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.	$449,000	Airbnb cash on cash: 6.48% Traditional cash on cash: 4.89% Airbnb Rental Income: $4558 Traditional Rental Income: $2944 Airbnb ROI: 6.48% Traditional ROI: 4.89%
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%
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%
128 CAMPHOR CIRCLE #C Oldsmar, FL Under contract-accepting backup offers. Welcome home to this beautifully updated 2-bedroom...	2 beds \| 2 baths \| 915 sq.ft.	$154,900	Airbnb cash on cash: 9.16% Traditional cash on cash: 8.82% Airbnb Rental Income: $2403 Traditional Rental Income: $1763 Airbnb ROI: 9.16% Traditional ROI: 8.82%
646 TIMBER BAY CIRCLE W Oldsmar, FL LOCATION - LOCATION - LOCATION - LOVE WHERE YOU LIVE - ONE STORY POOL HOME - PRICED TO SEL...	3 beds \| 2 baths \| 1,554 sq.ft.	$419,000	Airbnb cash on cash: 4.27% Traditional cash on cash: 4.24% Airbnb Rental Income: $3329 Traditional Rental Income: $2570 Airbnb ROI: 4.27% Traditional ROI: 4.24%
421 SHORE DRIVE E Oldsmar, FL Under contract-accepting backup offers. Prime investment opportunity in one of Oldsmarâs...	3 beds \| 2 baths \| 1,416 sq.ft.	$285,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 6.41% Airbnb Rental Income: $3329 Traditional Rental Income: $2438 Airbnb ROI: 6.96% Traditional ROI: 6.41%
150 POOLE PLACE Oldsmar, FL From the moment you arrive at this East Lake Woodlands villa, it feels like youâve stepp...	4 beds \| 2 baths \| 1,550 sq.ft.	$337,500	Airbnb cash on cash: 8.13% Traditional cash on cash: 4.12% Airbnb Rental Income: $4558 Traditional Rental Income: $2340 Airbnb ROI: 8.13% Traditional ROI: 4.12%
350 HOLLY HILL ROAD Oldsmar, FL Under contract-accepting backup offers. UNDER CONTRACT ACCEPTING BACK UP OFFERSWelcome t...	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%
316 LAFAYETTE BOULEVARD Oldsmar, FL Under contract-accepting backup offers. Live the ultimate Florida lifestyle in this specta...	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%
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%
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.	$1,500,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 0.35% Airbnb Rental Income: $4558 Traditional Rental Income: $3597 Airbnb ROI: 0.36% Traditional ROI: 0.35%
205 BENGAL CIRCLE Oldsmar, FL HIGH AND DRY! Elevation certificate available. Backing up to a nature preserve, this 4 bed...	4 beds \| 3 baths \| 2,733 sq.ft.	$819,900	Airbnb cash on cash: 2.58% Traditional cash on cash: 1.72% Airbnb Rental Income: $4558 Traditional Rental Income: $2950 Airbnb ROI: 2.58% Traditional ROI: 1.72%
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%
20 SYLVIA PLACE Oldsmar, FL One or more photo(s) has been virtually staged. # Price Drop. Perfect Timing. **The morni...	4 beds \| 2 baths \| 1,550 sq.ft.	$337,000	Airbnb cash on cash: 7.88% Traditional cash on cash: 5.29% Airbnb Rental Income: $4558 Traditional Rental Income: $2790 Airbnb ROI: 7.88% Traditional ROI: 5.29%
2159 WARWICK DRIVE Oldsmar, FL BACK ON MARKET- BUYER CANCELLED BEFORE INSPECTIONS. Settle in to your dream home in the c...	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%
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%
316 COUNTRY CLUB DRIVE Oldsmar, FL One or more photo(s) has been virtually staged. Step into this mid-century modern 3-bedroo...	3 beds \| 2 baths \| 1,344 sq.ft.	$369,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 5.34% Airbnb Rental Income: $3329 Traditional Rental Income: $2344 Airbnb ROI: 6.04% Traditional ROI: 5.34%
3087 DUANE AVENUE Oldsmar, FL HIGH AND DRY! THIS HOME NEVER FLOODED! Welcome to this charming, move-in-ready home offeri...	3 beds \| 2 baths \| 1,296 sq.ft.	$438,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 2.96% Airbnb Rental Income: $3329 Traditional Rental Income: $2103 Airbnb ROI: 4.14% Traditional ROI: 2.96%
145 BLUE MARLIN DRIVE Oldsmar, FL The Time is NOW to own your place in the Florida sun. This spacious, contemporary residen...	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.	$199,900	Airbnb cash on cash: 4% Traditional cash on cash: 3.96% Airbnb Rental Income: $2403 Traditional Rental Income: $1807 Airbnb ROI: 4% Traditional ROI: 3.96%
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.	$549,900	Airbnb cash on cash: 5.1% Traditional cash on cash: 3.74% Airbnb Rental Income: $4558 Traditional Rental Income: $2911 Airbnb ROI: 5.1% Traditional ROI: 3.74%
