Vacation rentals with outdoor seating in Winter Park

4.98 out of 5 average rating, 168 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)

4.87 out of 5 average rating, 594 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.

4.98 out of 5 average rating, 231 reviews

A modern kitchenette features light cabinets and a combination of granite countertops. Stainless steel appliances, including a microwave and dishwasher, are visible. Pine wood floors run throughout, contributing to a warm appearance. Natural light fills the room through a window, illuminating the adjoining dining area.

Bungalow in Orlando

King/Queen Bungalow w/ porch | central vibey area

Our 1920's historic home is nestled in a quiet neighborhood just a few blocks from everything. The ColonialTown North district of Orlando (also called Mills/50) is a vibrant, central area with exceptional walkability to grocery stores, a trendy bar scene, LOTS of coffee and boba options, foodie restaurants and casual late night eats. When you're ready, retreat to our porch swing and watch the sunset reflect off the trees. We lived in this space for four years and left it just as we crafted it.

4.98 out of 5 average rating, 134 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 theme parks, or a little R&R, the Cozy Cottage is the perfect place. It's charming, quiet and nestled in our back garden with a stock tank pool in College Park, 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.

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.

4.93 out of 5 average rating, 281 reviews

College Park/Winter Pk 1 bed/bath private entrance

255 sq ft studio- queen bed, workspace, kitchenette, large bathroom, private yard area & entrance. 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. $20 pet fee No cleaning 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 1.9

Place to stay in Audubon Park

A modern structure with a sloped roof is set amidst lush greenery. The open patio features sleek outdoor seating, providing a comfortable space for relaxation. Large windows allow natural light to fill the interior, while the manicured lawn adds to the serene environment.

4.98 out of 5 average rating, 109 reviews

Hip RetroModern Lakefront Cabana w/ EV Charger

The Kiwi Cabana is a modern euro-style studio that offers the best in location, comfort, and ambiance! Relax with a glass of wine on the patio or dock & enjoy a gorgeous sunset on the lake. Light the fire pit and fire up the grill for a romantic evening. Luxe Queen Murphy Bed. Wifi. Cable. Outdoor Lighting & Sound System. Spacious Leather Sectional. Multiple Coffeemakers. Dishwasher. Microwave. CounterTop Oven. Electric Vehicle Charger at Dedicated Guest Parking Space. STR License #1009857

Superhost

A cozy bedroom features a comfortable queen bed with light blue bedding. Nightstands with lamps are positioned on either side. A wooden barn door and an artwork depicting foliage add a touch of warmth to the modern space, complemented by a sleek black floor.

Tiny home in Winter Park

4.84 out of 5 average rating, 116 reviews

Comfy Tiny Home @WP. Large Private Deck+Queen bed

This memorable place is anything but ordinary. Welcome to our charming TINY house in the heart of Orlando! Nestled in a quiet neighborhood, this cozy retreat offers the perfect blend of comfort, privacy, and convenience. Whether you're here for business or leisure, our centrally located TINY house is an ideal home base for exploring all that Orlando and Winter Park have to offer. ✅️Private Patio ✅️Free Parking ✅️Deck with outdoor seating 🎢10-15 min from Universal ✈️20-22 min to airport

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.

4.97 out of 5 average rating, 258 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.

4.97 out of 5 average rating, 815 reviews

A cozy space is illuminated by warm lighting and twinkling string lights. A comfortable bed with decorative pillows is framed by wooden accents. A small seating area features a television and has a view of the garden area with fire pit chairs, creating a relaxing outdoor ambiance.

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.

4.84 out of 5 average rating, 113 reviews

A modern kitchen is seen, featuring white cabinetry and a speckled granite countertop. Stainless steel appliances, including a microwave and toaster, are positioned conveniently. A small potted plant adds a touch of greenery, while natural light filters in through the window above the sink.

Condo in Winter Park

Lovely Winter Park Home close to Hospitals !

