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
12 HORSEMAN COVE Longwood, FL Average monthly electric bill is $35.00 Welcome to this incredible opportunity in the ...	4 beds \| 2 baths \| 2,265 sq.ft.	$499,999	Airbnb cash on cash: 7.26% Traditional cash on cash: 4.5% Airbnb Rental Income: $5377 Traditional Rental Income: $3005 Airbnb ROI: 7.26% Traditional ROI: 4.5%
204 BROM BONES LANE Longwood, FL Under contract-accepting backup offers. Charming Pool Home with Expansive Outdoor Living l...	4 beds \| 3 baths \| 2,394 sq.ft.	$550,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 4.34% Airbnb Rental Income: $5377 Traditional Rental Income: $3419 Airbnb ROI: 6.04% Traditional ROI: 4.34%
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.	$195,000	Airbnb cash on cash: 7.4% Traditional cash on cash: 5.16% Airbnb Rental Income: $3221 Traditional Rental Income: $2080 Airbnb ROI: 7.4% Traditional ROI: 5.16%
641 E CHURCH AVENUE Longwood, FL Ready to save money on gas, your utility bills and home maintenance ? Welcome home to 641 ...	3 beds \| 2 baths \| 1,537 sq.ft.	$359,900	Airbnb cash on cash: 5.68% Traditional cash on cash: 4.96% Airbnb Rental Income: $3221 Traditional Rental Income: $2253 Airbnb ROI: 5.68% Traditional ROI: 4.96%
2681 AZALEA DRIVE Longwood, FL Crisp evenings, glowing firelight, and the perfect place to call home. This 3-bedroom, 2-b...	3 beds \| 2 baths \| 1,399 sq.ft.	$370,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 3.42% Airbnb Rental Income: $3221 Traditional Rental Income: $1994 Airbnb ROI: 4.87% Traditional ROI: 3.42%
1800 W LAKE BRANTLEY ROAD Longwood, FL Under contract-accepting backup offers. Charming Longwood Home in the Lake Brantley School...	3 beds \| 2 baths \| 1,486 sq.ft.	$384,900	Airbnb cash on cash: 4.85% Traditional cash on cash: 4.35% Airbnb Rental Income: $3221 Traditional Rental Income: $2313 Airbnb ROI: 4.85% Traditional ROI: 4.35%
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.	$375,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 4.19% Airbnb Rental Income: $3221 Traditional Rental Income: $2122 Airbnb ROI: 5.25% Traditional ROI: 4.19%
400 BRASSIE DRIVE Longwood, FL Under contract-accepting backup offers. Welcome to 400 Brassie Drive! This custom-built m...	4 beds \| 4 baths \| 4,003 sq.ft.	$889,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 1.71% Airbnb Rental Income: $5377 Traditional Rental Income: $3128 Airbnb ROI: 3.12% Traditional ROI: 1.71%
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.	$365,000	Airbnb cash on cash: 5.1% Traditional cash on cash: 3.17% Airbnb Rental Income: $3221 Traditional Rental Income: $1834 Airbnb ROI: 5.1% Traditional ROI: 3.17%
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.	$350,000	Airbnb cash on cash: 5.33% Traditional cash on cash: 3.56% Airbnb Rental Income: $3221 Traditional Rental Income: $1912 Airbnb ROI: 5.33% Traditional ROI: 3.56%
358 WINCHESTER COURT Longwood, FL $5000 lender credit with seller's preferred lender Renovated 3-bedroom, 2.5-bath townh...	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.	$450,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 2.99% Airbnb Rental Income: $3221 Traditional Rental Income: $2199 Airbnb ROI: 3.69% Traditional ROI: 2.99%
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.	$639,900	Airbnb cash on cash: 4.84% Traditional cash on cash: 2.39% Airbnb Rental Income: $5377 Traditional Rental Income: $2824 Airbnb ROI: 4.84% Traditional ROI: 2.39%
4 HUDSON COVE Longwood, FL Itâs your lucky day! Buyers financing fell through day before closing. Fully Renovat...	4 beds \| 3 baths \| 2,263 sq.ft.	$599,999	Airbnb cash on cash: 5.54% Traditional cash on cash: 2.66% Airbnb Rental Income: $5377 Traditional Rental Income: $2678 Airbnb ROI: 5.54% Traditional ROI: 2.66%
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%
223 ROYAL OAKS CIRCLE Longwood, FL BRING YOUR OFFER! MOTIVATED SELLERS will consider all offers! IMPROVED PRICE! One of the...	4 beds \| 2 baths \| 2,842 sq.ft.	$599,900	Airbnb cash on cash: 6.33% Traditional cash on cash: 3.51% Airbnb Rental Income: $5377 Traditional Rental Income: $2711 Airbnb ROI: 6.33% Traditional ROI: 3.51%
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.	$298,800	Airbnb cash on cash: 6.03% Traditional cash on cash: 4.17% Airbnb Rental Income: $3221 Traditional Rental Income: $1973 Airbnb ROI: 6.03% Traditional ROI: 4.17%
722 EAGLE AVENUE Longwood, FL Investor Goldmine in Longwood! Attention flippers, rehabbers, and savvy investors â This...	3 beds \| 2 baths \| 1,548 sq.ft.	$250,000	Airbnb cash on cash: 7.39% Traditional cash on cash: 5.94% Airbnb Rental Income: $3221 Traditional Rental Income: $2153 Airbnb ROI: 7.39% Traditional ROI: 5.94%
