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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 141 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!

Sep. 20 – 27

$191 CAD per night

Guest favourite

Apartment in Orlando

4.93 out of 5 average rating, 101 reviews

Apartment, 7 Min to Orlando Airport/ Lake Nona

Complete private unit . A Private Door inside the room to step out to the pool .1 Bed/1 Bath, 2 TV’s , Netflix Amazon, sitting area, and and a small kitchen, We a Manual Slingshot available for rent, the rent for the Slignshot will be $200 per day. Pool area will be available all the time .We just build a door inside the room that way is easy access. This place is 25 Minutes driving to Disney World and most Parks, Lake Nona is 10 minutes away. We are Close to UCF, lake Nona, MCO, Waterford lakes

Oct. 28 – Nov. 4

$189 CAD per night

Guest favourite

Guest suite in Orlando

4.99 out of 5 average rating, 124 reviews

Beautiful studio with pool & close to attractions!

An amazing studio space, attached to the main home, with private entrance, King size bed, full bath, and kitchenette. Recently renovated and very comfortable. New Mitsubishi mini-split AC system and a Nespresso Machine for your morning coffee. Access to pool area, gazebo, and washer/dryer outside! Centrally located: under 20 minutes to the airport, 5 minutes to Florida Mall, 10 minutes to Mall at Millenia, under 20 minutes to Universal Studios, 35 minutes to Disney, and 10 minutes to Downtown!

Oct. 13 – 20

$145 CAD per night

Guest favourite

Bungalow in Maitland

4.86 out of 5 average rating, 490 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.

Jul. 14 – 21

$164 CAD per night

Guest favourite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 315 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

Jan. 4 – 11

$150 CAD per night

Guest favourite

Guest suite in Oviedo

4.91 out of 5 average rating, 313 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

Feb. 16 – 23

$171 CAD per night

Guest favourite

Guest suite in Orlando

4.97 out of 5 average rating, 184 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.

Aug. 27 – Sep. 3

$222 CAD per night

Guest favourite

Guesthouse in Orlando

4.88 out of 5 average rating, 218 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.

Sep. 13 – 20

$202 CAD per night

Guest favourite

Guest suite in Orlando

5.0 out of 5 average rating, 430 reviews

LAKEFRONT STUDIO APARTMENT (private entrance)

This studio apartment is located in the lower level of our home and is perfect for one or two people. It has a private entrance, a king bed, overlooks the pool and the lake with views of downtown Orlando. Please note there is no kitchen, but there is a wetbar with microwave and mini fridge. In addition to the indoor shower, there is also a outdoor shower and a dock with canoe. Please also note the inside ceiling height is lower than average at 6'3”.

Jan. 6 – 13

$339 CAD per night

Superhost

Apartment in Maitland

4.81 out of 5 average rating, 262 reviews

At Mine | Elegant Double Suite in North Orlando

Experience ultimate comfort at our Maitland, FL hotel, ideally located just north of Downtown Orlando. we're the area's largest hotel. Enjoy the convenience and luxury of plush bedding, modern furnishings, and upscale Grohe showers in your room. Relax by our outdoor pool, keep fit in the 24-hour gym, and access the Genesis Health Club. With over 15,000 square feet of event space, secure parking, and free Wi-Fi, we've got you covered.

May 3 – 10

$100 CAD per night

Guest favourite

Guesthouse in Orlando

4.98 out of 5 average rating, 350 reviews

Lakefront Seclusion modern guesthouse+Pool+Hot tub

An oasis in the city is what you will be surprised to find here at your guest house, located on a peaceful estate on the shore of Lake Hourglass. Secluded from the noises of the city, but still just minutes from everything, it's the perfect base to explore Orlando from, or perhaps to enjoy a staycation at if you're a local! For check out, please just enjoy your stay with us, you don’t need do any tidy or clean steps for us.

Sep. 17 – 24

$338 CAD per night

Guest favourite

Guesthouse in Orlando

4.99 out of 5 average rating, 197 reviews

Livingston Pool House- In The Heart of Downtown

Welcome to the Pool House! Our newly renovated detached pool house is located in the heart of downtown Orlando, in the Lake Eola Heights Historic District. We are two blocks to beautiful Lake Eola and all the dining and entertainment that Orlando has to offer. The Pool House has everything you need for a relaxing time at home, yet all the entertainment at your finger tips! Downtown living with a tropical escape!

Dec. 14 – 21

$370 CAD per night