Vacation rentals with a patio in Winter Park

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Top-rated patio rentals in Winter Park

Guests agree: these patio rentals are highly rated for location, cleanliness, and more.

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Guest favorite
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.
Home in Altamonte Springs
4.94 out of 5 average rating, 100 reviews

Orlando Poolside Oasis

Welcome to the Orlando Poolside Oasis!! This property is located in a quiet suburb of Orlando, with easy access to both theme parks and the beaches. This 3 bedroom 2 bathroom pool home will allow you to vacation in comfort and style. We have recently completed many upgrades to the property, including a newly renovated kitchen and bathrooms. We hope you love this property as much as we do! The home is also very baby friendly (crib upon request, stroller, baby bath,etc)!We can’t wait to host you!😊

Top guest favorite
A heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.
Home in Lake Formosa
4.97 out of 5 average rating, 139 reviews

Spacious Home with Pool & Hot Tub near Downtown

Nestled in one of the most coveted neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5-min walk to tons of restaurants, bars, breweries, and boutique shops. Boasting a heated pool, hot tub, tiki bar, patio area w/seating & two living areas -you'll have ample room to play, entertain or relax in your Tropical Oasis! ☀ Harry P. Leu Gardens – 4 mins ☀ Orlando Museum of Art – 4 mins ☀ Universal Studios – 19 mins ☀ Walt Disney World – 24 mins ☀ The Mall at Millenia – 16 mins

Top guest favorite
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
4.98 out of 5 average rating, 166 reviews

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)

Top guest favorite
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
4.99 out of 5 average rating, 226 reviews

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.

Top guest favorite
A serene bedroom features a spacious bed dressed in crisp white linens, flanked by modern bedside lamps. A vibrant floral accent wall adds a pop of color, while light filters through plantation shutters, creating a calming atmosphere.
Home in College Park
4.96 out of 5 average rating, 100 reviews

Yale House in College Park 2 mi from Downtown

Yale House is a charming, historic 1927 home. This happy place is a stylish mix of nostalgia and modern life. The home is only steps away from shops & restaurants. The full kitchen and laundry have everything one needs for longer stays and includes a dedicated workspace with ethernet. There is wifi & 4 streaming TV’s with a huge comfy couch. Two bedroom choices provide for a peaceful rest. Driveway parking, outdoor spaces and a top of the line home gym make this unique for long term comfort.

Top guest favorite
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
4.98 out of 5 average rating, 131 reviews

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.

Top guest favorite
A serene pool area is surrounded by lush tropical greenery, including palm trees and bamboo. A spa is integrated into the pool with a stone wall feature. Chaises with striped cushions are positioned beside the water, and a spacious patio includes various stone pavers.
Guesthouse in Lake Cherokee
4.98 out of 5 average rating, 121 reviews

1924 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

Top guest favorite
A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.
Guesthouse in Longwood
4.98 out of 5 average rating, 124 reviews

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the quiet backyard and pool with your hosts. Half was between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from Interstate-4. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 29"-standard cabinets. We are not Handicap Certified but most wheelchair guests have not had issues. Grab bars are in the bathroom.

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
4.83 out of 5 average rating, 115 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

Top guest favorite
Tiny home in Baldwin Park
4.96 out of 5 average rating, 344 reviews

Lake View From Bed | Romantic Cabin

Romantic lakefront cabin with Costa Rica vibes in Orlando. Wake to sunrise views from your heated king bed. Sip Cuban espresso in the garden, walk or bike to Baldwin, Winter Park & Downtown or explore The Cady Way Trail. Enjoy a couple’s rain shower, grill, fire pit, and hammock. Guests love the peaceful setting, artful touches, and location minutes from the airport, arena & trails. Perfect for anniversaries, solo stays, and creative escapes. ⚠️Sorry - there is no lake DOCK access.

Guest favorite
A small, private room features a comfortable bed with a patterned blanket. A desk is positioned against the wall, accompanied by a chair. Natural light enters through a window, with decorative plants and simple wall décor enhancing the space.
Guest suite in Orlando
4.92 out of 5 average rating, 126 reviews

Adorable, private studio in College Park

Currently opening up this space for long term rentals (20-60 days). Perfect for travel nurses- about 10 min drive to Orlando Advent Health Hospital. This spot is perfect for 1 or 2 people looking for a private, welcoming place to stay! It is completely separate but does share a wall with the owners unit, so you could potentially hear some noises through there. The fenced in back yard is shared as well, both back doors open up to the yard. Its about 10 mins from downtown Orlando

Guest favorite
An outdoor seating area features comfortable couches adorned with colorful cushions. A coffee table sits in the center, surrounded by vibrant area rugs. Decorative lanterns hang overhead, and the backdrop includes lush greenery, creating an inviting space for relaxation and socializing.
Tiny home in Orlando
4.9 out of 5 average rating, 99 reviews

FunTropicalTinyGemUCF

Ready for an unforgettable getaway? Escape to our brand-new Tiny RV House — where fun meets relaxation in a one-of-a-kind space! Proudly a ‘GOLD Guest Favorite’ and ranked in the top 10% of all Orlando Airbnbs. 100% Unique. Features a very comfortable King Bed, WiFi, Smart TV, fireplace, central A/C, and heat. Enjoy stunning lake views front the screened room free of mosquitoes! Cozy, stylish, and packed with charm — come see why guests can’t stop raving!

Popular amenities for Winter Park patio rentals

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$25,124 GYDG$25,962 GYDG$26,799 GYDG$25,543 GYDG$24,077 GYDG$25,124 GYDG$24,496 GYDG$24,496 GYDG$23,030 GYDG$25,124 GYDG$25,962 GYDG$25,124 GYD
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Quick stats about vacation rentals with a patio in Winter Park

  • Total vacation rentals

    Explore 240 vacation rentals in Winter Park

  • Nightly prices starting at

    Winter Park vacation rentals start at G$4,187 GYD per night before taxes and fees

  • Verified guest reviews

    Over 12,600 verified reviews to help you choose

  • Family-friendly vacation rentals

    140 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 90 rentals that welcome pets

  • Vacation rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wi-Fi availability

    240 of Winter Park vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Park rentals

  • 4.9 Average rating

    Winter Park stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Winter Park's top spots, include Orlando Science Center, Harry P. Leu Gardens, and Orlando Museum of Art

Destinations to explore