Airbnb Properties for Sale in Oldsmar, FL

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

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

Airbnb For Sale in Oldsmar, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
505 OAKWOOD BOULEVARD Oldsmar, FL Welcome to this CHARMING HOME tucked away on a quiet, divided street in BEAUTIFUL DOWNTOWN...	4 beds \| 2 baths \| 1,993 sq.ft.	$465,000	Airbnb cash on cash: 6.22% Traditional cash on cash: 4.69% Airbnb Rental Income: $4558 Traditional Rental Income: $2944 Airbnb ROI: 6.22% Traditional ROI: 4.69%
502 TIMBER BAY CIRCLE E Oldsmar, FL Welcome to this stunningly spacious and well-maintained pool home nestled in one of the mo...	4 beds \| 2 baths \| 1,658 sq.ft.	$425,000	Airbnb cash on cash: 6.55% Traditional cash on cash: 3.9% Airbnb Rental Income: $4558 Traditional Rental Income: $2555 Airbnb ROI: 6.55% Traditional ROI: 3.9%
102 BRENT CIRCLE Oldsmar, FL Under contract-accepting backup offers. Huge Price Reduction immediate equity! Ready to m...	3 beds \| 3 baths \| 1,834 sq.ft.	$360,000	Airbnb cash on cash: 5.65% Traditional cash on cash: 5.45% Airbnb Rental Income: $3329 Traditional Rental Income: $2518 Airbnb ROI: 5.65% Traditional ROI: 5.45%
436 LAFAYETTE BOULEVARD Oldsmar, FL One or more photo(s) has been virtually staged. Must see this 4 bedroom/2.5 bath home with...	4 beds \| 3 baths \| 2,695 sq.ft.	$700,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 2.65% Airbnb Rental Income: $4558 Traditional Rental Income: $3466 Airbnb ROI: 2.87% Traditional ROI: 2.65%
200 GRETCHEN COURT Oldsmar, FL WELCOME HOME! Enjoy maintenance free Living in this Gated Community of Quail Forest which ...	3 beds \| 2 baths \| 1,445 sq.ft.	$374,900	Airbnb cash on cash: 4.03% Traditional cash on cash: 3.1% Airbnb Rental Income: $3329 Traditional Rental Income: $2258 Airbnb ROI: 4.03% Traditional ROI: 3.1%
382 ROSALIND LANE Oldsmar, FL Welcome to 382 Rosalind Ln., an extraordinary home in the exclusive gated community of Bay...	4 beds \| 3 baths \| 3,273 sq.ft.	$849,990	Airbnb cash on cash: 2.37% Traditional cash on cash: 1.2% Airbnb Rental Income: $4558 Traditional Rental Income: $2684 Airbnb ROI: 2.37% Traditional ROI: 1.2%
1909 CASTLE BAY COURT Oldsmar, FL --WONT LAST LONG---Discover this immaculate 3-bedroom, 2-bath home with garage located on ...	3 beds \| 2 baths \| 1,410 sq.ft.	$394,000	Airbnb cash on cash: 5.06% Traditional cash on cash: 4.3% Airbnb Rental Income: $3329 Traditional Rental Income: $2304 Airbnb ROI: 5.06% Traditional ROI: 4.3%
134 SYCAMORE LANE #H Oldsmar, FL This beautifully maintained 2 bedroom, 2 bath condo in fantastic Gardens of Forest lakes, ...	2 beds \| 2 baths \| 915 sq.ft.	$169,000	Airbnb cash on cash: 7.88% Traditional cash on cash: 7.5% Airbnb Rental Income: $2403 Traditional Rental Income: $1752 Airbnb ROI: 7.88% Traditional ROI: 7.5%
150 TADS TRAIL Oldsmar, FL VILLA with TRANQUIL GOLF COURSE VIEWS IN EAST LAKE WOODLANDS. This well Maintained VILLA...	3 beds \| 2 baths \| 1,695 sq.ft.	$379,500	Airbnb cash on cash: 3.32% Traditional cash on cash: 3.04% Airbnb Rental Income: $3329 Traditional Rental Income: $2485 Airbnb ROI: 3.32% Traditional ROI: 3.04%
