in the 600 sq ft apartment, one bedroom & one full bath. Our cozy country getaway is clean, fully furnished & situated on a 5-acre working equine therapy ranch. During your stay, you'll hear all the neighs, moos, bleats and clucks your heart desires! Come see a real farm in action from the comfort of a relaxing space, or while dining al fresco as you enjoy watching the horses go in and out of pasture.

Guest favorite

Home in Maitland

4.94 out of 5 average rating, 156 reviews

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

Superhost

Bungalow in Winter Park

4.87 out of 5 average rating, 117 reviews

Quaint Key West Pool Home

Welcome to Historic Winter Park Florida. Central Florida's gem Winter Park is filled with history, whimsy and magic as it is home to Rollins College, the Morse Museum with the world's most comprehensive collection of works by Louis Comfort Tiffany, delicious restaurants, Saturday Farmer's Market, unique stores along Park Avenue and the Scenic Boat Tour in operations since 1938. All bookings require minimum 30 day stay! Please message for pricing according to length of stay.