Lovely Condo close to Full Sail, Rollins College, Valencia College, UCF and Advent Health Winter Park Hospital. Close to Park Avenue - Winter Park’s shopping, dining and cultural gem – boasts more than 140 boutiques, sidewalk cafes, and museums, all in the shadow of oak-canopied Central Park. In addition to the shops, dining and cultural offerings, you can plan a trip around special events that include seasonal art shows, concerts and fashion events.

Tiny home in College Park

The exterior of a modern shipping container suite is displayed, featuring large windows that allow natural light to flood the interior. The surrounding landscape includes gravel and low-maintenance foliage, with a small deck leading to the entrance, emphasizing the blend of nature and contemporary design.

4.95 out of 5 average rating, 165 reviews

Luxury Container Home w/ {repaired} Hot Tub Oasis

Step into this unique experience: a shipping container transformed into a luxury 1 bedroom 1 bathroom suite. The space is perfect for couples, business travelers, tourists, and families. After a busy day in the parks or shopping, come back to a cozy outdoor paradise with lights strung up under a covered pergola. Lounge on the couch and enjoy a gas fireplace table, grill a meal on the Weber Spirit 2 gas grill, and soak your tired feet in the hot tub.

4.94 out of 5 average rating, 144 reviews

A bright bedroom features a spacious bed with a plush headboard and soft linens. Natural light enters through two windows, illuminating the room. A round mirror is mounted on the wall above a minimalistic desk with a chair, adding functionality to the cozy space.

Home in College Park

Priv. Modern Cozy CP 1B/1Ba Suite near DT Orl & WP

Private & Comfortable 1 bd/ba suite in a 2021 townhome with front view windows, queen size bed, walk-in shower& private entrance. Equipped w/ ceiling and portable fans, Roku smart TV, mini fridge/freezer, microwave, and Keurig. Located in a safe, quiet, walkable neighborhood. 5 minutes of College Park shops, 10 minutes from downtown Orlando, 25 minutes to Universal Studios, 30 minutes to Orlando International Airport, & 40 minutes to Disney.

Popular amenities for Winter Park outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

Home in Park Lake/Highland

A modern living area features a large sectional sofa in navy blue, accented by a round coffee table. A 65-inch Smart TV is mounted on the wall, while abstract art pieces adorn the adjacent wall. Natural light filters through sheer curtains, creating a comfortable ambiance.

4.97 out of 5 average rating, 159 reviews

Modern 3/2 in Ivanhoe Village

4.95 out of 5 average rating, 120 reviews

Home in Wadeview Park

Orlando Oasis! Free Laundry & Parking Near Disney

4.94 out of 5 average rating, 155 reviews

The cozy sleeping area features a spacious bed adorned with luxurious cotton sheets and coordinating pillows. A rattan headboard complements the tropical-themed wallpaper. A small seating area with a brown couch and decorative pillows is visible, adding to the inviting atmosphere.

Home in College Park

The Boho Jungalow - Private | HotTub | Downtown

4.91 out of 5 average rating, 166 reviews

A serene pool area is featured, reflecting the clear blue sky and surrounding greenery. The pool is bordered by a tiled edge, with colorful plant life adding vibrancy. A covered patio with a picnic table sits in the background, offering a shaded relaxation area.

Home in Orlando

Modern Tropical House Heated Salt Pool

4.91 out of 5 average rating, 187 reviews

Home in Orlando

Luxury Home by - SoDo + BEST local eats + Downtown

5 out of 5 average rating, 140 reviews

A spacious living area features light-colored wooden flooring and large windows allowing natural light to fill the space. Two comfortable sofas are arranged around a glass coffee table, and a potted plant adds a touch of greenery. A dining table is visible in the background.

Home in Orlando

Stay in the best neighborhood in downtown Orlando!

Home in Altamonte Springs

The inviting pool area is framed by a wooden deck, featuring two lounge chairs and a large umbrella for shade. The clear water reflects the blue sky and surrounding greenery, creating a serene atmosphere for relaxation.

