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
214 SHERIDAN AVENUE Longwood, FL MULTIPLE OFFERS BEST AND FINAL DUE ON 4/25 BY 5:00PM Welcome to your next homeâw...	3 beds \| 2 baths \| 1,707 sq.ft.	$425,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 3.41% Airbnb Rental Income: $3221 Traditional Rental Income: $2306 Airbnb ROI: 3.88% Traditional ROI: 3.41%
420 W WEKIVA TRAIL Longwood, FL Under contract-accepting backup offers. A RARE opportunity in Wekiva awaits! Every major u...	3 beds \| 2 baths \| 1,787 sq.ft.	$448,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 3.16% Airbnb Rental Income: $3221 Traditional Rental Income: $2251 Airbnb ROI: 3.74% Traditional ROI: 3.16%
102 N SILVER CLUSTER COURT Longwood, FL Welcome to 102 Silver Cluster Ct N in Longwood, a beautifully maintained pool home under $...	3 beds \| 2 baths \| 1,166 sq.ft.	$395,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 3.07% Airbnb Rental Income: $3221 Traditional Rental Income: $1980 Airbnb ROI: 4.46% Traditional ROI: 3.07%
413 WILLOWBROOK LANE Longwood, FL One or more photo(s) has been virtually staged. Located in the highly sought-after Sabal P...	4 beds \| 2 baths \| 2,211 sq.ft.	$564,999	Airbnb cash on cash: 6.13% Traditional cash on cash: 4.96% Airbnb Rental Income: $5377 Traditional Rental Income: $3678 Airbnb ROI: 6.13% Traditional ROI: 4.96%
478 SABAL TRAIL CIRCLE Longwood, FL Welcome to the desirable Sabal Point community! Located at 478 Sabal Trail Circle in Longw...	4 beds \| 3 baths \| 2,529 sq.ft.	$645,000	Airbnb cash on cash: 4.8% Traditional cash on cash: 3.49% Airbnb Rental Income: $5377 Traditional Rental Income: $3502 Airbnb ROI: 4.8% Traditional ROI: 3.49%
308 SMOKERISE BOULEVARD Longwood, FL Welcome to 308 Smokerise Blvd., tucked away on a quiet corner lot within a cul-de-sac in t...	4 beds \| 2 baths \| 2,352 sq.ft.	$635,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 3.46% Airbnb Rental Income: $5377 Traditional Rental Income: $3370 Airbnb ROI: 5.01% Traditional ROI: 3.46%
257 GARY BOULEVARD Longwood, FL Under contract-accepting backup offers. Three bedrooms, two baths, a pool, and no HOA in o...	3 beds \| 2 baths \| 1,267 sq.ft.	$375,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 4.06% Airbnb Rental Income: $3221 Traditional Rental Income: $2151 Airbnb ROI: 5.04% Traditional ROI: 4.06%
451 STANTON PLACE Longwood, FL Welcome to Governorâs Point, a highly sought-after community in Wekiva, located in Longw...	3 beds \| 3 baths \| 1,682 sq.ft.	$334,900	Airbnb cash on cash: 3.82% Traditional cash on cash: 2.74% Airbnb Rental Income: $3221 Traditional Rental Income: $2154 Airbnb ROI: 3.82% Traditional ROI: 2.74%
860 Charlotte St. Longwood, FL 4-Bed / 3.5-Bath Home Built in 2006. -needs updating, new ac.	4 beds \| 4 baths \| N/A	$449,000	Airbnb cash on cash: 7.55% Traditional cash on cash: 5.25% Airbnb Rental Income: $5377 Traditional Rental Income: $3324 Airbnb ROI: 7.55% Traditional ROI: 5.25%
1889 RANCHLAND TRAIL Longwood, FL Welcome to this beautifully renovated 4-bedroom, 3-bathroom pool home, perfectly situated ...	4 beds \| 3 baths \| 2,333 sq.ft.	$998,900	Airbnb cash on cash: 2.92% Traditional cash on cash: 2.18% Airbnb Rental Income: $5377 Traditional Rental Income: $3601 Airbnb ROI: 2.92% Traditional ROI: 2.18%
1446 Vivaldi Pl Longwood, FL SEE VIRTUAL WALK-THRU VIDEO...Gated Bella Vista elegant & move in perfect 4 bdr 3 ba Pool ...	4 beds \| 3 baths \| 3,310 sq.ft.	$825,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 3.22% Airbnb Rental Income: $5377 Traditional Rental Income: $3949 Airbnb ROI: 3.67% Traditional ROI: 3.22%
470 FREEMAN STREET Longwood, FL Set on an oversized lot with Water VIEWS in the desirable Longwood Plantation community, 4...	4 beds \| 2 baths \| 2,261 sq.ft.	$490,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 4.57% Airbnb Rental Income: $5377 Traditional Rental Income: $3094 Airbnb ROI: 7.19% Traditional ROI: 4.57%
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: 3.79% Airbnb Rental Income: $5377 Traditional Rental Income: $3121 Airbnb ROI: 6.54% Traditional ROI: 3.79%
