Airbnb Properties for Sale in Winter Garden, FL

Looking for a vacation rental investment in Winter Garden, FL with high ROI ?

Explore a range of newly added short-term rental homes in Winter Garden, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Winter Garden, FL

Q: What is the average Airbnb occupancy rate in Winter-garden, FL?

In May 2026, the average Airbnb occupancy rate in Winter-garden is 78%.

Q: How to get Winter-garden, FL Airbnb data?

Airbnb data on vacation rentals in Winter-garden, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter-garden, FL market insights, guest information and booking details, seasonality trends and historical Winter-garden, FL Airbnb performance data .

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
13836 Daniels Landing Cir Winter Garden, FL HOT PROPERTY! Only Townhome available for sale in BEAUTIFUL and desirable Daniels Landing...	2 beds \| 2 baths \| 1,234 sq.ft.	$300,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 2.63% Airbnb Rental Income: $2340 Traditional Rental Income: $1660 Airbnb ROI: 2.98% Traditional ROI: 2.63%
264 BLUE STONE CIRCLE Winter Garden, FL LOCATION, LOCATION, LOCATION! Welcome to 264 Blue Stone Cir in the highly desirable Winter...	4 beds \| 3 baths \| 2,538 sq.ft.	$725,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 3.53% Airbnb Rental Income: $5064 Traditional Rental Income: $3698 Airbnb ROI: 4.02% Traditional ROI: 3.53%
15558 Sandfield Loop Winter Garden, FL NEW PRICE MAKES THIS THE BEST DEAL ON THE BLOCK! This one will check ALL your boxes...Tayl...	4 beds \| 3 baths \| 4,307 sq.ft.	$765,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.23% Airbnb Rental Income: $5064 Traditional Rental Income: $3134 Airbnb ROI: 3.49% Traditional ROI: 2.23%
14844 Driftwater Dr Winter Garden, FL Come see this gorgeous 2016 Lennar built, 4 bedroom 2.5 bathroom, 2,000 sq ft townhome in ...	4 beds \| 2 baths \| 1,990 sq.ft.	$429,990	Airbnb cash on cash: 6.69% Traditional cash on cash: 2.53% Airbnb Rental Income: $5064 Traditional Rental Income: $2356 Airbnb ROI: 6.69% Traditional ROI: 2.53%
897 Landrum Dr Winter Garden, FL Welcome to one of Winter Garden's most coveted addresses â nestled in the heart of the G...	4 beds \| 3 baths \| 3,012 sq.ft.	$899,900	Airbnb cash on cash: 2.73% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3383 Airbnb ROI: 2.73% Traditional ROI: 1.96%
9338 Tyrella Pine Trl Winter Garden, FL You will love this beautiful 4 bedrooms, 2.5 bathrooms, 2 car garage home located in the d...	4 beds \| 2 baths \| 1,696 sq.ft.	$449,000	Airbnb cash on cash: 7.75% Traditional cash on cash: 4.89% Airbnb Rental Income: $5064 Traditional Rental Income: $2829 Airbnb ROI: 7.75% Traditional ROI: 4.89%
7832 Freestyle Ln Winter Garden, FL BETTER THAN NEW and less than 1 year old. Ideal MODERN one story floor plan with all the r...	4 beds \| 3 baths \| 2,650 sq.ft.	$1,075,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 1.44% Airbnb Rental Income: $5064 Traditional Rental Income: $3030 Airbnb ROI: 2.44% Traditional ROI: 1.44%
261 Zachary Wade St Winter Garden, FL *** Multiple offers received, deadline for highest and best is Wednesday 06/01/2022 @ 10am...	4 beds \| 3 baths \| 3,728 sq.ft.	$1,699,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 0.65% Airbnb Rental Income: $5064 Traditional Rental Income: $3554 Airbnb ROI: 0.96% Traditional ROI: 0.65%
