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.	$289,990	Airbnb cash on cash: 7.38% Traditional cash on cash: 4.84% Airbnb Rental Income: $3221 Traditional Rental Income: $1803 Airbnb ROI: 7.38% Traditional ROI: 4.84%
199 E MARVIN AVENUE Longwood, FL Under contract-accepting backup offers. Come see this spacious, updated First time Homebuy...	3 beds \| 1 baths \| 967 sq.ft.	$265,000	Airbnb cash on cash: 7.76% Traditional cash on cash: 4.53% Airbnb Rental Income: $3221 Traditional Rental Income: $1686 Airbnb ROI: 7.76% Traditional ROI: 4.53%
2681 AZALEA DRIVE Longwood, FL A Home to Be Thankful For â $10,000 in Buyer Savings! As the season turns and the air...	3 beds \| 2 baths \| 1,399 sq.ft.	$365,000	Airbnb cash on cash: 4.94% Traditional cash on cash: 3.48% Airbnb Rental Income: $3221 Traditional Rental Income: $1994 Airbnb ROI: 4.94% Traditional ROI: 3.48%
364 HOWARD BOULEVARD Longwood, FL Welcome to this charming 3-bedroom, 2-bath home tucked away at the end of a quiet dead-end...	3 beds \| 2 baths \| 1,400 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%
1530 ARDEN STREET Longwood, FL Under contract-accepting backup offers. Fall in love with this beautifully updated 4-bedro...	4 beds \| 2 baths \| 1,840 sq.ft.	$399,000	Airbnb cash on cash: 9.45% Traditional cash on cash: 4.79% Airbnb Rental Income: $5377 Traditional Rental Income: $2551 Airbnb ROI: 9.45% Traditional ROI: 4.79%
449 SPRINGWOOD COURT Longwood, FL This beautifully updated three-bedroom, two-bath home in Longwood offers 1,075 square feet...	3 beds \| 2 baths \| 1,075 sq.ft.	$325,000	Airbnb cash on cash: 5.83% Traditional cash on cash: 3.67% Airbnb Rental Income: $3221 Traditional Rental Income: $1834 Airbnb ROI: 5.83% Traditional ROI: 3.67%
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%
104 N SILVER CLUSTER COURT Longwood, FL Under contract-accepting backup offers. Seller may consider buyer concessions if made in a...	3 beds \| 2 baths \| 1,386 sq.ft.	$395,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 3.41% Airbnb Rental Income: $3221 Traditional Rental Income: $2089 Airbnb ROI: 4.51% Traditional ROI: 3.41%
2040 E TRIANGLE DRIVE Longwood, FL NEW PRICE REDUCTION! Now priced below market value. Charming, Updated 3-Bedroom Home ...	3 beds \| 2 baths \| 1,283 sq.ft.	$345,000	Airbnb cash on cash: 5.42% Traditional cash on cash: 3.62% Airbnb Rental Income: $3221 Traditional Rental Income: $1912 Airbnb ROI: 5.42% Traditional ROI: 3.62%
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 Your new pool home in the desirable Wekiva Hills community is waiting for you. This 4 bedr...	4 beds \| 2 baths \| 2,720 sq.ft.	$470,000	Airbnb cash on cash: 8.41% Traditional cash on cash: 5.97% Airbnb Rental Income: $5377 Traditional Rental Income: $3220 Airbnb ROI: 8.41% Traditional ROI: 5.97%
358 WINCHESTER COURT Longwood, FL Under contract-accepting backup offers. Seller Motivated Closing cost, rate buy down ...	3 beds \| 3 baths \| 1,682 sq.ft.	$335,000	Airbnb cash on cash: 3.6% Traditional cash on cash: 2.6% Airbnb Rental Income: $3221 Traditional Rental Income: $2181 Airbnb ROI: 3.6% Traditional ROI: 2.6%
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.	$440,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 3.08% Airbnb Rental Income: $3221 Traditional Rental Income: $2199 Airbnb ROI: 3.8% Traditional ROI: 3.08%
501 RIVERBEND BOULEVARD Longwood, FL Are you ready to finally add the most important key to your keychain? After scrolling for...	4 beds \| 2 baths \| 2,559 sq.ft.	$599,900	Airbnb cash on cash: 5.23% Traditional cash on cash: 2.61% Airbnb Rental Income: $5377 Traditional Rental Income: $2824 Airbnb ROI: 5.23% Traditional ROI: 2.61%
674 PINE SHADOW COURT Longwood, FL Discover this beautifully maintained 4-bedroom, 3-bath home in the sought-after Sabal Poin...	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%
917 BRANTLEY DRIVE Longwood, FL Under contract-accepting backup offers. Beautifully updated 4-bedroom, 2.5-bath home in on...	4 beds \| 3 baths \| 2,413 sq.ft.	$500,000	Airbnb cash on cash: 7.07% Traditional cash on cash: 4.26% Airbnb Rental Income: $5377 Traditional Rental Income: $2976 Airbnb ROI: 7.07% Traditional ROI: 4.26%
851 N WAYMAN STREET Longwood, FL Welcome to this beautifully updated Longwood pool home full of charm, warmth, and timeless...	3 beds \| 2 baths \| 1,353 sq.ft.	$362,500	Airbnb cash on cash: 5.83% Traditional cash on cash: 4.85% Airbnb Rental Income: $3221 Traditional Rental Income: $2160 Airbnb ROI: 5.83% Traditional ROI: 4.85%
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%
115 FOREST POINT LANE Longwood, FL Under contract-accepting backup offers. Welcome to 115 Forest Point Lane â a beautifully...	4 beds \| 3 baths \| 2,689 sq.ft.	$875,000	Airbnb cash on cash: 3.65% Traditional cash on cash: 2.61% Airbnb Rental Income: $5377 Traditional Rental Income: $3443 Airbnb ROI: 3.65% Traditional ROI: 2.61%
1510 PELICAN STREET Longwood, FL 3-bed, 2-bath residence nestled on a serene, tree-lined street in one of Longwoodâs DESI...	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 Welcome to this charming and spacious home tucked away in the sought-after Sanlando Spring...	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%
102 TOMOKA TRAIL #102 Longwood, FL New Roof 10/25! This gem of a condo is ready for you to make it your new home in the oasi...	3 beds \| 2 baths \| 1,590 sq.ft.	$275,000	Airbnb cash on cash: 7.03% Traditional cash on cash: 5.69% Airbnb Rental Income: $3221 Traditional Rental Income: $2147 Airbnb ROI: 7.03% Traditional ROI: 5.69%
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.	$410,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 4.81% Airbnb Rental Income: $3221 Traditional Rental Income: $2491 Airbnb ROI: 4.82% Traditional ROI: 4.81%
821 SUTTER LOOP Longwood, FL Under contract-accepting backup offers. NEW PRICE IMPROVEMENT SEPT 19!, NEW ROOF April 202...	4 beds \| 2 baths \| 2,074 sq.ft.	$430,000	Airbnb cash on cash: 8.82% Traditional cash on cash: 4.75% Airbnb Rental Income: $5377 Traditional Rental Income: $2655 Airbnb ROI: 8.82% Traditional ROI: 4.75%
287 HILLTOP DRIVE Longwood, FL Under contract-accepting backup offers. Convenience, Land, Nature, Energy Efficiency. Keep...	4 beds \| 3 baths \| 2,522 sq.ft.	$575,000	Airbnb cash on cash: 6.32% Traditional cash on cash: 3.5% Airbnb Rental Income: $5377 Traditional Rental Income: $2780 Airbnb ROI: 6.32% Traditional ROI: 3.5%
193 E WARREN AVENUE Longwood, FL Pristine 2023-Built Townhome in Monterey Community â Minutes to SunRail & Historic Longw...	3 beds \| 3 baths \| 1,488 sq.ft.	$379,900	Airbnb cash on cash: 4.16% Traditional cash on cash: 3.15% Airbnb Rental Income: $3221 Traditional Rental Income: $2135 Airbnb ROI: 4.16% Traditional ROI: 3.15%
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.	$385,000	Airbnb cash on cash: 3.93% Traditional cash on cash: 2.93% Airbnb Rental Income: $3221 Traditional Rental Income: $2135 Airbnb ROI: 3.93% Traditional ROI: 2.93%
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.	$409,900	Airbnb cash on cash: 5.05% Traditional cash on cash: 4.97% Airbnb Rental Income: $3221 Traditional Rental Income: $2465 Airbnb ROI: 5.05% Traditional ROI: 4.97%
635 CAMBRIDGE COURT Longwood, FL Your Dream Home Awaits! Owner Financing Opportunity! Tired of Bank Hassle? Ready to Own N...	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.	$325,000	Airbnb cash on cash: 5.37% Traditional cash on cash: 4.33% Airbnb Rental Income: $3221 Traditional Rental Income: $2177 Airbnb ROI: 5.37% Traditional ROI: 4.33%
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 WOWSA! Pool homes with this kind of layout, amenities, & functionality rarely hit the mark...	3 beds \| 2 baths \| 1,525 sq.ft.	$450,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 4.01% Airbnb Rental Income: $3221 Traditional Rental Income: $2374 Airbnb ROI: 4.3% Traditional ROI: 4.01%
1681 OVERLOOK ROAD Longwood, FL One or more photo(s) has been virtually staged. Charming 4-bedroom, 2-bath home situated i...	4 beds \| 2 baths \| 1,722 sq.ft.	$435,000	Airbnb cash on cash: 8.9% Traditional cash on cash: 4.2% Airbnb Rental Income: $5377 Traditional Rental Income: $2376 Airbnb ROI: 8.9% Traditional ROI: 4.2%