1821 STANLEY STREET Longwood, FL Seller will consider assisting buyer with closing cost and rate by down or other credits. ...	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%
1651 KENLYN DRIVE Longwood, FL This beautiful home is ready to be loved by new owners! Featuring 3 bedrooms, 2 bathrooms,...	3 beds \| 2 baths \| 1,687 sq.ft.	$375,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 3.58% Airbnb Rental Income: $3221 Traditional Rental Income: $2142 Airbnb ROI: 4.58% Traditional ROI: 3.58%
215 NOB HILL CIRCLE Longwood, FL Under contract-accepting backup offers. This is the one. Owner is looking for a CASH offer...	4 beds \| 3 baths \| 2,538 sq.ft.	$475,000	Airbnb cash on cash: 7.94% Traditional cash on cash: 6.11% Airbnb Rental Income: $5377 Traditional Rental Income: $3475 Airbnb ROI: 7.94% Traditional ROI: 6.11%
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.	$475,000	Airbnb cash on cash: 7.08% Traditional cash on cash: 4.14% Airbnb Rental Income: $5377 Traditional Rental Income: $2982 Airbnb ROI: 7.08% Traditional ROI: 4.14%
218 W MAGNOLIA AVENUE Longwood, FL Back on the market after 2025 TOTAL RENOVATION FULLY COMPLETED - Now this gorgeous propert...	3 beds \| 2 baths \| 1,574 sq.ft.	$386,900	Airbnb cash on cash: 4.6% Traditional cash on cash: 3.67% Airbnb Rental Income: $3221 Traditional Rental Income: $2157 Airbnb ROI: 4.6% Traditional ROI: 3.67%
154 SHADOW TRAIL Longwood, FL Under contract-accepting backup offers. Welcome to 154 Shadow Trail, a beautifully renovat...	3 beds \| 2 baths \| 1,417 sq.ft.	$439,900	Airbnb cash on cash: 3.74% Traditional cash on cash: 3.19% Airbnb Rental Income: $3221 Traditional Rental Income: $2270 Airbnb ROI: 3.74% Traditional ROI: 3.19%
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 \| 1,745 sq.ft.	$425,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 4.61% Airbnb Rental Income: $3221 Traditional Rental Income: $2491 Airbnb ROI: 4.62% Traditional ROI: 4.61%
821 SUTTER LOOP Longwood, FL NEW PRICE IMPROVEMENT SEPT 19!, NEW ROOF April 2025! 1 YEAR HOME WARRANTY! NO HOA FEE! ROO...	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%
1006 HANGING VINE POINT Longwood, FL ** Save Big: lender credit (based on loan amount) toward closing costs or rate buy-down wi...	4 beds \| 3 baths \| 2,540 sq.ft.	$649,900	Airbnb cash on cash: 5.25% Traditional cash on cash: 3.93% Airbnb Rental Income: $5377 Traditional Rental Income: $3488 Airbnb ROI: 5.25% Traditional ROI: 3.93%
335 RUTH BOULEVARD Longwood, FL Brand-New Custom Home in Prime Longwood Location-No HOA! This custom-build 4 bedroom ,3 ba...	4 beds \| 3 baths \| 2,014 sq.ft.	$560,000	Airbnb cash on cash: 6.86% Traditional cash on cash: 3.81% Airbnb Rental Income: $5377 Traditional Rental Income: $2698 Airbnb ROI: 6.86% Traditional ROI: 3.81%
209 SWEET GUM WAY Longwood, FL This updated 3-bedroom, 3-bathroom two-story townhome is tucked inside the highly desirabl...	3 beds \| 3 baths \| 1,746 sq.ft.	$460,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 2.62% Airbnb Rental Income: $3221 Traditional Rental Income: $2233 Airbnb ROI: 3.23% Traditional ROI: 2.62%
1204 DUNCAN COURT Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. VE...	4 beds \| 2 baths \| 2,292 sq.ft.	$519,900	Airbnb cash on cash: 6.37% Traditional cash on cash: 3.6% Airbnb Rental Income: $5377 Traditional Rental Income: $2947 Airbnb ROI: 6.37% Traditional ROI: 3.6%
287 HILLTOP DRIVE Longwood, FL Convenience, Land, Nature, Energy Efficiency. Keep a horse and chickens. It is rare to fin...	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%
526 SABAL TRAIL CIRCLE Longwood, FL Under contract-accepting backup offers. *Price Enhancement* MOTIVATED SELLER-- Come n...	4 beds \| 3 baths \| 2,609 sq.ft.	$575,000	Airbnb cash on cash: 5.81% Traditional cash on cash: 4.23% Airbnb Rental Income: $5377 Traditional Rental Income: $3441 Airbnb ROI: 5.81% Traditional ROI: 4.23%
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.	$419,900	Airbnb cash on cash: 4.9% Traditional cash on cash: 4.83% Airbnb Rental Income: $3221 Traditional Rental Income: $2465 Airbnb ROI: 4.9% Traditional ROI: 4.83%
1351 CANAL POINT ROAD Longwood, FL RECENT PRICE ADJUSTMENT *LAKESIDE LIVINGCOME SEE THIS Charming Traditional 4-Bedroom, ...	4 beds \| 3 baths \| 2,334 sq.ft.	$595,000	Airbnb cash on cash: 5.86% Traditional cash on cash: 3.62% Airbnb Rental Income: $5377 Traditional Rental Income: $3047 Airbnb ROI: 5.86% Traditional ROI: 3.62%