646 TIMBER BAY CIRCLE W Oldsmar, FL LOVE WHERE YOU LIVE - ONE STORY POOL HOME! Welcome to this MOVE IN READY 3 bedroom, 2 remo...	3 beds \| 2 baths \| 1,554 sq.ft.	$429,000	Airbnb cash on cash: 4.15% Traditional cash on cash: 4.12% Airbnb Rental Income: $3329 Traditional Rental Income: $2570 Airbnb ROI: 4.15% Traditional ROI: 4.12%
150 POOLE PLACE Oldsmar, FL Welcome to this stunning, fully renovated 4 bedroom, 2 bathroom East Lake Woodlands villa!...	4 beds \| 2 baths \| 1,550 sq.ft.	$347,500	Airbnb cash on cash: 7.87% Traditional cash on cash: 3.98% Airbnb Rental Income: $4558 Traditional Rental Income: $2340 Airbnb ROI: 7.87% Traditional ROI: 3.98%
350 HOLLY HILL ROAD Oldsmar, FL Welcome to this inviting 4-bedroom, 2-bathroom home located in the highly sought-after Eas...	4 beds \| 2 baths \| 2,510 sq.ft.	$669,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 2.48% Airbnb Rental Income: $4558 Traditional Rental Income: $2931 Airbnb ROI: 3.56% Traditional ROI: 2.48%
30 TADS TRAIL Oldsmar, FL Move in ready corner unit villa in desirable Eastlake woodlands gated community. All the w...	3 beds \| 2 baths \| 1,450 sq.ft.	$410,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 2.69% Airbnb Rental Income: $3329 Traditional Rental Income: $2434 Airbnb ROI: 3.08% Traditional ROI: 2.69%
316 LAFAYETTE BOULEVARD Oldsmar, FL Live the ultimate Florida lifestyle in this spectacular Craftsman-style home in the heart ...	4 beds \| 4 baths \| 2,848 sq.ft.	$640,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 3.77% Airbnb Rental Income: $4558 Traditional Rental Income: $3604 Airbnb ROI: 3.78% Traditional ROI: 3.77%
906 VINEYARD LANE Oldsmar, FL One or more photo(s) has been virtually staged. Elegant 3-Bed, 2.5-Bath Townhome with 2.5%...	3 beds \| 3 baths \| 1,525 sq.ft.	$380,000	Airbnb cash on cash: 3.31% Traditional cash on cash: 2.41% Airbnb Rental Income: $3329 Traditional Rental Income: $2263 Airbnb ROI: 3.31% Traditional ROI: 2.41%
100 INGRID PLACE Oldsmar, FL Great opportunity to own this Lovely Updated 3 Bed, 2.5 Bath East Lake Woodlands Townhouse...	3 beds \| 3 baths \| 1,755 sq.ft.	$299,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 4.51% Airbnb Rental Income: $3329 Traditional Rental Income: $2484 Airbnb ROI: 4.87% Traditional ROI: 4.51%
10 ARBOR LANE Oldsmar, FL BRAND NEW AC / NEW ROOF 2022 / POOL RE-SURFACED 2018 / RARE TO MARKET GOLF COURSE FRONTAGE...	4 beds \| 2 baths \| 2,318 sq.ft.	$669,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 2.41% Airbnb Rental Income: $4558 Traditional Rental Income: $3177 Airbnb ROI: 3.11% Traditional ROI: 2.41%
106 CUTLASS WAY Oldsmar, FL Fully updated and move-in ready 3-bedroom, 2.5-bath townhome in highly desirable Hayes Par...	3 beds \| 3 baths \| 1,365 sq.ft.	$365,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 3.06% Airbnb Rental Income: $3329 Traditional Rental Income: $2156 Airbnb ROI: 4.31% Traditional ROI: 3.06%
347 COUNTRY CLUB DRIVE Oldsmar, FL "Move-In Ready"... Beautifully and Completely Refurbished Single Family Pool Home, (3) Bed...	3 beds \| 2 baths \| 1,280 sq.ft.	$449,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 4.23% Airbnb Rental Income: $3329 Traditional Rental Income: $2431 Airbnb ROI: 4.59% Traditional ROI: 4.23%
316 SHORE DRIVE E Oldsmar, FL Wake up to million-dollar views, and unwind with spectacular sunsets - this is the waterfr...	4 beds \| 3 baths \| 2,496 sq.ft.	$1,575,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 0.29% Airbnb Rental Income: $4558 Traditional Rental Income: $3597 Airbnb ROI: 0.29% Traditional ROI: 0.29%
