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Vacation rentals with outdoor seating in Winter Park

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Winter Park outdoor seating rentals

House rentals with outdoor seating

Superhost
The outdoor pool area is surrounded by a screened enclosure, allowing for unobstructed views of the vibrant sunset. Palm trees are visible through the enclosure, and the pool water reflects the colorful sky in shades of blue and orange.
Home in Davenport
4.88 out of 5 average rating, 8 reviews

This home has it all, as well as top location.

PeterRating, 5 stars19 months ago
Had a great time at this rental. felt at home right away. Pool and outdoor kitchen was absolutely great. Location was great for everything we needed, grocery stores and local restaurants were really good. Only minor drawback was that the main TV did not work properly, and non of the room TVs were plugged up. did not impact us as we all stream to phones or tablets, but that could impact some families.
Superhost
An open kitchen featuring wooden cabinets and modern appliances is visible. A granite countertop with bar stools provides a space for casual dining. Decorative vases in blue hues sit on the counter, while a living area with comfortable seating is seen in the background.
Home in Davenport
4.75 out of 5 average rating, 65 reviews

Holiday home

Debra LynneRating, 5 stars3 months ago
Miguel helped us move in quickly after our home was destroyed by Hurricane Milton. He was very responsive to any question or issue.
Superhost
A spacious living area features a large leather sectional sofa facing a stone fireplace. Natural light floods the room through skylights and glass doors that lead to the screened-in pool. An adjacent dining area is visible, showcasing a wooden table with chairs.
Home in Altamonte Springs
4.81 out of 5 average rating, 124 reviews

Quiet Place, convenient to everything!

RustyRating, 5 stars2 months ago
James' listing was exactly what my family needed to gather together and celebrate Christmas. We all had our own separate living space and the openness of the kitchen and den area gave us plenty of room to gather together. The pool looked very inviting but the coolness of the season stopped us from plunging in. When we discovered a need for additional towels James was very quick to respond and had towels delivered in short order. Thanks James for a delightful stay.
Guest favorite
A bright and airy living area features modern furniture in neutral tones. A sleek gray couch rests beside a contemporary coffee table. A spacious kitchen island with seating is visible, along with stylish lighting fixtures hanging from the ceiling.
Home in Davenport
4.92 out of 5 average rating, 12 reviews

Modern Legends, Near Disney, kings bed ste

FranklinRating, 5 stars2 months ago
exceptional host. very informative. communication is top tier
Superhost
A covered outdoor seating area features four modern chairs arranged around a low table. A small refrigerator is positioned against a wall, with sliding glass doors leading to the interior. Natural light enters the space, highlighting the simple, functional design.
Home in Orlando
4.85 out of 5 average rating, 212 reviews

King suite , Modern house perfect for vacation

JaromeRating, 5 stars2 weeks ago
Jose was an incredibly accommodating and thoughtful host. From the moment I booked, he made sure everything was seamless and stress-free. His communication was prompt and helpful, and he went out of his way to ensure I felt comfortable during my stay. The space was clean, well-maintained, and had all the amenities I needed. Jose's attention to detail and warm hospitality truly made it feel like a home away from home. If you're looking for a reliable and welcoming Airbnb host, I can’t recommend Jose highly enough. I would happily stay here again!
Superhost
Home in Kissimmee
4.78 out of 5 average rating, 9 reviews

Amazing townhouse in Champions Gate

EllenRating, 5 stars4 months ago
We loved the place and highly recommend staying there. Even though our stay started when the hurricane hit, Gabriel & Gabrielle made accommodations. Hope to go again one day.
Guest favorite
A single-story home is presented with a light gray exterior and a welcoming front entrance. Flanking palm trees and manicured landscaping add color to the yard. A smooth driveway leads to a two-car garage, emphasizing the spaciousness of the property.
Home in Orlando
4.93 out of 5 average rating, 30 reviews

Relaxing four bedroom getaway built 4 long stays

DaleRating, 5 stars1 week ago
Edwin was a great host and took the time to ensure that our check in was a success. We would certainly stay here again if we were in the area. 5⭐️
Guest favorite
Home in Orlando
4.92 out of 5 average rating, 25 reviews

Modern Lakehouse Retreat

DavisRating, 5 stars2 weeks ago
This place is awesome. A very beautiful and modern house with all kinds of great amenities. The location is unbelievable on beautiful Lake Barton and right next to the Orlando Executive Airport. I highly suggest this Air BNB to anyone that likes a nice clean house close to downtown Orlando. Neighbors on both sides are very friendly! Awesome place 10/10 😎

Apartment rentals with outdoor seating

Superhost
The living area features a spacious gray sofa with decorative pillows and a coffee table, complemented by a large flat-screen TV on the wall. A dining area is visible in the background, and a kitchen is neatly equipped with modern appliances. The bedroom showcases a king-sized bed with layered bedding and a ceiling fan overhead.
Apartment in Kissimmee
4.84 out of 5 average rating, 105 reviews