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 $426,350 and the average price per square foot is $207. 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 2025, the best neighborhood to buy short term rental property is Longwood.

In November 2025, 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.

$289,990

Airbnb cash on cash: 7.38%

Traditional cash on cash: 4.84%

Airbnb Rental Income: $3221

Traditional Rental Income: $1803

Airbnb ROI: 7.38%

Traditional ROI: 4.84%

199 E MARVIN AVENUE

Longwood, FL

3 beds | 1 baths | 967 sq.ft.

$265,000

Airbnb cash on cash: 7.76%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $3221

Traditional Rental Income: $1686

Airbnb ROI: 7.76%

Traditional ROI: 4.53%

2681 AZALEA DRIVE

Longwood, FL

3 beds | 2 baths | 1,399 sq.ft.

$365,000

Airbnb cash on cash: 4.94%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $3221

Traditional Rental Income: $1994

Airbnb ROI: 4.94%

Traditional ROI: 3.48%

364 HOWARD BOULEVARD

Longwood, FL

3 beds | 2 baths | 1,400 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%

1530 ARDEN STREET

Longwood, FL

4 beds | 2 baths | 1,840 sq.ft.

$399,000

Airbnb cash on cash: 9.45%

Traditional cash on cash: 4.79%

Airbnb Rental Income: $5377

Traditional Rental Income: $2551

Airbnb ROI: 9.45%

Traditional ROI: 4.79%

449 SPRINGWOOD COURT

Longwood, FL

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

$325,000

Airbnb cash on cash: 5.83%

Traditional cash on cash: 3.67%

Airbnb Rental Income: $3221

Traditional Rental Income: $1834

Airbnb ROI: 5.83%

Traditional ROI: 3.67%

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%