204 SHORE DRIVE W Oldsmar, FL Prime Oldsmar Location! This 3-bedroom, 2-bath, 1-car garage home sits on a spacious quart...	3 beds \| 2 baths \| 1,374 sq.ft.	$380,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 4.08% Airbnb Rental Income: $3329 Traditional Rental Income: $2409 Airbnb ROI: 4.57% Traditional ROI: 4.08%
102 SHOREVIEW LANE Oldsmar, FL No water damage! High & Dry!!!Charming 3-Bedroom Home with Pool on Corner Lot! Welcome to ...	3 beds \| 2 baths \| 1,250 sq.ft.	$399,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 3.16% Airbnb Rental Income: $3329 Traditional Rental Income: $2057 Airbnb ROI: 4.57% Traditional ROI: 3.16%
429 EVERGREEN DRIVE Oldsmar, FL Under contract-accepting backup offers. High & Dry from the storms! Welcome to your dream ...	4 beds \| 2 baths \| 1,523 sq.ft.	$360,000	Airbnb cash on cash: 8.17% Traditional cash on cash: 5.92% Airbnb Rental Income: $4558 Traditional Rental Income: $2849 Airbnb ROI: 8.17% Traditional ROI: 5.92%
2159 WARWICK DRIVE Oldsmar, FL Settle in to your dream home in the coveted subdivision of Warwick Hills within Eastlake W...	4 beds \| 3 baths \| 2,673 sq.ft.	$835,000	Airbnb cash on cash: 2.6% Traditional cash on cash: 2.58% Airbnb Rental Income: $4558 Traditional Rental Income: $3592 Airbnb ROI: 2.6% Traditional ROI: 2.58%
143 LAKESIDE DRIVE #143 Oldsmar, FL ***NON FLOOD ZONE! Step into comfort and style with this beautifully updated 2-bedroom, 2-...	2 beds \| 2 baths \| 1,094 sq.ft.	$214,900	Airbnb cash on cash: 3.55% Traditional cash on cash: 3.54% Airbnb Rental Income: $2403 Traditional Rental Income: $1811 Airbnb ROI: 3.55% Traditional ROI: 3.54%
2101 SUNSET WIND LOOP Oldsmar, FL Welcome to 2101 Sunset Wind Loop â A Beautifully Maintained Townhome in the Heart of Old...	4 beds \| 3 baths \| 2,587 sq.ft.	$525,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.24% Airbnb Rental Income: $4558 Traditional Rental Income: $3170 Airbnb ROI: 4.13% Traditional ROI: 3.24%
215 WOODS LANDING TRAIL Oldsmar, FL Step into luxury with this beautifully upgraded home featuring designer finishes throughou...	3 beds \| 3 baths \| 1,450 sq.ft.	$349,900	Airbnb cash on cash: 4.28% Traditional cash on cash: 3% Airbnb Rental Income: $3329 Traditional Rental Income: $2167 Airbnb ROI: 4.28% Traditional ROI: 3%
211 ARLINGTON AVENUE E Oldsmar, FL One or more photo(s) has been virtually staged. Located in one of Oldsmar's most sought af...	4 beds \| 3 baths \| 1,954 sq.ft.	$535,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 4.05% Airbnb Rental Income: $4558 Traditional Rental Income: $2868 Airbnb ROI: 5.54% Traditional ROI: 4.05%
3087 DUANE AVENUE Oldsmar, FL One or more photo(s) has been virtually staged. Welcome to this charming three-bedroom, tw...	3 beds \| 2 baths \| 1,296 sq.ft.	$450,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 2.86% Airbnb Rental Income: $3329 Traditional Rental Income: $2103 Airbnb ROI: 4.01% Traditional ROI: 2.86%
145 BLUE MARLIN DRIVE Oldsmar, FL NEW GREAT PRICE! This spacious, contemporary residence offers the perfect blend of luxury...	3 beds \| 2 baths \| 1,504 sq.ft.	$249,900	Airbnb cash on cash: 8.74% Traditional cash on cash: 7.01% Airbnb Rental Income: $3329 Traditional Rental Income: $2177 Airbnb ROI: 8.74% Traditional ROI: 7.01%
