Airbnb Properties for Sale in Longwood, FL

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

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

Airbnb For Sale in Longwood, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
211 FAIRWAY DRIVE #211 Longwood, FL Welcome to this charming condo located in the highly sought-after, gated community of The ...	3 beds \| 2 baths \| 1,496 sq.ft.	$187,500	Airbnb cash on cash: 7.73% Traditional cash on cash: 5.4% Airbnb Rental Income: $3221 Traditional Rental Income: $2080 Airbnb ROI: 7.73% Traditional ROI: 5.4%
899 LORMANN CIRCLE Longwood, FL Welcome to your Longwood retreat. Enjoy the peace of mind that comes with no HOA! This me...	3 beds \| 2 baths \| 969 sq.ft.	$299,490	Airbnb cash on cash: 7.12% Traditional cash on cash: 4.66% Airbnb Rental Income: $3221 Traditional Rental Income: $1803 Airbnb ROI: 7.12% Traditional ROI: 4.66%
364 HOWARD BOULEVARD Longwood, FL Under contract-accepting backup offers. Welcome to this charming 3-bedroom, 2-bath home tu...	3 beds \| 2 baths \| 1,428 sq.ft.	$370,000	Airbnb cash on cash: 5.33% Traditional cash on cash: 4.26% Airbnb Rental Income: $3221 Traditional Rental Income: $2122 Airbnb ROI: 5.33% Traditional ROI: 4.26%
449 SPRINGWOOD COURT Longwood, FL Under contract-accepting backup offers. This beautifully updated three-bedroom, two-bath h...	3 beds \| 2 baths \| 1,075 sq.ft.	$317,500	Airbnb cash on cash: 5.99% Traditional cash on cash: 3.78% Airbnb Rental Income: $3221 Traditional Rental Income: $1834 Airbnb ROI: 5.99% Traditional ROI: 3.78%
162 DUNCAN TRAIL Longwood, FL Under contract-accepting backup offers. Step into this updated 4-bed, 2-bath home that sit...	4 beds \| 2 baths \| 1,907 sq.ft.	$450,000	Airbnb cash on cash: 8.09% Traditional cash on cash: 3.76% Airbnb Rental Income: $5377 Traditional Rental Income: $2468 Airbnb ROI: 8.09% Traditional ROI: 3.76%
230 HOWARD BOULEVARD Longwood, FL Welcome to this beautifully updated 3-bedroom, 2-bath single-family home located in the he...	3 beds \| 2 baths \| 1,173 sq.ft.	$262,000	Airbnb cash on cash: 7.54% Traditional cash on cash: 5.43% Airbnb Rental Income: $3221 Traditional Rental Income: $1973 Airbnb ROI: 7.54% Traditional ROI: 5.43%
1889 RANCHLAND TRAIL Longwood, FL Exquisite 4-Bedroom Estate with Pool on 2+ Acres in the Coveted LongwoodâLake Mary Area,...	4 beds \| 3 baths \| 2,333 sq.ft.	$989,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 1.83% Airbnb Rental Income: $5377 Traditional Rental Income: $3252 Airbnb ROI: 2.96% Traditional ROI: 1.83%
4 WOODEN SHOE LANE Longwood, FL Under contract-accepting backup offers. Short Sale. Must See 4 bed, 2 bath home in the est...	4 beds \| 2 baths \| 2,682 sq.ft.	$350,000	Airbnb cash on cash: 9.51% Traditional cash on cash: 5.03% Airbnb Rental Income: $5377 Traditional Rental Income: $2819 Airbnb ROI: 9.51% Traditional ROI: 5.03%
210 BANBURY COURT Longwood, FL New Improved Price! Your new pool home in the desirable Wekiva Hills community is waiting ...	4 beds \| 2 baths \| 2,720 sq.ft.	$450,000	Airbnb cash on cash: 8.82% Traditional cash on cash: 6.28% Airbnb Rental Income: $5377 Traditional Rental Income: $3220 Airbnb ROI: 8.82% Traditional ROI: 6.28%