284 ISLAND SOUND COURT Longwood, FL Step into refined elegance and effortless sophistication in this nearly new Dockside maste...	4 beds \| 3 baths \| 2,692 sq.ft.	$799,999	Airbnb cash on cash: 3.56% Traditional cash on cash: 1.67% Airbnb Rental Income: $5377 Traditional Rental Income: $2884 Airbnb ROI: 3.56% Traditional ROI: 1.67%
1510 PELICAN STREET Longwood, FL Under contract-accepting backup offers. Completely Remodeled Home in Prime Location -NO HO...	3 beds \| 2 baths \| 1,269 sq.ft.	$349,999	Airbnb cash on cash: 5.02% Traditional cash on cash: 3.43% Airbnb Rental Income: $3221 Traditional Rental Income: $1973 Airbnb ROI: 5.02% Traditional ROI: 3.43%
410 GEORGIA AVENUE Longwood, FL Under contract-accepting backup offers. This fully renovated home blends style and functio...	3 beds \| 2 baths \| 1,588 sq.ft.	$435,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 3.06% Airbnb Rental Income: $3221 Traditional Rental Income: $2160 Airbnb ROI: 3.88% Traditional ROI: 3.06%
450 LONGMEADOW LANE Longwood, FL Excellent opportunity in Sabal Point. POOL house with two NEW HVACs. 4 bedrooms, 3.5 bathr...	4 beds \| 4 baths \| 2,623 sq.ft.	$539,000	Airbnb cash on cash: 6.54% Traditional cash on cash: 5.71% Airbnb Rental Income: $5377 Traditional Rental Income: $3873 Airbnb ROI: 6.54% Traditional ROI: 5.71%
351 W HORNBEAM DRIVE Longwood, FL Under contract-accepting backup offers. Under Construction. Welcome to one of the most exc...	4 beds \| 3 baths \| 2,778 sq.ft.	$750,000	Airbnb cash on cash: 4.59% Traditional cash on cash: -0.34% Airbnb Rental Income: $5377 Traditional Rental Income: $850 Airbnb ROI: 4.59% Traditional ROI: -0.34%
112 DES PINAR LANE Longwood, FL Under contract-accepting backup offers. Fully Remodeled Luxury Pool Home \| No HOA \| Priced...	4 beds \| 2 baths \| 1,604 sq.ft.	$419,000	Airbnb cash on cash: 8.65% Traditional cash on cash: 4.25% Airbnb Rental Income: $5377 Traditional Rental Income: $2566 Airbnb ROI: 8.65% Traditional ROI: 4.25%
307 COBLE DRIVE Longwood, FL Some homes just feel right the moment you walk inâ¦ and 307 Coble Drive is one of them. ...	4 beds \| 2 baths \| 1,987 sq.ft.	$475,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 4.8% Airbnb Rental Income: $5377 Traditional Rental Income: $3230 Airbnb ROI: 7.19% Traditional ROI: 4.8%
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.	$335,000	Airbnb cash on cash: 5.43% Traditional cash on cash: 5.14% Airbnb Rental Income: $3221 Traditional Rental Income: $2403 Airbnb ROI: 5.43% Traditional ROI: 5.14%
495 HOWARD AVENUE Longwood, FL Back on market! Welcome home! This stunning 4-bedroom, 2-bathroom residence has been compl...	4 beds \| 2 baths \| 1,855 sq.ft.	$419,999	Airbnb cash on cash: 9.09% Traditional cash on cash: 4.61% Airbnb Rental Income: $5377 Traditional Rental Income: $2527 Airbnb ROI: 9.09% Traditional ROI: 4.61%
700 LAKESIDE PLACE Longwood, FL Under contract-accepting backup offers. Beautifully renovated home in the heart of Longwoo...	3 beds \| 2 baths \| 1,279 sq.ft.	$375,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 3.97% Airbnb Rental Income: $3221 Traditional Rental Income: $2407 Airbnb ROI: 4.22% Traditional ROI: 3.97%
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: 3.11% Airbnb Rental Income: $5377 Traditional Rental Income: $3606 Airbnb ROI: 4.03% Traditional ROI: 3.11%
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%
1841 NORTH STREET Longwood, FL Super cute 3/2 single family home, 2 minutes to the Altamonte Mall, across the street from...	3 beds \| 2 baths \| 1,025 sq.ft.	$295,000	Airbnb cash on cash: 6.76% Traditional cash on cash: 5.54% Airbnb Rental Income: $3221 Traditional Rental Income: $2155 Airbnb ROI: 6.76% Traditional ROI: 5.54%
1209 ROXBORO ROAD Longwood, FL Fully Renovated Knollwood Estate \| Over $315K in Upgrades \| 0.70 Acre Lot Welcome to Ro...	4 beds \| 3 baths \| 3,332 sq.ft.	$799,999	Airbnb cash on cash: 4.07% Traditional cash on cash: 3.04% Airbnb Rental Income: $5377 Traditional Rental Income: $3522 Airbnb ROI: 4.07% Traditional ROI: 3.04%