204 MARY DRIVE Oldsmar, FL An absolute must see!! Beautifully maintained 2 bedroom, 2 bath condo nestled in sought af...	2 beds \| 2 baths \| 1,094 sq.ft.	$209,900	Airbnb cash on cash: 3.76% Traditional cash on cash: 3.73% Airbnb Rental Income: $2403 Traditional Rental Income: $1807 Airbnb ROI: 3.76% Traditional ROI: 3.73%
412 PINEWOOD DRIVE Oldsmar, FL Welcome to this exquisite Florida home where tranquility meets modern comfort. Positioned ...	4 beds \| 2 baths \| 2,430 sq.ft.	$569,900	Airbnb cash on cash: 4.88% Traditional cash on cash: 3.57% Airbnb Rental Income: $4558 Traditional Rental Income: $2911 Airbnb ROI: 4.88% Traditional ROI: 3.57%
113 NINA WAY #113 Oldsmar, FL Here is your opportunity to purchase a great condo in the popular East lake Woodlands deve...	2 beds \| 2 baths \| 1,094 sq.ft.	$225,000	Airbnb cash on cash: 5.81% Traditional cash on cash: 5.79% Airbnb Rental Income: $2403 Traditional Rental Income: $1810 Airbnb ROI: 5.81% Traditional ROI: 5.79%
337 WOODLAKE WYNDE Oldsmar, FL First floor end unit condo located in the Woodlake Run area of gated East Lake Woodlands C...	2 beds \| 2 baths \| 924 sq.ft.	$160,000	Airbnb cash on cash: 8.37% Traditional cash on cash: 7.86% Airbnb Rental Income: $2403 Traditional Rental Income: $1736 Airbnb ROI: 8.37% Traditional ROI: 7.86%
403 SAINT PETERSBURG DRIVE W Oldsmar, FL LOCATION LOCATION LOCATION----OWNER SAYS !NEW ROOF POSSIBLE AT CLOSING---- 3 BED 2 BATH. H...	3 beds \| 2 baths \| 1,458 sq.ft.	$399,900	Airbnb cash on cash: 5.34% Traditional cash on cash: 4.48% Airbnb Rental Income: $3329 Traditional Rental Income: $2264 Airbnb ROI: 5.34% Traditional ROI: 4.48%
235 WOODRIDGE CIRCLE Oldsmar, FL Owner reduced for fast sale. Bring offers. Don't pass this up. Reduced for fast sale. B...	3 beds \| 2 baths \| 1,666 sq.ft.	$425,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 1.13% Airbnb Rental Income: $3329 Traditional Rental Income: $2440 Airbnb ROI: 1.5% Traditional ROI: 1.13%
403 E TUSCAN LANE E Oldsmar, FL Welcome home in Oldsmar, FL! This two-story 1,525 square foot townhouse, located in the HI...	3 beds \| 3 baths \| 1,525 sq.ft.	$350,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 2.9% Airbnb Rental Income: $3329 Traditional Rental Income: $2217 Airbnb ROI: 4.02% Traditional ROI: 2.9%
819 SATINLEAF AVENUE Oldsmar, FL MOVE-IN-READY-Oldsmar home (Manors of Forest Lakes Phase 2 is a split bedroom 3 bedroom 2 ...	3 beds \| 2 baths \| 1,688 sq.ft.	$565,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 2.57% Airbnb Rental Income: $3329 Traditional Rental Income: $2425 Airbnb ROI: 2.87% Traditional ROI: 2.57%
106 MEADOW LANE #106 Oldsmar, FL PRICE REDUCED~~Motivated Seller~~2/2 in highly desired Eastlake Woodlands, The Meadows~~th...	2 beds \| 2 baths \| 879 sq.ft.	$174,900	Airbnb cash on cash: 7.63% Traditional cash on cash: 6.94% Airbnb Rental Income: $2403 Traditional Rental Income: $1700 Airbnb ROI: 7.63% Traditional ROI: 6.94%
315 SHORE DRIVE E Oldsmar, FL Cozy 3 Bedroom home sits across from the Picturesque view of Tampa Bay. This home has dou...	3 beds \| 2 baths \| 1,477 sq.ft.	$329,999	Airbnb cash on cash: 6.8% Traditional cash on cash: 4.94% Airbnb Rental Income: $3329 Traditional Rental Income: $2006 Airbnb ROI: 6.8% Traditional ROI: 4.94%