10007 Little Alcove Loop Winter Garden, FL Don't wait to build new- enjoy the upgraded finishes in this Emerald Home now! Beautifully...	4 beds \| 3 baths \| 2,921 sq.ft.	$999,990	Airbnb cash on cash: 2.84% Traditional cash on cash: 2.49% Airbnb Rental Income: $5064 Traditional Rental Income: $3702 Airbnb ROI: 2.84% Traditional ROI: 2.49%
7266 Desert Mandarin St Winter Garden, FL Great investment opportunity! Welcome to this beautifully maintained home built in 2018, f...	4 beds \| 3 baths \| 2,365 sq.ft.	$595,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 2.29% Airbnb Rental Income: $5064 Traditional Rental Income: $2890 Airbnb ROI: 4.34% Traditional ROI: 2.29%
15508 PEBBLE RIDGE STREET Winter Garden, FL This is the one youâve been waiting for. A beautifully maintained four bedroom pool home...	4 beds \| 3 baths \| 2,763 sq.ft.	$695,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 3.14% Airbnb Rental Income: $5064 Traditional Rental Income: $3612 Airbnb ROI: 3.79% Traditional ROI: 3.14%
705 Garden West Ter Winter Garden, FL New Construction by custom builder. Enjoy TRAILSIDE living at it's finest! Garden West is ...	4 beds \| 3 baths \| 2,698 sq.ft.	$1,350,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 0.2% Airbnb Rental Income: $5064 Traditional Rental Income: $2963 Airbnb ROI: 1.05% Traditional ROI: 0.2%
9803 Amber Chestnut Way Winter Garden, FL An incredible energy-efficient Townhouse with a Turnkey package! A Corner Lot Residence wi...	4 beds \| 3 baths \| 2,303 sq.ft.	$535,000	Airbnb cash on cash: 5.07% Traditional cash on cash: 2.62% Airbnb Rental Income: $5064 Traditional Rental Income: $2805 Airbnb ROI: 5.07% Traditional ROI: 2.62%
16137 Wind View Ln Winter Garden, FL DON'T WAIT FOR A NEW BUILT, WHEN YOU CAN PURCHASE THIS AMAZING HOME THAT JUST HIT THE MARK...	4 beds \| 3 baths \| 2,477 sq.ft.	$565,000	Airbnb cash on cash: 5.05% Traditional cash on cash: 4.44% Airbnb Rental Income: $5064 Traditional Rental Income: $3707 Airbnb ROI: 5.05% Traditional ROI: 4.44%
213 W TILDEN STREET Winter Garden, FL Located in DOWNTOWN WINTER GARDEN!! This beautifully renovated single story home combi...	4 beds \| 2 baths \| 2,151 sq.ft.	$765,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 2.24% Airbnb Rental Income: $5064 Traditional Rental Income: $3152 Airbnb ROI: 3.47% Traditional ROI: 2.24%
5531 CYPRESS HILL ROAD Winter Garden, FL Under contract-accepting backup offers. Exquisitely upgraded 4-bedroom, 3-bath smart home ...	4 beds \| 3 baths \| 2,204 sq.ft.	$610,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 3.02% Airbnb Rental Income: $5064 Traditional Rental Income: $3393 Airbnb ROI: 4.14% Traditional ROI: 3.02%
1112 Juniper Hammock Ct Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to this beautiful and spacious 4-b...	4 beds \| 2 baths \| 2,545 sq.ft.	$520,000	Airbnb cash on cash: 5.77% Traditional cash on cash: 3.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3154 Airbnb ROI: 5.77% Traditional ROI: 3.96%
1966 Pantheon Dr Winter Garden, FL Prepare to make new memories in this beautiful 4 bedroom, 3 bathroom home in the heart of ...	4 beds \| 3 baths \| 2,076 sq.ft.	$525,000	Airbnb cash on cash: 5.68% Traditional cash on cash: 2.83% Airbnb Rental Income: $5064 Traditional Rental Income: $2630 Airbnb ROI: 5.68% Traditional ROI: 2.83%
12513 Encore AT Ovation Way Winter Garden, FL Under Construction. Fall in love with this 4-bedroom, 3.5-bath, 2,781 square foot home wit...	4 beds \| 3 baths \| 2,807 sq.ft.	$668,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 4.54% Airbnb Rental Income: $5064 Traditional Rental Income: $3804 Airbnb ROI: 4.91% Traditional ROI: 4.54%