1-105 Pool Side, Minutes from Disney, gated Resort

AmandaRating, 5 stars1 week ago
Anthony has a wonder place. Just what I needed for my stay for the two of us. Close to every place i needed and lots of food choices as well. Anthony was quick to reapond to my questions and needs. Will definitely book again in future.
Guest favorite
A spacious private terrace features multiple blue loungers and a dining table with wooden chairs. A shaded canopy bed invites relaxation, while the surrounding area showcases views of the skyline under a partly cloudy sky.
Apartment in Florida Center
4.92 out of 5 average rating, 39 reviews

Penthouse With EPIC Views

EmilyRating, 5 stars1 week ago
I decided last minute to book this penthouse to spend one last night in Florida for my birthday. My stomach dropped when I walked in. It was BEAUTIFUL. The views, the decor, the bed was the most comfortable I’ve ever slept on! Toby’s instructions were so clear I never had to contact him once my whole stay. I felt at home and like I could relax and enjoy. There was so much privacy. I could go on and on. I will for sure be back with my sisters, it’s way to amazing to experience to not share 😍
Guest favorite
The living area features a spacious sectional sofa with rich teal upholstery and colorful accent pillows. Vibrant artworks adorn the walls, while decorative string lights create a warm atmosphere. A unique white sculptural chair and a low coffee table complete the eclectic and inviting space.
Apartment in Thornton Park
4.98 out of 5 average rating, 41 reviews

Vibrance & Views on Main | Free Prkg | Balcony

AudrieRating, 5 stars6 days ago
Cute apartment with a lovely balcony! Everything was clean and communication was great 👍
Guest favorite
A cozy living area features a dark gray sofa and armchair, complemented by a light rug on the floor. A small desk with a chair sits against the wall, and a wall-mounted television is positioned above. Natural light pours in through the front door with a window.
Apartment in Orlando
5 out of 5 average rating, 133 reviews

Parent's Retreat!

KathrynRating, 5 stars4 days ago
Beautiful place in a nice neighborhood. Good location in relation to Kennedy Space Center and UCF campus. Good assortment or food around! Worked well with our two dogs. Bathroom floor tile is slippery, but mats are provided -just be cautious!
Guest favorite
A contemporary living area features a navy blue sofa with yellow accent pillows, positioned next to a round coffee table. A colorful area rug with floral patterns enhances the floor. A potted plant adds a touch of greenery to the space, contributing to a stylish ambiance.
Apartment in Davenport
5 out of 5 average rating, 10 reviews

Stunning Luxury Retreat near Disney!

DesireeRating, 5 stars7 months ago
I would definitely stay again while visiting Orlando. Close enough to attractions and far enough to maintain peace. Neighborhood was very beautiful. Pool and gym were both beautiful with sufficient equipment. Apartment was nice and clean as pictured. Thanks Ari!!!
Guest favorite
Apartment in Orlando
4.91 out of 5 average rating, 82 reviews

DT Orlando High-Rise Sunset View - Free Parking!

KandiceRating, 5 stars1 week ago
Glorious was a great host ! The unit was very clean and in a great location. She was very responsive. We stayed an extra night last minute and she was very flexible and made the experience pleasant. Absolutely can’t wait to book again !
Guest favorite
Apartment in Winter Garden
5 out of 5 average rating, 15 reviews

15 Min to Parks,Pet-Friendly, King Bed & Amenities

AlyseRating, 5 stars3 weeks ago
We stayed here for 8 days for our honeymoon and it was great! The place was very close to all of the things we chose to do. It was a good space for 2 people and cozy. I would definitely recommend staying here if you plan on going to any Disney parks or for a special occasion.
Guest favorite
Apartment in Orlando
4.96 out of 5 average rating, 26 reviews

Modern downtown apartment

JordanRating, 5 stars1 day ago
Great place with lots of space. Host even let me check in 2 hours early. Super clean and very well appointed. The only improvement I could suggest would be replacing the TV in the bedroom with one that actually works.

Condo rentals with outdoor seating

Guest favorite
A large outdoor pool area features clear blue water and a series of palm trees lining the edges. A water slide is visible on the left, and sun loungers are placed nearby. A spacious patio area is located in the background, providing shaded seating.
Condo in Four Corners
4.87 out of 5 average rating, 141 reviews

LUXURY RESORT & GOLF CONDO MIN CLOSE TO DISNEY

MitchellRating, 5 stars1 week ago
The place was perfectly located and had a great resort amenities. Not far from Disney and the golf course was fantastic. Would 100 working with Ahava as she does everything she can to ensure a great stay.
Guest favorite
A spacious living area features a comfortable sofa and two turquoise chairs, inviting relaxation. A large rug with geometric patterns anchors the space, while a modern art piece adds a colorful focal point. Natural light floods in through large windows, highlighting the open layout.
Condo in Orlando
4.97 out of 5 average rating, 135 reviews