Vacation Rentals in Oldsmar

There are 65 vacation rental properties available for sale in the city of Oldsmar . The median list price of Airbnb properties available for sale in Oldsmar is $399,950 and the average price per square foot is $216. The cash on cash return on vacation rentals in Oldsmar is 4.00%. The average monthly short term rental income in Oldsmar is $3,329.

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

There are 65 Airbnb properties available for sale in Oldsmar.

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

In October 2025, the average Airbnb occupancy rate in Oldsmar is 58%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Oldsmar, FL

505 OAKWOOD BOULEVARD

Oldsmar, FL

4 beds | 2 baths | 1,993 sq.ft.

$465,000

Airbnb cash on cash: 6.22%

Traditional cash on cash: 4.69%

Airbnb Rental Income: $4558

Traditional Rental Income: $2944

Airbnb ROI: 6.22%

Traditional ROI: 4.69%

502 TIMBER BAY CIRCLE E

Oldsmar, FL

4 beds | 2 baths | 1,658 sq.ft.

$425,000

Airbnb cash on cash: 6.55%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $4558

Traditional Rental Income: $2555

Airbnb ROI: 6.55%

Traditional ROI: 3.9%

102 BRENT CIRCLE

Oldsmar, FL

3 beds | 3 baths | 1,834 sq.ft.

$360,000

Airbnb cash on cash: 5.65%

Traditional cash on cash: 5.45%

Airbnb Rental Income: $3329

Traditional Rental Income: $2518

Airbnb ROI: 5.65%

Traditional ROI: 5.45%

436 LAFAYETTE BOULEVARD

Oldsmar, FL

4 beds | 3 baths | 2,695 sq.ft.

$700,000

Airbnb cash on cash: 2.87%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $4558

Traditional Rental Income: $3466

Airbnb ROI: 2.87%

Traditional ROI: 2.65%

200 GRETCHEN COURT

Oldsmar, FL

3 beds | 2 baths | 1,445 sq.ft.

$374,900

Airbnb cash on cash: 4.03%

Traditional cash on cash: 3.1%

Airbnb Rental Income: $3329

Traditional Rental Income: $2258

Airbnb ROI: 4.03%

Traditional ROI: 3.1%

382 ROSALIND LANE

Oldsmar, FL

4 beds | 3 baths | 3,273 sq.ft.

$849,990

Airbnb cash on cash: 2.37%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $4558

Traditional Rental Income: $2684

Airbnb ROI: 2.37%

Traditional ROI: 1.2%

1909 CASTLE BAY COURT

Oldsmar, FL

3 beds | 2 baths | 1,410 sq.ft.

$394,000

Airbnb cash on cash: 5.06%

Traditional cash on cash: 4.3%

Airbnb Rental Income: $3329

Traditional Rental Income: $2304

Airbnb ROI: 5.06%

Traditional ROI: 4.3%

134 SYCAMORE LANE #H

Oldsmar, FL

2 beds | 2 baths | 915 sq.ft.

$169,000

Airbnb cash on cash: 7.88%

Traditional cash on cash: 7.5%

Airbnb Rental Income: $2403

Traditional Rental Income: $1752

Airbnb ROI: 7.88%