358 WINCHESTER COURT Longwood, FL Seller Motivated Closing cost, rate buy down incentives being offered or You can buy ...	3 beds \| 3 baths \| 1,682 sq.ft.	$319,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 2.78% Airbnb Rental Income: $3221 Traditional Rental Income: $2181 Airbnb ROI: 3.82% Traditional ROI: 2.78%
150 ESSEX DRIVE Longwood, FL Step into the warmth and charm of this rare cabin-style retreat nestled in the heart of Lo...	3 beds \| 2 baths \| 1,449 sq.ft.	$432,000	Airbnb cash on cash: 3.89% Traditional cash on cash: 3.16% Airbnb Rental Income: $3221 Traditional Rental Income: $2199 Airbnb ROI: 3.89% Traditional ROI: 3.16%
501 RIVERBEND BOULEVARD Longwood, FL Under contract-accepting backup offers. Are you ready to finally add the most important ke...	4 beds \| 2 baths \| 2,559 sq.ft.	$583,000	Airbnb cash on cash: 5.41% Traditional cash on cash: 2.71% Airbnb Rental Income: $5377 Traditional Rental Income: $2824 Airbnb ROI: 5.41% Traditional ROI: 2.71%
674 PINE SHADOW COURT Longwood, FL Under contract-accepting backup offers. Discover this beautifully maintained 4-bedroom, 3-...	4 beds \| 3 baths \| 2,754 sq.ft.	$710,000	Airbnb cash on cash: 4.75% Traditional cash on cash: 3.41% Airbnb Rental Income: $5377 Traditional Rental Income: $3403 Airbnb ROI: 4.75% Traditional ROI: 3.41%
2010 E Triangle Drive Longwood, FL Step Inside Your Future Home! This beautiful 3-bedroom, 2-bath, 1,684 sq ft home has been ...	3 beds \| 2 baths \| 1,684 sq.ft.	$349,900	Airbnb cash on cash: 5.36% Traditional cash on cash: 4.89% Airbnb Rental Income: $3221 Traditional Rental Income: $2342 Airbnb ROI: 5.36% Traditional ROI: 4.89%
851 N WAYMAN STREET Longwood, FL Under contract-accepting backup offers. Welcome to this beautifully updated Longwood pool ...	3 beds \| 2 baths \| 1,353 sq.ft.	$360,000	Airbnb cash on cash: 5.88% Traditional cash on cash: 4.89% Airbnb Rental Income: $3221 Traditional Rental Income: $2160 Airbnb ROI: 5.88% Traditional ROI: 4.89%
430 BRASSIE DRIVE Longwood, FL This 4-bed 3 bathroom home in Longwood offers multi-generational flexibility, over 2,500 s...	4 beds \| 3 baths \| 2,537 sq.ft.	$550,000	Airbnb cash on cash: 6.78% Traditional cash on cash: 4.61% Airbnb Rental Income: $5377 Traditional Rental Income: $3177 Airbnb ROI: 6.78% Traditional ROI: 4.61%
572 LAKE WILDMERE COVE Longwood, FL Here is your opportunity to own a true Turn Key Investment property.This almost new townho...	4 beds \| 5 baths \| 2,294 sq.ft.	$455,000	Airbnb cash on cash: 6.54% Traditional cash on cash: 4.01% Airbnb Rental Income: $5377 Traditional Rental Income: $3213 Airbnb ROI: 6.54% Traditional ROI: 4.01%
1510 PELICAN STREET Longwood, FL Under contract-accepting backup offers. 3-bed, 2-bath residence nestled on a serene, tree-...	3 beds \| 2 baths \| 1,269 sq.ft.	$268,900	Airbnb cash on cash: 6.8% Traditional cash on cash: 4.74% Airbnb Rental Income: $3221 Traditional Rental Income: $1973 Airbnb ROI: 6.8% Traditional ROI: 4.74%
1821 STANLEY STREET Longwood, FL Under contract-accepting backup offers. Welcome to this charming and spacious home tucked ...	3 beds \| 2 baths \| 2,567 sq.ft.	$485,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 3.53% Airbnb Rental Income: $3221 Traditional Rental Income: $2427 Airbnb ROI: 3.68% Traditional ROI: 3.53%
322 N SHADOWBAY BOULEVARD Longwood, FL Welcome to Lake Vista at Shadowbay - No HOA and No Restrictions! This beautiful and well-m...	3 beds \| 2 baths \| 1,599 sq.ft.	$525,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 3.25% Airbnb Rental Income: $3221 Traditional Rental Income: $2395 Airbnb ROI: 3.45% Traditional ROI: 3.25%