4.94 out of 5 average rating, 101 reviews

Orlando Poolside Oasis

4.99 out of 5 average rating, 194 reviews

The exterior of a colonial-style home features inviting porches with several seating arrangements. The main entrance has a prominent door framed by windows, while symmetrical bay windows accentuate the facade. Lush greenery surrounds the property, enhancing the welcoming appearance.

Home in Lake Cherokee

Not just 2 private bedrooms; the entire upstairs!

Apartment rentals with outdoor seating

The studio features a spacious sleeping area with a large bed adorned with soft bedding. A colorful accent wall provides visual interest behind the bed. A television is mounted on the wall, while a modern dresser and a small dining table with chairs are also visible.

4.87 out of 5 average rating, 115 reviews

*NewRenovatedAPT*KINGbed*PetsOk+Priv Entry

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, 198 reviews

Parent's Retreat!

Apartment in Lake Eola Heights

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, 201 reviews

Lake Eola suite 2

A spacious living area is complemented by a modern kitchen featuring white cabinetry and stainless-steel appliances. A dark sectional sofa with decorative pillows faces the kitchen island, which is paired with two sleek bar stools. Large windows allows ample natural light.

4.93 out of 5 average rating, 123 reviews

DT Orlando 1/1 Sunset View - Free Parking

4.98 out of 5 average rating, 126 reviews

Private Rooftop Suite! No resort fees!

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.

4.89 out of 5 average rating, 352 reviews

Carmen Romantic Studio W/Private Beautiful Terrace

4.81 out of 5 average rating, 298 reviews

The bedroom features a spacious bed adorned with soft pillows and a textured throw blanket. Flanking nightstands hold stylish lamps, providing gentle lighting. A framed landscape image above the bed complements the neutral color scheme, and doorways to additional spaces are visible in the background.

Apartment in Clermont

Charming Lakefront Apt. Near Disney

Superhost

The studio features a cozy sleeping area with a patterned duvet covering a spacious bed. A large mirror hangs above the bed, reflecting natural light from nearby windows. Bedside tables with lamps and a white dresser add functional elements to the room.

4.86 out of 5 average rating, 471 reviews

Little Lulu's House

Condo rentals with outdoor seating

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.

4.88 out of 5 average rating, 127 reviews

Luxury Condo On I-Drive & One Mile from Universal

The living area features a sectional sofa and an accent chair, complemented by a coffee table and a console unit against a light-colored wall. Large windows allow natural light to fill the space, while decorative artwork adds a touch of color.

4.92 out of 5 average rating, 144 reviews

VCR2-310 Deluxe Condo

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.

4.92 out of 5 average rating, 132 reviews

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

A view of a serene lake is framed by lush greenery and palm trees. A wooden boardwalk leads toward the water, set against a backdrop of distant buildings under a bright blue sky with scattered clouds.

4.87 out of 5 average rating, 405 reviews

Lakefront Resort Studio -5 min to Universal

4.97 out of 5 average rating, 160 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 South Eola

Downtown Condo w/ Treetop Views & Free EV Charging

A cozy studio space is highlighted by a spacious bed adorned with a decorative blanket. A comfortable sofa and tufted stool provide additional seating. Light floods in through large windows, illuminating the soft tones of the wallpaper and area rug.

4.88 out of 5 average rating, 181 reviews

Luxury Studio, Near to Universal-Epic ,And Disney!

4.92 out of 5 average rating, 199 reviews

A modern living area features a plush blue sectional sofa complemented by two stylish lounge chairs. A light area rug sits under a chic coffee table, while large sliding glass doors provide a view of the outdoors and allow natural light to enhance the space.

Condo in Kissimmee

3171-206 Resort Lake View Disney Universal Orlando

A spacious living area features a large sectional sofa adorned with decorative pillows, positioned opposite a flat-screen TV on a modern console. Natural light enters through large windows, highlighting the open kitchen with wooden cabinetry and dining space. Decorative artwork adds a touch of color to the neutral walls.