64 N Park Ave Winter Garden, FL Under contract-accepting backup offers. Welcome to the exclusive 30 North Park lifestyle i...	4 beds \| 4 baths \| 2,225 sq.ft.	$1,095,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 2.35% Airbnb Rental Income: $5064 Traditional Rental Income: $3975 Airbnb ROI: 2.41% Traditional ROI: 2.35%
68 N Park Ave Winter Garden, FL Pre-Construction. To be built. Welcome home to The Preserve House @ 30 N. Park â downtow...	4 beds \| 3 baths \| 3,555 sq.ft.	$1,849,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 0.71% Airbnb Rental Income: $5064 Traditional Rental Income: $3406 Airbnb ROI: 1.07% Traditional ROI: 0.71%
15058 SAWGRASS BLUFF DRIVE Winter Garden, FL Under contract-accepting backup offers. Accepting Backup Offers! Location! Location! Loc...	4 beds \| 3 baths \| 2,626 sq.ft.	$579,900	Airbnb cash on cash: 4.85% Traditional cash on cash: 3.43% Airbnb Rental Income: $5064 Traditional Rental Income: $3262 Airbnb ROI: 4.85% Traditional ROI: 3.43%
8031 Navel Orange Ln Winter Garden, FL MOTIVATED SELLER!! BACK ON THE MARKET! Buyer failed to continue with contract; not due to ...	4 beds \| 2 baths \| 2,298 sq.ft.	$659,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 1.87% Airbnb Rental Income: $5064 Traditional Rental Income: $2364 Airbnb ROI: 4.58% Traditional ROI: 1.87%
15381 Honeybell Dr Winter Garden, FL PRICE IMPROVEMENT! Unique opportunity to own a 4BR/3BA Townhome in the heart of the desira...	4 beds \| 3 baths \| 2,034 sq.ft.	$419,000	Airbnb cash on cash: 6.89% Traditional cash on cash: 3.04% Airbnb Rental Income: $5064 Traditional Rental Income: $2520 Airbnb ROI: 6.89% Traditional ROI: 3.04%
16329 Prairie School Dr Winter Garden, FL Impressive interior, Upgraded corner location, Enjoyable front & rear view, and this townh...	4 beds \| 3 baths \| 2,070 sq.ft.	$490,000	Airbnb cash on cash: 6.66% Traditional cash on cash: 5.09% Airbnb Rental Income: $5064 Traditional Rental Income: $3310 Airbnb ROI: 6.66% Traditional ROI: 5.09%
10043 Sequel Aly Winter Garden, FL About 10 minutes to Disney. Corner lot facing open green space. Main floor primary suite w...	4 beds \| 3 baths \| 2,502 sq.ft.	$560,000	Airbnb cash on cash: 4.86% Traditional cash on cash: 4.18% Airbnb Rental Income: $5064 Traditional Rental Income: $3675 Airbnb ROI: 4.86% Traditional ROI: 4.18%
9611 Lost Creek Dr Winter Garden, FL Under contract-accepting backup offers. *SELLER MOTIVATED* $10,000 seller contribution...	4 beds \| 3 baths \| 2,909 sq.ft.	$795,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 2.61% Airbnb Rental Income: $5064 Traditional Rental Income: $3844 Airbnb ROI: 2.86% Traditional ROI: 2.61%
16012 Micelli Dr Winter Garden, FL Welcome to this beautifully designed 2021-built 4-bedroom, 3-bathroom plus a bonus room co...	4 beds \| 3 baths \| 2,428 sq.ft.	$699,000	Airbnb cash on cash: 3.77% Traditional cash on cash: 2.9% Airbnb Rental Income: $5064 Traditional Rental Income: $3463 Airbnb ROI: 3.77% Traditional ROI: 2.9%
10705 PETRILLO WAY Winter Garden, FL Under contract-accepting backup offers. Set against stunning private CONSERVATION VIEWS th...	4 beds \| 3 baths \| 2,528 sq.ft.	$725,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 2.52% Airbnb Rental Income: $5064 Traditional Rental Income: $3507 Airbnb ROI: 3.3% Traditional ROI: 2.52%