Downtown Condo w/ Treetop Views & Free EV Charging

RhondaRating, 5 stars1 week ago
Great place to stay! Very clean and well maintained in a quiet location yet close to everything in downtown. Comfortable bed and sheets was a plus! Clear instructions and felt very safe. Marc and Jacob were great communicators! It was a pleasure staying here!
Guest favorite
Condo in Kissimmee
4.97 out of 5 average rating, 123 reviews

Disney Oasis

TabithaRating, 5 stars1 week ago
We had an excellent stay at Disney Oasis! Two adults and three kids (8, 6, and 2) and the child friendly amenities, provided toys, and bunk beds were perfect. Pool toys and towels were provided which made packing much easier. The Disney décor was adorable. The balcony was a great spot to sit and unwind. We LOVED the pool, waterslides, and game room. The marketplace right next to the pool has a great selection of hot food, drinks, and treats making our "rest day" at the pool super easy and low-key. 10/10 fun pool atmosphere, all staff was very friendly. We were super close to all the Disney parks, and with the pool and great amenities we loved staying "off-property". The bed space, full kitchen, and in-room laundry was 100% worth being out of the "bubble". Giovanni & Amy messaged us welcome materials pre-stay, checked in with us on our first day, mid-stay, and last day and were super responsive to anything we needed. We will definitely stay here again next time we're in Orlando!
Superhost
Condo in Orlando
4.81 out of 5 average rating, 128 reviews

Resort Condo: 2BR w/ Balcony near Disney

JoanRating, 5 stars7 months ago
We had a great stay in Vista Cay. We loved being close to the pool. It was very quiet at night and our condo was as expected. There were a few very worn areas on the couch and rug. The beds were comfortable and we had ample space. We would definitely stay again.
Superhost
A modern kitchen features dark cabinetry paired with a granite countertop. Stainless steel appliances, including a microwave and oven, are prominently displayed. A decorative sign reading 'Home' is mounted on the wall, adding a touch of warmth. Kitchen utensils are organized neatly beside the sink.
Condo in Kissimmee
4.82 out of 5 average rating, 122 reviews

Lovely 3BR 2BA condo, great amenities and location

BeverleyRating, 5 stars2 weeks ago
We lived this cute little apartment. Clean close to most activities, a short 15-20 minute drive to the parks and the dance competition. One and only one issue. The gate entrance was difficult. Understandable for security reasons but time consuming and difficult. Other parents/friends stayed in the same apartment complex. Their owner provided a gate pass. Hopefully their future guests will receive one too.
Guest favorite
An aerial view of a community pool area features a curvilinear swimming pool surrounded by lounge chairs and shaded seating areas. A hot tub is located adjacent to the pool, surrounded by lush landscaping and palm trees. The clubhouse is visible, contributing to the inviting atmosphere.
Condo in Kissimmee
4.89 out of 5 average rating, 207 reviews

Marvelous apartment near Disney first floor

SantiagoRating, 5 stars1 week ago
Thank you Anderson for everything, your response, support, etc. Even, your additional help after I left the apartment 🙏
Guest favorite
A winding lazy river pool is surrounded by lush palm trees and tropical landscaping. Water features, including slides and spraying elements, create an engaging atmosphere. Steps lead into the pool, which is framed by natural stone and tile, offering a serene escape in a vibrant setting.
Condo in Kissimmee
4.98 out of 5 average rating, 122 reviews

Condo on the top floor with lake view near Disney!

StephanieRating, 5 stars6 days ago
Spacious, clean with everything you needed to stay with a family. Felt right at home. Would highly recommend this stay! Thank you!
Guest favorite
Condo in Orlando
4.92 out of 5 average rating, 125 reviews

LARGE Lake View Condo 2 KINGS 2 BATHS near DISNEY

KellyRating, 5 stars4 months ago
Absolutely a wonderful place to stay. Very comfortable and spacious. We loved the view from the balcony & main bedroom, as we watched the breathtaking sunrise over the lake every morning. At night we could step out on the back side (shared space) of condo to watch Disney & Epcot Fireworks in the distance. The pool, hot tub, and tiki bar was a great place to relax after a day at the "Parks". My daughter loved the wooden pier & walking path. The amenities, all the extras, are above & beyond what was mentioned in listing. We decided to go with an A B&B because we were traveling with my elderly mother, sister & daughter & we were seeking additional space & we got exactly that. We could not have been more pleased. The drive to the Disney Parks was easy from this location. We loved that we were walking distance (thru the parking lot) to 2 Disney Stores, subway, miniature Golf & a dollar store. Chick Filet is across the street. We couldn't have been more pleased.

Quick stats about vacation rentals with outdoor seating in Winter Park

  • Total rentals

    160 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    10K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    40 properties have a pool

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