1198 Bella Vista Cir Longwood, FL 1198 Bella Vista Cir, Longwood, FL 32779 \| Other	N/A beds \| N/A baths \| N/A	$319,990	Airbnb cash on cash: 2.41% Traditional cash on cash: 1.49% Airbnb Rental Income: $2039 Traditional Rental Income: $1232 Airbnb ROI: 2.41% Traditional ROI: 1.49%
1000 CROOKED OAK COURT Longwood, FL One or more photo(s) has been virtually staged. Sweetwater Oaks!! Outstanding 4BD 3 FULL B...	4 beds \| 3 baths \| 2,808 sq.ft.	$599,900	Airbnb cash on cash: 5.3% Traditional cash on cash: 4.82% Airbnb Rental Income: $5377 Traditional Rental Income: $4023 Airbnb ROI: 5.3% Traditional ROI: 4.82%
1508 MEADOWLARK STREET Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	3 beds \| 2 baths \| 1,308 sq.ft.	$360,000	Airbnb cash on cash: 5.08% Traditional cash on cash: 4.63% Airbnb Rental Income: $3221 Traditional Rental Income: $2344 Airbnb ROI: 5.08% Traditional ROI: 4.63%
3322 CANYON GRAND POINT Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Pi...	4 beds \| 3 baths \| 2,707 sq.ft.	$725,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 2.44% Airbnb Rental Income: $5377 Traditional Rental Income: $3402 Airbnb ROI: 3.76% Traditional ROI: 2.44%
289 WILMA STREET Longwood, FL Located in the heart of Historic Longwood, partially remodeled.	3 beds \| 2 baths \| 1,277 sq.ft.	$355,000	Airbnb cash on cash: 5.1% Traditional cash on cash: 4.38% Airbnb Rental Income: $3221 Traditional Rental Income: $2253 Airbnb ROI: 5.1% Traditional ROI: 4.38%
302 NEEDLES TRAIL Longwood, FL Under contract-accepting backup offers. Welcome to your private pool retreat in Wekiva Clu...	4 beds \| 2 baths \| 2,147 sq.ft.	$499,000	Airbnb cash on cash: 7.42% Traditional cash on cash: 5.28% Airbnb Rental Income: $5377 Traditional Rental Income: $3294 Airbnb ROI: 7.42% Traditional ROI: 5.28%
300 E SWEETWATER CREEK DRIVE Longwood, FL Fully RENOVATED 4 bdm/3 bath home !!! New Roof, New AC, New Kitchen, New Bathrooms, New Fl...	4 beds \| 3 baths \| 2,074 sq.ft.	$559,000	Airbnb cash on cash: 6.45% Traditional cash on cash: 4.24% Airbnb Rental Income: $5377 Traditional Rental Income: $3134 Airbnb ROI: 6.45% Traditional ROI: 4.24%
216 THISTLEWOOD CIRCLE Longwood, FL Nestled within the coveted community of Sweetwater Oaks, this exceptional lake-access resi...	4 beds \| 3 baths \| 2,272 sq.ft.	$639,900	Airbnb cash on cash: 4.93% Traditional cash on cash: 3.98% Airbnb Rental Income: $5377 Traditional Rental Income: $3722 Airbnb ROI: 4.93% Traditional ROI: 3.98%
601 FOX VALLEY DRIVE Longwood, FL Under contract-accepting backup offers. Welcome to 601 Fox Valley Drive & & PLEASE VIEW TH...	4 beds \| 2 baths \| 2,113 sq.ft.	$554,800	Airbnb cash on cash: 6.56% Traditional cash on cash: 4.59% Airbnb Rental Income: $5377 Traditional Rental Income: $3270 Airbnb ROI: 6.56% Traditional ROI: 4.59%
111 DELLWOOD DRIVE Longwood, FL Under contract-accepting backup offers. Beautifully updated Longwood home with a brand new...	4 beds \| 2 baths \| 2,126 sq.ft.	$490,000	Airbnb cash on cash: 7.37% Traditional cash on cash: 5.35% Airbnb Rental Income: $5377 Traditional Rental Income: $3364 Airbnb ROI: 7.37% Traditional ROI: 5.35%
739 RIVERBEND BOULEVARD Longwood, FL Welcome to 739 Riverbend Blvd, a rare Sweetwater Oaks offering where space, setting, and l...	4 beds \| 2 baths \| 2,382 sq.ft.	$625,000	Airbnb cash on cash: 5.6% Traditional cash on cash: 3.8% Airbnb Rental Income: $5377 Traditional Rental Income: $3241 Airbnb ROI: 5.6% Traditional ROI: 3.8%
1707 GRANGE CIRCLE Longwood, FL Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, ...	4 beds \| 2 baths \| 1,981 sq.ft.	$476,000	Airbnb cash on cash: 7.95% Traditional cash on cash: 5.75% Airbnb Rental Income: $5377 Traditional Rental Income: $3311 Airbnb ROI: 7.95% Traditional ROI: 5.75%
936 CITRUS WOOD COURT Longwood, FL Welcome to this beautifully updated 4-bedroom, 2-bath pool home tucked away on a quiet cul...	4 beds \| 2 baths \| 1,833 sq.ft.	$484,900	Airbnb cash on cash: 7.18% Traditional cash on cash: 4.72% Airbnb Rental Income: $5377 Traditional Rental Income: $3177 Airbnb ROI: 7.18% Traditional ROI: 4.72%