Vacation Rentals in Longwood

There are 77 vacation rental properties available for sale in the city of Longwood . The median list price of Airbnb properties available for sale in Longwood is $450,000 and the average price per square foot is $222. 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 77 Airbnb properties available for sale in Longwood.

In 2025, the best neighborhood to buy short term rental property is Longwood.

In October 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

12 HORSEMAN COVE

Longwood, FL

4 beds | 2 baths | 2,265 sq.ft.

$499,999

Airbnb cash on cash: 7.26%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $5377

Traditional Rental Income: $3005

Airbnb ROI: 7.26%

Traditional ROI: 4.5%

204 BROM BONES LANE

Longwood, FL

4 beds | 3 baths | 2,394 sq.ft.

$550,000

Airbnb cash on cash: 6.04%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $5377

Traditional Rental Income: $3419

Airbnb ROI: 6.04%

Traditional ROI: 4.34%

211 FAIRWAY DRIVE #211

Longwood, FL

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

$195,000

Airbnb cash on cash: 7.4%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $3221

Traditional Rental Income: $2080

Airbnb ROI: 7.4%

Traditional ROI: 5.16%

641 E CHURCH AVENUE

Longwood, FL

3 beds | 2 baths | 1,537 sq.ft.

$359,900

Airbnb cash on cash: 5.68%

Traditional cash on cash: 4.96%

Airbnb Rental Income: $3221

Traditional Rental Income: $2253

Airbnb ROI: 5.68%

Traditional ROI: 4.96%

2681 AZALEA DRIVE

Longwood, FL

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

$370,000

Airbnb cash on cash: 4.87%

Traditional cash on cash: 3.42%

Airbnb Rental Income: $3221

Traditional Rental Income: $1994

Airbnb ROI: 4.87%

Traditional ROI: 3.42%

1800 W LAKE BRANTLEY ROAD

Longwood, FL

3 beds | 2 baths | 1,486 sq.ft.

$384,900

Airbnb cash on cash: 4.85%

Traditional cash on cash: 4.35%

Airbnb Rental Income: $3221

Traditional Rental Income: $2313

Airbnb ROI: 4.85%

Traditional ROI: 4.35%

364 HOWARD BOULEVARD

Longwood, FL

3 beds | 2 baths | 1,400 sq.ft.

$375,000

Airbnb cash on cash: 5.25%

Traditional cash on cash: 4.19%

Airbnb Rental Income: $3221

Traditional Rental Income: $2122

Airbnb ROI: 5.25%

Traditional ROI: 4.19%

400 BRASSIE DRIVE

Longwood, FL

4 beds | 4 baths | 4,003 sq.ft.

$889,000

Airbnb cash on cash: 3.12%

Traditional cash on cash: 1.71%

Airbnb Rental Income: $5377

Traditional Rental Income: $3128

Airbnb ROI: 3.12%