Vacation rentals with outdoor seating in Winter Park

4.84 out of 5 average rating, 305 reviews

A charming tiny home features blue siding and is positioned near a tranquil lake. Lush greenery, including palm and shrubbery, offers a welcoming entryway. A smooth pathway leads to the entrance, with scenic water views in the background under a bright sky.

Tiny home in Orlando

The Blue Heron 6 Month Lakefront Tiny House Rental

The Blue Heron was the 8th tiny home to join our community in Orlando, Florida in 2018. You'll find this inviting accommodation steps from Lake Fairview and it can accommodate up to 4 guests. There is a queen-size bed in the lofted bedroom, in addition to a sofa bed in the living room area. A fully equipped kitchen and modern bathroom will keep you feeling at home, but you’ll likely want to spend the majority of your stay on the wide, wooden deck relaxing and enjoying the scenery. During your stay, take advantage of Florida lake life! We encourage all guests to take advantage our FREE kayaks and paddle board rentals as well as our yard games, hammocks, fire pit, propane grill, volleyball, cornhole and fishing gear upon request. Turn your tiny home experience into big fun on the lake! **This tiny house is not pet friendly**

4.99 out of 5 average rating, 133 reviews

A spacious living area features a large, deep-seated sectional couch adorned with decorative pillows. A wooden tray rests on the couch. A dining table with chairs is positioned near bright windows, enhancing the natural lighting in the room.

Home in Winter Park

Stylish newly updated home in Winter Park

Sleeps 8 people comfortably but can fit 10. This home has VERY CONVENIENT ACCESS TO I-4 making it easy to get to Orlando's most sought after attractions, including Park Avenue, Downtown Orlando, Rollins College, Leu Gardens, Mills Ave, Baldwin Park, College Park, Camping World Stadium, Amway Arena, SunRail, and many hospitals. SHORT WALK to 3 notable restaurants Also nearby: Universal Studios (20 min) Outlet Mall (20 min) International Drive (25 min) Orlando Airport (30 min) Disney (~30-40 min)

Apartment in College Park

A cozy bedroom showcases a queen bed with an orange floral duvet cover and matching pillows. Three pieces of wall art in soft hues are displayed above the headboard. A door leading to the private entrance is visible, providing easy access.

4.94 out of 5 average rating, 201 reviews

College Park/Winter Park separate 1 bed/bath 32804

255 sq ft duplex- w/ queen bed, workspace, kitchenette, large bathroom, private entrance & yard area. This gem is clean & quiet w/ complete blackout in bedroom. Bathroom has tons of natural light & 3 shower heads. There’s TV w/Roku, microwave, fridge & Keurig. Comfy, peaceful at I-4 Par exit # 44. No cleaning fee $20 pet fee. Universal 11 mi Kia Center 3 mi Airports (MCO) (SFB) 23 mi Orlando City Soccer 4.6 AdventHealth Orlando 0.6 mi Orlando Health, Arnold/Winnie Palmer 3.8 Rollins College 2 mi

Guest suite in College Park

A spacious bed with crisp white linens is positioned against a decorative panel that features wooden shutters. Modern bedside lamps provide soft lighting. In the background, a small kitchenette area is visible, equipped with a microwave and shelving.

4.95 out of 5 average rating, 154 reviews

Beachy Guest Suite in College Park

The beachy bungalow welcomes you to Florida. It's blue exterior will let you know you're in the right place. Your beachy suite is in the back of our home, it's old so the walls can be thin. This space has all you'll need for a weekend getaway including a mini fridge and microwave. It has the conveniences found in hotels with all the character of staying in a 1920s Floridian bungalow. There is a desk and chair for working remotely, a sofa for lounging, a king size bed, and a screen enclosed patio

4.88 out of 5 average rating, 561 reviews

A spacious pool house is visible behind a lush, green lawn, surrounded by trees. A paved path leads to the inviting pool area, while a gated fence provides added privacy. Sunlight filters through the leaves, creating dappled patterns on the grass.

Bungalow in Maitland

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 suite in College Park

A white door with a glass panel leads into the studio, framed by a decorative welcome mat on stone pavers. Lush green plants are positioned beside the door, adding a natural touch to the entrance. Soft shadows from nearby foliage create a calming atmosphere.