Vacation Rentals in Longwood

There are 61 vacation rental properties available for sale in the city of Longwood . The median list price of Airbnb properties available for sale in Longwood is $439,900 and the average price per square foot is $208. 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 61 Airbnb properties available for sale in Longwood.

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

In May 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

214 SHERIDAN AVENUE

Longwood, FL

3 beds | 2 baths | 1,707 sq.ft.

$425,000

Airbnb cash on cash: 3.88%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $3221

Traditional Rental Income: $2306

Airbnb ROI: 3.88%

Traditional ROI: 3.41%

420 W WEKIVA TRAIL

Longwood, FL

3 beds | 2 baths | 1,787 sq.ft.

$448,000

Airbnb cash on cash: 3.74%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $3221

Traditional Rental Income: $2251

Airbnb ROI: 3.74%

Traditional ROI: 3.16%

102 N SILVER CLUSTER COURT

Longwood, FL

3 beds | 2 baths | 1,166 sq.ft.

$395,000

Airbnb cash on cash: 4.46%

Traditional cash on cash: 3.07%

Airbnb Rental Income: $3221

Traditional Rental Income: $1980

Airbnb ROI: 4.46%

Traditional ROI: 3.07%

413 WILLOWBROOK LANE

Longwood, FL

4 beds | 2 baths | 2,211 sq.ft.

$564,999

Airbnb cash on cash: 6.13%

Traditional cash on cash: 4.96%

Airbnb Rental Income: $5377

Traditional Rental Income: $3678

Airbnb ROI: 6.13%

Traditional ROI: 4.96%

478 SABAL TRAIL CIRCLE

Longwood, FL

4 beds | 3 baths | 2,529 sq.ft.

$645,000

Airbnb cash on cash: 4.8%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $5377

Traditional Rental Income: $3502

Airbnb ROI: 4.8%

Traditional ROI: 3.49%

308 SMOKERISE BOULEVARD

Longwood, FL

4 beds | 2 baths | 2,352 sq.ft.

$635,000

Airbnb cash on cash: 5.01%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $5377

Traditional Rental Income: $3370

Airbnb ROI: 5.01%

Traditional ROI: 3.46%

257 GARY BOULEVARD

Longwood, FL

3 beds | 2 baths | 1,267 sq.ft.

$375,000

Airbnb cash on cash: 5.04%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $3221

Traditional Rental Income: $2151

Airbnb ROI: 5.04%

Traditional ROI: 4.06%

451 STANTON PLACE

Longwood, FL

3 beds | 3 baths | 1,682 sq.ft.

$334,900

Airbnb cash on cash: 3.82%

Traditional cash on cash: 2.74%

Airbnb Rental Income: $3221

Traditional Rental Income: $2154

Airbnb ROI: 3.82%