15444 LEBEAU LOOP Winter Garden, FL Under contract-accepting backup offers. Newer 2024 build, this 4-bedroom home features thr...	4 beds \| 4 baths \| 2,415 sq.ft.	$580,000	Airbnb cash on cash: 5.73% Traditional cash on cash: 5.05% Airbnb Rental Income: $5064 Traditional Rental Income: $3663 Airbnb ROI: 5.73% Traditional ROI: 5.05%
17059 Harbor Oak Pkwy Winter Garden, FL Welcome to this beautiful, well-maintained home located in the Waterside Community at 1705...	4 beds \| 3 baths \| 2,692 sq.ft.	$635,500	Airbnb cash on cash: 3.84% Traditional cash on cash: 2.83% Airbnb Rental Income: $5064 Traditional Rental Income: $3433 Airbnb ROI: 3.84% Traditional ROI: 2.83%
9201 Gran Teatro Dr Winter Garden, FL Under Construction. The Windham townhome is 1833 sq ft and offers 3 bedrooms, a flex, 2.5 ...	4 beds \| 3 baths \| 1,715 sq.ft.	$525,000	Airbnb cash on cash: 5.19% Traditional cash on cash: 2.68% Airbnb Rental Income: $5064 Traditional Rental Income: $2797 Airbnb ROI: 5.19% Traditional ROI: 2.68%
11187 Hanlon Terrace Aly Winter Garden, FL Welcome to this beautifully maintained two-story townhouse in the heart of Winter Garden, ...	4 beds \| 3 baths \| 2,200 sq.ft.	$399,900	Airbnb cash on cash: 6.56% Traditional cash on cash: 4.73% Airbnb Rental Income: $5064 Traditional Rental Income: $3320 Airbnb ROI: 6.56% Traditional ROI: 4.73%
8906 DODDINGTON WAY Winter Garden, FL Under contract-accepting backup offers. ***This house comes with a REDUCED RATE through th...	4 beds \| 3 baths \| 2,352 sq.ft.	$550,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 3.73% Airbnb Rental Income: $5064 Traditional Rental Income: $3488 Airbnb ROI: 4.78% Traditional ROI: 3.73%
1674 Victoria Way Winter Garden, FL Beautifully updated POOL home in the desirable Tuscany community! Major updates include a ...	4 beds \| 2 baths \| 2,239 sq.ft.	$659,990	Airbnb cash on cash: 4.39% Traditional cash on cash: 4.25% Airbnb Rental Income: $5064 Traditional Rental Income: $3947 Airbnb ROI: 4.39% Traditional ROI: 4.25%
14075 Lochend Way Winter Garden, FL Under contract-accepting backup offers. Stunning BRAND NEW CORNER TH, Never-Before-Lived-I...	4 beds \| 3 baths \| 2,197 sq.ft.	$534,999	Airbnb cash on cash: 6.36% Traditional cash on cash: 4.5% Airbnb Rental Income: $5064 Traditional Rental Income: $3099 Airbnb ROI: 6.36% Traditional ROI: 4.5%
17058 Quicksilver Ave Winter Garden, FL for sale	4 beds \| 3 baths \| 2,492 sq.ft.	$539,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 3.75% Airbnb Rental Income: $5064 Traditional Rental Income: $3381 Airbnb ROI: 5.04% Traditional ROI: 3.75%
512 Garden Heights Dr Winter Garden, FL Under contract-accepting backup offers. Welcome to your dream home! This beautifully updat...	4 beds \| 2 baths \| 1,700 sq.ft.	$564,900	Airbnb cash on cash: 5.81% Traditional cash on cash: 3.34% Airbnb Rental Income: $5064 Traditional Rental Income: $2727 Airbnb ROI: 5.81% Traditional ROI: 3.34%
15543 PEBBLE RIDGE STREET Winter Garden, FL Under contract-accepting backup offers. Popular Stoneybrook West Subdivision - A gated gol...	4 beds \| 3 baths \| 3,359 sq.ft.	$645,900	Airbnb cash on cash: 3.79% Traditional cash on cash: 3.04% Airbnb Rental Income: $5064 Traditional Rental Income: $3576 Airbnb ROI: 3.79% Traditional ROI: 3.04%
6560 CANDIED PEEL ALLEY Winter Garden, FL BEAUTIFUL 4 bedrooms and 3 bathrooms townhouse located in new Winter Garden area, the kit...	4 beds \| 4 baths \| 1,902 sq.ft.	$410,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 4.77% Airbnb Rental Income: $5064 Traditional Rental Income: $3297 Airbnb ROI: 6.68% Traditional ROI: 4.77%