4.96 out of 5 average rating, 189 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

4.99 out of 5 average rating, 122 reviews

A well-equipped kitchen features white cabinetry and a granite countertop. A red vintage refrigerator adds a pop of color, while star-patterned tiles create visual interest. Two bar stools are positioned at the counter, and a rug runs along the floor, enhancing the space's warmth.

Guesthouse in Orlando

Baldwin Park Guest House

Welcome to Beautiful Baldwin Park, This Brand New Private sanctuary with modern day decorations, amenities and large screen television is the perfect place for a couple or single to experience the beautiful Orlando area. Conveniently located near the Orlando International Airport, Winter Park and downtown area Enjoy your morning coffee on the private patio . This entire property is very clean and well maintained, we look forward to being your host for your next central Florida visit

4.98 out of 5 average rating, 104 reviews

The exterior of the Cozy Cottage is designed with a welcoming green facade, featuring glass doors that open to a charming patio. A stone path leads to a small round table with chairs, complemented by a decorative fountain and lush greenery surrounding the area.

Bungalow in College Park

Cozy Cottage in College Park.

Whether you're coming to Orlando for adventure at one of the many theme parks, or a little R&R, the Cozy Cottage is the perfect place. It's charming, quiet and nestled in our back garden in College Park, located in The city of Orlando. Winter Park, Rollins college, lou gardens, Orlando Science Center, Advent Heath, Orlando health, Dr. Phillips center, Ivanhoe, lake eola, camping world stadium and the Kia center, are all in the immediate area. UCF, Full Sail and Florida Central too.

Tiny home in Baldwin Park

The spacious bed is adorned with a vibrant blanket, accentuated by plush decorative pillows in warm hues. A decorative table features a small vase of flowers, adding a touch of color to the rustic wooden interior, complemented by unique artwork on the walls.

4.96 out of 5 average rating, 289 reviews

Lake View from King Bed+Free Bikes+Kayaks+Espresso

The Perfect Couple’s Getaway❤️ (😊 read the reviews) - Espresso ☕️ - Couple’s Rain Shower -Beautiful View of Lake from Bed - Hammock in Garden - Propane Grill+Utensils - FREE Bikes+Kayaks+Paddle Boards - Smart TV + Streaming - Private Garden Yard with Seating Wake up to epic lake views from your king bed. Sip strong Cuban espresso, then launch a kayak or paddle board into calm waters—or bike into one of three charming nearby towns: Winter Park, Baldwin Park, or Downtown Orlando.

4.97 out of 5 average rating, 764 reviews

A warm indoor space features a spacious bed adorned with soft linens, complemented by wooden accents and greenery. A cozy sitting area is visible, along with a rustic desk and wall art that reads "TO THE MOON & BACK," creating a serene environment.

Tiny home in Spring Lake

The Little Treehouse 2 at Country Club of Orlando

With rustic urban charm, The Little Treehouse "2" is a perfect relaxation spot for your stay in the City Beautiful. This completely renovated 1926 carriage house downstairs unit is a 260 sq. ft. blend of cosmopolitan comfort and enchantment. Located 5 minutes from Downtown, Amway Arena, Camping World Stadium, 15 minutes to Universal Studios, 25 minutes to Disney and an hours drive to Florida's beautiful beaches! *Search "Little Tree House Orlando" in your browser for more info.

Guesthouse in College Park

A cozy seating area features a patterned armchair and a sleek gray sofa. A TV mounted on the wall displays a tranquil beach scene. Light streams in through a window with blinds, illuminating the natural wood floor and woven area rug.

4.93 out of 5 average rating, 245 reviews

Bungalow Near Epic Universe and Downtown Orlando!

Discover our charming cottage behind our bungalow in Downtown Orlando's College Park - conveniently located near Epic Universe and the Disney parks! Enjoy urban living with a small-town vibe, biking along tree-lined streets to restaurants, shops, breweries, and farmers markets. Private access, yard, and driveway and a beautiful park across the street! Conveniently access Winter Park (10 mins), Downtown Orlando (10 mins), I4 (2 mins), Disney and Universal (15-30 mins).