1581 MONICA JOY CIRCLE Longwood, FL Located in TOP RATED SEMINOLE COUNTY SCHOOL DISTRICT. Single story ranch home on a cul de ...	4 beds \| 2 baths \| 2,073 sq.ft.	$469,900	Airbnb cash on cash: 7.97% Traditional cash on cash: 4.04% Airbnb Rental Income: $5377 Traditional Rental Income: $2564 Airbnb ROI: 7.97% Traditional ROI: 4.04%
975 CROSS CUT WAY Longwood, FL Beautiful 4 bedroom 2.5 bathroom home Freshly Painted with Luxury Vinyl flooring and Stain...	4 beds \| 3 baths \| 2,289 sq.ft.	$470,000	Airbnb cash on cash: 7.17% Traditional cash on cash: 4.19% Airbnb Rental Income: $5377 Traditional Rental Income: $2982 Airbnb ROI: 7.17% Traditional ROI: 4.19%
2330 PLEASANT DRIVE Longwood, FL One or more photo(s) has been virtually staged. Completely renovated and move-in ready, th...	3 beds \| 2 baths \| 1,311 sq.ft.	$395,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 5.03% Airbnb Rental Income: $3221 Traditional Rental Income: $2491 Airbnb ROI: 5.04% Traditional ROI: 5.03%
420 SUMMIT RIDGE PLACE #200 Longwood, FL **This property qualifies for a closing cost credit up to $3,700 through the Sellerâs pr...	3 beds \| 2 baths \| 1,586 sq.ft.	$239,000	Airbnb cash on cash: 5.6% Traditional cash on cash: 4.03% Airbnb Rental Income: $3221 Traditional Rental Income: $2141 Airbnb ROI: 5.6% Traditional ROI: 4.03%
117 MYRTLE STREET Longwood, FL LOCATION, LOCATION, LOCATION !!! Welcome home to this stylish and newly built 3-bedroom...	3 beds \| 3 baths \| 1,488 sq.ft.	$379,000	Airbnb cash on cash: 4% Traditional cash on cash: 2.99% Airbnb Rental Income: $3221 Traditional Rental Income: $2135 Airbnb ROI: 4% Traditional ROI: 2.99%
170 CLYDE AVENUE Longwood, FL This beautifully renovated 3-bedroom, 2-bath home features fresh interior and exterior pai...	3 beds \| 2 baths \| 1,658 sq.ft.	$404,900	Airbnb cash on cash: 5.12% Traditional cash on cash: 5.04% Airbnb Rental Income: $3221 Traditional Rental Income: $2465 Airbnb ROI: 5.12% Traditional ROI: 5.04%
635 CAMBRIDGE COURT Longwood, FL Under contract-accepting backup offers. Your Dream Home Awaits! Owner Financing Opportunit...	4 beds \| 2 baths \| 1,938 sq.ft.	$479,000	Airbnb cash on cash: 6.98% Traditional cash on cash: 3.78% Airbnb Rental Income: $5377 Traditional Rental Income: $2856 Airbnb ROI: 6.98% Traditional ROI: 3.78%
942 MALDEN COURT Longwood, FL Back on the Market with new interior paint, new flooring in the bedrooms and new bathroom ...	3 beds \| 2 baths \| 1,491 sq.ft.	$300,000	Airbnb cash on cash: 5.89% Traditional cash on cash: 4.77% Airbnb Rental Income: $3221 Traditional Rental Income: $2177 Airbnb ROI: 5.89% Traditional ROI: 4.77%
2745 Night Hawk Ct. Longwood, FL Don't miss out on this opportunity to own a 3 bedroom, 2 bath townhouse in Shadowbay Club....	3 beds \| 2 baths \| 1,396 sq.ft.	$360,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 3.67% Airbnb Rental Income: $3221 Traditional Rental Income: $2051 Airbnb ROI: 4.99% Traditional ROI: 3.67%
1221 ARDEN STREET Longwood, FL Under contract-accepting backup offers. WOWSA! Pool homes with this kind of layout, amenit...	3 beds \| 2 baths \| 1,525 sq.ft.	$448,875	Airbnb cash on cash: 4.31% Traditional cash on cash: 4.03% Airbnb Rental Income: $3221 Traditional Rental Income: $2374 Airbnb ROI: 4.31% Traditional ROI: 4.03%