Vacation Rentals in Winter Garden

There are 314 vacation rental properties available for sale in the city of Winter Garden . The median list price of Airbnb properties available for sale in Winter Garden is $625,580 and the average price per square foot is $259. The cash on cash return on vacation rentals in Winter Garden is 1.00%. The average monthly short term rental income in Winter Garden is $2,390.

Winter Garden, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 314 Airbnb properties available for sale in Winter Garden.

In 2026, the best neighborhood to buy short term rental property is Winter Garden.

In May 2026, the average Airbnb occupancy rate in Winter Garden is 78%.

Airbnb data on vacation rentals in Winter Garden, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter Garden, FL market insights, guest information and booking details, seasonality trends and historical Winter Garden, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Winter Garden, FL

13836 Daniels Landing Cir

Winter Garden, FL

2 beds | 2 baths | 1,234 sq.ft.

$300,000

Airbnb cash on cash: 2.98%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $2340

Traditional Rental Income: $1660

Airbnb ROI: 2.98%

Traditional ROI: 2.63%

264 BLUE STONE CIRCLE

Winter Garden, FL

4 beds | 3 baths | 2,538 sq.ft.

$725,000

Airbnb cash on cash: 4.02%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $5064

Traditional Rental Income: $3698

Airbnb ROI: 4.02%

Traditional ROI: 3.53%

15558 Sandfield Loop

Winter Garden, FL

4 beds | 3 baths | 4,307 sq.ft.

$765,000

Airbnb cash on cash: 3.49%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $5064

Traditional Rental Income: $3134

Airbnb ROI: 3.49%

Traditional ROI: 2.23%

14844 Driftwater Dr

Winter Garden, FL

4 beds | 2 baths | 1,990 sq.ft.

$429,990

Airbnb cash on cash: 6.69%

Traditional cash on cash: 2.53%

Airbnb Rental Income: $5064

Traditional Rental Income: $2356

Airbnb ROI: 6.69%

Traditional ROI: 2.53%

897 Landrum Dr

Winter Garden, FL

4 beds | 3 baths | 3,012 sq.ft.

$899,900

Airbnb cash on cash: 2.73%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $5064

Traditional Rental Income: $3383

Airbnb ROI: 2.73%

Traditional ROI: 1.96%

9338 Tyrella Pine Trl

Winter Garden, FL

4 beds | 2 baths | 1,696 sq.ft.

$449,000

Airbnb cash on cash: 7.75%

Traditional cash on cash: 4.89%

Airbnb Rental Income: $5064

Traditional Rental Income: $2829

Airbnb ROI: 7.75%

Traditional ROI: 4.89%

7832 Freestyle Ln

Winter Garden, FL

4 beds | 3 baths | 2,650 sq.ft.

$1,075,000

Airbnb cash on cash: 2.44%

Traditional cash on cash: 1.44%

Airbnb Rental Income: $5064

Traditional Rental Income: $3030

Airbnb ROI: 2.44%

Traditional ROI: 1.44%

261 Zachary Wade St

Winter Garden, FL

4 beds | 3 baths | 3,728 sq.ft.

$1,699,000

Airbnb cash on cash: 0.96%

Traditional cash on cash: 0.65%

Airbnb Rental Income: $5064

Traditional Rental Income: $3554

Airbnb ROI: 0.96%