4.91 out of 5 average rating, 141 reviews

An aerial view of a rectangular swimming pool is surrounded by a stone patio. Lounge chairs are placed on either side of the pool, which is flanked by vibrant red bougainvillea flowers. A covered area with a sloped roof is visible in the foreground.

Apartment in Winter Park

Apt F -Modern Elegance in the Heart of Winter Park

Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two blocks to the Winter Park Village! Cozy and modern space. Pool, outdoor grill and bikes for your enjoyment. Enjoy the convenience and tranquility of one of Florida's greatest walking communities while residing in style and sophistication. The pool and grill stations are shared. Fast internet speed: 139MBPS download and 21.5 MBPS upload!

Vacation rentals for every style

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Popular amenities for Winter Park outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.92 out of 5 average rating, 204 reviews

A modern kitchen features white cabinets and stainless steel appliances, complemented by granite countertops. A large island with seating is positioned centrally, while the dining area is visible through glass doors leading to the backyard.

Home in Longwood

Cozy 3 Bedroom Home, Great location!!

LindaRating, 5 stars2 weeks ago

Had a great stay at Ahmads place, place was very spacious and clean and he supplied more than the usual one 1 roll of toilet paper, or 1 garbage bag and multiple towels and blankets and pillows. He really thinks ahead or goes by what he would want if he was renting. the outside is very deceiving, the inside is wonderful, airy, spacious l, and well decorated. our pup LOVED the fully fenced in yard and all of the space. the local squirrels kept her on her toes as the scampered amongst the trees. Across the street is a lovely little park, the has cranes, who also had their babies with them, it was very cute to watch them. Will look to rent again.

4.9 out of 5 average rating, 397 reviews

A cozy bedroom is depicted, featuring a spacious bed with white linens and a dark, quilted coverlet. Two modern teal lamps are positioned on white nightstands beside the bed. A landscape painting adorns the wall above, while soft natural light filters through sheer curtains.

Home in Orlando

Paradise suite( pets are not allowed)

GustavoRating, 5 stars2 weeks ago

Easy check in and check out. Had a good time!

4.99 out of 5 average rating, 135 reviews

A spacious private pool is enclosed by a screened structure, featuring a basketball hoop at one end. The crystal-clear water is surrounded by a concrete deck, while colorful flags decorate the fencing, adding a friendly vibe to the outdoor space.

Home in Orlando

Private pool home near Downtown

VanRating, 5 stars2 weeks ago

Great house. Great host. Always attentive and responsive. 2nd stay. Will go for a 3rd

4.86 out of 5 average rating, 123 reviews

A spacious living area features a modern sectional sofa arranged facing a stone fireplace. Large glass doors provide natural light and views of the outdoor space. Decorative plants and a wall-mounted mirror add elegance to the cozy atmosphere.

Home in Maitland

Bonheur Ala Maison

RyanRating, 5 stars1 week ago

Leah was a great host and very responsive. The house was great for me and my family while traveling for work. Awesome location in great neighborhood. I felt safe for my family while at work during the day. The pool area was great and the accommodations were suitable for our family. My 3 children had a blast and they had enough room to space out when necessary. Thanks Leah again for our stay and being a great host.

4.96 out of 5 average rating, 208 reviews

A cozy living area features a blue sofa accompanied by a light wood coffee table. A smart TV sits on a wooden entertainment unit. Two bar stools occupy a small kitchen counter in the background, which is visible through an open entryway. Light-colored walls are decorated with playful art.

Home in Thornton Park

Walk Everywhere! Lake Eola Thornton Park 1/1 Home

LaurenRating, 5 stars2 weeks ago

This place honestly has no flaws!! Great location!

4.93 out of 5 average rating, 182 reviews

The living area features a leather sofa and a stone fireplace as a focal point, complemented by a ceiling fan and natural light. A decorative mirror hangs on the wall above a console table, and the space connects to an updated kitchen visible through an open doorway.

Home in Orlando

The Orlando Retreat.

TaylirRating, 5 stars3 weeks ago

Had a wonderful time!! Pool was great and house was very comfortable! We always feel right at home this is our second stay!! 😁

4.92 out of 5 average rating, 53 reviews

A serene sunset paints the sky in hues of orange and pink, visible through the silhouettes of tall cypress trees. The calm waters of Lake Killarney reflect the vibrant colors, creating a peaceful ambiance along the landscaped lawn and tiled walkway.