290 QUEENSBERRY COURT Longwood, FL NEW ROOF (see new ext pictures). Beautifully remodeled 3-bedroom, 2-bath home perfectly si...	3 beds \| 2 baths \| 2,066 sq.ft.	$499,900	Airbnb cash on cash: 3.74% Traditional cash on cash: 3.72% Airbnb Rental Income: $3221 Traditional Rental Income: $2486 Airbnb ROI: 3.74% Traditional ROI: 3.72%
495 HOWARD AVENUE Longwood, FL Welcome to your dream home! This stunning 4-bedroom, 2-bathroom residence has been complet...	4 beds \| 2 baths \| 1,855 sq.ft.	$424,999	Airbnb cash on cash: 8.98% Traditional cash on cash: 4.54% Airbnb Rental Income: $5377 Traditional Rental Income: $2527 Airbnb ROI: 8.98% Traditional ROI: 4.54%
204 ADAIR AVENUE Longwood, FL REDUCED FOR QUICK SALE! Charming 4 bedroom, 3 bathroom remodeled POOL home with a screened...	4 beds \| 3 baths \| 2,606 sq.ft.	$624,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 5.06% Airbnb Rental Income: $5377 Traditional Rental Income: $3666 Airbnb ROI: 6.13% Traditional ROI: 5.06%
140 W YORK COURT Longwood, FL One or more photo(s) has been virtually staged. Welcome to a home that feels like it was w...	4 beds \| 3 baths \| 2,047 sq.ft.	$469,000	Airbnb cash on cash: 8.12% Traditional cash on cash: 5.48% Airbnb Rental Income: $5377 Traditional Rental Income: $3135 Airbnb ROI: 8.12% Traditional ROI: 5.48%
1823 NORTH STREET Longwood, FL Under contract-accepting backup offers. Your search ends here with this exceptional, one-o...	3 beds \| 2 baths \| 1,650 sq.ft.	$399,900	Airbnb cash on cash: 4.97% Traditional cash on cash: 4.33% Airbnb Rental Income: $3221 Traditional Rental Income: $2255 Airbnb ROI: 4.97% Traditional ROI: 4.33%
665 E CHURCH AVENUE Longwood, FL Excellent for first time home buyers. Cozy renovated 3 Bedroom 1 Bath Home in Longwood nea...	3 beds \| 1 baths \| 836 sq.ft.	$244,000	Airbnb cash on cash: 8.73% Traditional cash on cash: 4.7% Airbnb Rental Income: $3221 Traditional Rental Income: $1565 Airbnb ROI: 8.73% Traditional ROI: 4.7%
300 N SHADOWBAY BOULEVARD #204 Longwood, FL Under contract-accepting backup offers. Spacious Condo with Rooftop Lake Views. Experience...	3 beds \| 3 baths \| 1,760 sq.ft.	$285,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 4.86% Airbnb Rental Income: $3221 Traditional Rental Income: $2460 Airbnb ROI: 4.99% Traditional ROI: 4.86%
1803 MISTY MORN PLACE Longwood, FL Tucked away along the sought-after Markham Woods corridor, this beautifully maintained cus...	4 beds \| 3 baths \| 2,881 sq.ft.	$849,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 2.5% Airbnb Rental Income: $5377 Traditional Rental Income: $3313 Airbnb ROI: 3.74% Traditional ROI: 2.5%
672 MOSSY BRANCH COURT Longwood, FL Completely remodeled and move-in ready, this impressive residence at 672 Mossy Branch Ct, ...	4 beds \| 3 baths \| 3,924 sq.ft.	$799,900	Airbnb cash on cash: 4.03% Traditional cash on cash: 2.63% Airbnb Rental Income: $5377 Traditional Rental Income: $3249 Airbnb ROI: 4.03% Traditional ROI: 2.63%
230 W SABAL PALM PLACE Longwood, FL Welcome to the highly sought after, wonderfully located community of San Marco Villas in t...	3 beds \| 2 baths \| 1,484 sq.ft.	$225,000	Airbnb cash on cash: 7.58% Traditional cash on cash: 5.63% Airbnb Rental Income: $3221 Traditional Rental Income: $2079 Airbnb ROI: 7.58% Traditional ROI: 5.63%