Home in Winter Park

Lakefront Paradise Near Attractions

CathyRating, 5 stars1 month ago

What a lovely home this is. Very thoughtfully done and beautiful setting. Our contact person Gabriel was very very responsive. There were three couples staying here together and there was plenty of room to enjoy visiting or alone time.

4.89 out of 5 average rating, 147 reviews

The exterior of a two-story Spanish Mission-style home is depicted in soft twilight. The structure features arched entryways with large windows, surrounded by lush landscaping. A decorative lantern illuminates the front entrance, enhancing the inviting charm of the property.

Home in Delaney Park

3,000 Sqft Historic Home With Pool Near Everything

Alyssa MaeRating, 5 stars1 week ago

This was the perfect place to stay. This home is beautifully decorated, and such a nice little quiet retreat. I felt like I was staying in a home that was showcased in a magazine. The beds are so comfy and the pool is serene. I had the most relaxing weekend ever, thank you Nicole!

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Apartment rentals with outdoor seating

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.

4.99 out of 5 average rating, 153 reviews

Parent's Retreat!

TraceyRating, 5 stars2 weeks ago

The UCF Parents Retreat was absolutely perfect. It is just 10 minutes from campus! It’s a charming, cozy apartment that made us feel right at home. My daughter and I loved our stay, and even Lucy, our 12-year-old Cocker Spaniel, settled in immediately. The bed was especially comfortable, which was a huge plus. I would highly recommend this spot to anyone visiting UCF!

The kitchen features modern black appliances, including a refrigerator, microwave, and oven. Light-colored cabinets provide ample storage, while a granite countertop offers workspace. A sink with a faucet is positioned near a window, allowing natural light to brighten the area.

4.94 out of 5 average rating, 188 reviews

Lake Eola suite 2

Tony & GinaRating, 5 stars2 weeks ago

Alexander is an A+++ host. He cares and it shows that he takes pride in his rental. The place is super clean. super private and quiet. Just a stones throw from beautiful downtown too. 5 stars 👍

4.86 out of 5 average rating, 140 reviews

The image displays a bright and modern living space featuring a dining area with round table and blue chairs. The open kitchen is equipped with dark cabinets and appliances. A cozy living area is shown with a sofa, flat-screen TV, and natural light from a screened patio overlooking the pool.

Apartment in Kissimmee

1-104 Perfect location, Steps From The Heated Pool

LeslieRating, 5 stars3 weeks ago

Very responsive host, cozy place for us to enjoy our Florida trip.

A vibrant welcome sign for Orlando, Florida is depicted, featuring an artistic skyline with tall buildings. A colorful Ferris wheel is visible, along with various recreational activities by the water, including boats and beachgoers. Palm trees frame the scene, enhancing its lively atmosphere.

4.93 out of 5 average rating, 40 reviews

Luxury Apt + Pool + BBQ + Gym.

CheyenneRating, 5 stars3 weeks ago

This little studio was absolutely amazing for what I needed! It was a reasonable size and price. Also right down the street from the event I was going to! Lando is also an amazing host definitely would stay here again!

Apartment in Florida Center

A spacious studio is furnished with a large bed and a blue couch. Elegant decor is highlighted by a chandelier above, while a backdrop of a city skyline adorns one wall. Natural light filters through large windows, creating an open and bright atmosphere.

4.88 out of 5 average rating, 321 reviews

Carmen Romantic Studio W/Private Beautiful Terrace

MillyRating, 5 stars1 week ago

Liana’s place was amazing and the bed was so comfy. It was a nicely clean suite and was filled with supplies to help our stay feel comfortable and convenient. 17 mins away from disney springs and 8 mins away from Universal City Walk.

4.97 out of 5 average rating, 135 reviews

The living area features a modern sectional sofa adorned with decorative pillows. A sleek coffee table is positioned on a patterned rug, while large sliding doors lead to a balcony, enhancing natural light. An adjacent dining area with stylish chairs is visible in the background.

Apartment in Kissimmee

3121-402 Resort Lake View Disney Universal Orlando

GabbyRating, 5 stars1 week ago

We loved staying at Fonti’s place the host was quick to respond and very nice. The place was just how it was described and came with a beautiful view. We would love to stay here again if in Orlando.

4.91 out of 5 average rating, 108 reviews

A large resort-style pool, shaped like a Mickey Mouse head, is surrounded by palm trees and lounge chairs. Guests are seen relaxing on sun loungers and enjoying the water, with umbrellas providing shade in certain areas. Additional smaller pools are visible nearby.

Apartment in Kissimmee

Amazing Apartment in Orlando - Kissimmee

AmberRating, 5 stars2 weeks ago

I had a wonderful stay in Kissimmee, Florida! The place was exactly as described—clean, well-kept, and just like the photos. The location was perfect and made getting around easy. It truly added to the overall experience of the trip. I would definitely stay here again!

A charming gazebo with a red roof features six wooden swings surrounded by lush greenery. The two-story yellow building in the background has balconies and large windows, providing an inviting atmosphere. The area is well-lit and spacious, ideal for relaxation.

4.97 out of 5 average rating, 173 reviews

Peaceful Apartment on Small Urban Farm

JustineRating, 5 stars1 month ago

Everything was lovely! My husband, daughter, and I stayed for my son’s graduation from UCF. It was so convenient and close to campus. Also, it was a peaceful retreat as described. Highly recommend!

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Condo rentals with outdoor seating

4.87 out of 5 average rating, 103 reviews

A spacious outdoor area features several palm trees and seating arrangements with turquoise cushions. The backdrop includes a modern multi-story building. A barbecue area is visible, and lounge chairs are positioned around a sparkling pool, creating an inviting environment for relaxation.

Condo in Florida Center

Luxury Condo On I-Drive & One Mile from Universal

Jose EduardoRating, 5 stars1 week ago

We had an absolutely wonderful stay at Mike's place in Orlando! From the moment we booked, Mike was an exceptional host - incredibly communicative, friendly, and always quick to respond to any questions we had. We couldn't have asked for a better experience. We would highly recommend his place to anyone visiting Orlando and will definitely be back on our next trip!

4.92 out of 5 average rating, 101 reviews

An aerial view of the clubhouse area is displayed, featuring a large pool surrounded by lounge chairs. Palm trees provide greenery around the poolside, while guests can be seen enjoying the water. The architecture of the clubhouse complements the inviting outdoor space.

Condo in Orlando

Location,Location 3bd 2bth near parks conv.ct/Int.

LucindaRating, 5 stars1 week ago

Working with Isabela, was easy. The place was perfect for our needs. Beautiful, easy access to local attractions. Would highly recommend.

4.97 out of 5 average rating, 141 reviews

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

Downtown Condo w/ Treetop Views & Free EV Charging

LeoRating, 5 stars1 month ago

Marc’s place was truly a one of a kind! Really enjoyed my stay there and would definitely recommend to anyone to stay here. Place was perfect!

4.84 out of 5 average rating, 122 reviews

The spacious studio features a queen size bed with a dark quilt and white pillows, complemented by a sleek gray sofa bed nearby. A decorative wall with a leafy pattern enhances the ambiance, while large windows allow natural light to fill the space.

Condo in Florida Center

Studio close to Universal Studios + free Netflix

OscarRating, 5 stars3 weeks ago

Everything we could ask for and more at this sweet little spot near Universal Orlando!

4.85 out of 5 average rating, 487 reviews

A spacious terrace features comfortable lounge chairs with blue cushions and a stylish hanging chair. A small table accompanies two chairs, providing a perfect spot for relaxation. An umbrella offers shade, while the expansive view overlooks the surrounding area, enhancing the outdoor experience.

Condo in Florida Center

Modern Studio with Private Terrace near Universal

VernishaRating, 5 stars1 day ago

She was amazing! And sooo nice! We will definitely visit again!

4.82 out of 5 average rating, 108 reviews

A light-filled seating area features two plush chairs with decorative pillows, positioned near a large window dressed in soft curtains. A potted plant adds a touch of greenery, while a stylish rug lays on the hardwood floor, enhancing the overall cozy ambiance.

Condo in Orlando

2/2 PENTHOUSE DOWNTOWN with large Billiard room

HannahRating, 5 stars1 month ago

Frank let us check in 3 hours early, and was great with communication. The location was perfect for what we needed - and it was super clean. Would definitely stay here again!