Vacation Rentals in Longwood

There are 73 vacation rental properties available for sale in the city of Longwood . The median list price of Airbnb properties available for sale in Longwood is $428,500 and the average price per square foot is $206. The cash on cash return on vacation rentals in Longwood is 4.00%. The average monthly short term rental income in Longwood is $3,221.

Longwood, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 73 Airbnb properties available for sale in Longwood.

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

In January 2026, the average Airbnb occupancy rate in Longwood is 53%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Longwood, FL

211 FAIRWAY DRIVE #211

Longwood, FL

3 beds | 2 baths | 1,496 sq.ft.

$187,500

Airbnb cash on cash: 7.73%

Traditional cash on cash: 5.4%

Airbnb Rental Income: $3221

Traditional Rental Income: $2080

Airbnb ROI: 7.73%

Traditional ROI: 5.4%

899 LORMANN CIRCLE

Longwood, FL

3 beds | 2 baths | 969 sq.ft.

$299,490

Airbnb cash on cash: 7.12%

Traditional cash on cash: 4.66%

Airbnb Rental Income: $3221

Traditional Rental Income: $1803

Airbnb ROI: 7.12%

Traditional ROI: 4.66%

364 HOWARD BOULEVARD

Longwood, FL

3 beds | 2 baths | 1,428 sq.ft.

$370,000

Airbnb cash on cash: 5.33%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $3221

Traditional Rental Income: $2122

Airbnb ROI: 5.33%

Traditional ROI: 4.26%

449 SPRINGWOOD COURT

Longwood, FL

3 beds | 2 baths | 1,075 sq.ft.

$317,500

Airbnb cash on cash: 5.99%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $3221

Traditional Rental Income: $1834

Airbnb ROI: 5.99%

Traditional ROI: 3.78%

162 DUNCAN TRAIL

Longwood, FL

4 beds | 2 baths | 1,907 sq.ft.

$450,000

Airbnb cash on cash: 8.09%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $5377

Traditional Rental Income: $2468

Airbnb ROI: 8.09%

Traditional ROI: 3.76%

230 HOWARD BOULEVARD

Longwood, FL

3 beds | 2 baths | 1,173 sq.ft.

$262,000

Airbnb cash on cash: 7.54%

Traditional cash on cash: 5.43%

Airbnb Rental Income: $3221

Traditional Rental Income: $1973

Airbnb ROI: 7.54%

Traditional ROI: 5.43%

1889 RANCHLAND TRAIL

Longwood, FL

4 beds | 3 baths | 2,333 sq.ft.

$989,000

Airbnb cash on cash: 2.96%

Traditional cash on cash: 1.83%

Airbnb Rental Income: $5377

Traditional Rental Income: $3252

Airbnb ROI: 2.96%

Traditional ROI: 1.83%

4 WOODEN SHOE LANE

Longwood, FL

4 beds | 2 baths | 2,682 sq.ft.

$350,000

Airbnb cash on cash: 9.51%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $5377

Traditional Rental Income: $2819

Airbnb ROI: 9.51%