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 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.	$345,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 2.96% Airbnb Rental Income: $3329 Traditional Rental Income: $2217 Airbnb ROI: 4.09% Traditional ROI: 2.96%
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.	$164,000	Airbnb cash on cash: 8.18% Traditional cash on cash: 7.46% Airbnb Rental Income: $2403 Traditional Rental Income: $1700 Airbnb ROI: 8.18% Traditional ROI: 7.46%
315 SHORE DRIVE E Oldsmar, FL REDUCED! A View of the Picturesque view of Tampa Bay. This cozy 3 Bedroom home has double ...	3 beds \| 2 baths \| 1,477 sq.ft.	$274,900	Airbnb cash on cash: 8.34% Traditional cash on cash: 6.1% Airbnb Rental Income: $3329 Traditional Rental Income: $2006 Airbnb ROI: 8.34% Traditional ROI: 6.1%
934 LUCAS LANE Oldsmar, FL Location! Location! Lovely 3 bedroom 2 bath villa style single family home with atttached ...	3 beds \| 2 baths \| 1,610 sq.ft.	$425,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 2.83% Airbnb Rental Income: $3329 Traditional Rental Income: $2389 Airbnb ROI: 3.32% Traditional ROI: 2.83%
520 CANAL WAY Oldsmar, FL Under contract-accepting backup offers. Welcome to 520 Canal Way in Gull-Aire Village, a w...	3 beds \| 2 baths \| 1,473 sq.ft.	$314,900	Airbnb cash on cash: 6.92% Traditional cash on cash: 6.75% Airbnb Rental Income: $3329 Traditional Rental Income: $2535 Airbnb ROI: 6.92% Traditional ROI: 6.75%
311 VISTA CRUISER LANE Oldsmar, FL This stunning 3-bedroom, 2.5-bath townhome offers the perfect blend of style, comfort, and...	3 beds \| 3 baths \| 1,547 sq.ft.	$385,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 3.39% Airbnb Rental Income: $3329 Traditional Rental Income: $2284 Airbnb ROI: 4.22% Traditional ROI: 3.39%
214 CARYL WAY Oldsmar, FL One or more photo(s) has been virtually staged. Rare 3-bedroom opportunity! Located in th...	3 beds \| 2 baths \| 1,292 sq.ft.	$239,000	Airbnb cash on cash: 9.78% Traditional cash on cash: 7.57% Airbnb Rental Income: $3329 Traditional Rental Income: $2086 Airbnb ROI: 9.78% Traditional ROI: 7.57%
1814 DRIFTWOOD CIRCLE S Oldsmar, FL Under contract-accepting backup offers. A MUST SEE... this 4 bed/ 2bath/1 garage Home has ...	4 beds \| 2 baths \| 1,618 sq.ft.	$419,000	Airbnb cash on cash: 7.67% Traditional cash on cash: 4.75% Airbnb Rental Income: $4558 Traditional Rental Income: $2465 Airbnb ROI: 7.67% Traditional ROI: 4.75%
317 SHORE DRIVE E Oldsmar, FL Stunning Tampa Bay Views in Prime Oldsmar Location â Updated & Move-In Ready! Enjoy b...	3 beds \| 2 baths \| 1,660 sq.ft.	$494,900	Airbnb cash on cash: 3% Traditional cash on cash: 2.58% Airbnb Rental Income: $3329 Traditional Rental Income: $2391 Airbnb ROI: 3% Traditional ROI: 2.58%
105 PALMETTO COURT Oldsmar, FL Just what you have been waiting for....! FIRST floor, pet friendly (up to 40 pounds), cond...	2 beds \| 2 baths \| 1,054 sq.ft.	$179,000	Airbnb cash on cash: 7.69% Traditional cash on cash: 7.6% Airbnb Rental Income: $2403 Traditional Rental Income: $1798 Airbnb ROI: 7.69% Traditional ROI: 7.6%
313 CONGRESS STREET Oldsmar, FL Charming, Move-In Ready Home â Never Flooded, Beautifully Updated, and Priced to Sell! ...	3 beds \| 2 baths \| 1,133 sq.ft.	$349,900	Airbnb cash on cash: 6.35% Traditional cash on cash: 4.77% Airbnb Rental Income: $3329 Traditional Rental Income: $2065 Airbnb ROI: 6.35% Traditional ROI: 4.77%

Vacation Rentals in Oldsmar

There are 60 vacation rental properties available for sale in the city of Oldsmar . The median list price of Airbnb properties available for sale in Oldsmar is $399,450 and the average price per square foot is $215. 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 60 Airbnb properties available for sale in Oldsmar.

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

In November 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.

$449,000

Airbnb cash on cash: 6.48%

Traditional cash on cash: 4.89%

Airbnb Rental Income: $4558

Traditional Rental Income: $2944

Airbnb ROI: 6.48%

Traditional ROI: 4.89%

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%

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%

Traditional ROI: 7.5%

128 CAMPHOR CIRCLE #C

Oldsmar, FL

2 beds | 2 baths | 915 sq.ft.

$154,900

Airbnb cash on cash: 9.16%

Traditional cash on cash: 8.82%

Airbnb Rental Income: $2403

Traditional Rental Income: $1763

Airbnb ROI: 9.16%

Traditional ROI: 8.82%

646 TIMBER BAY CIRCLE W

Oldsmar, FL

3 beds | 2 baths | 1,554 sq.ft.

$419,000

Airbnb cash on cash: 4.27%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $3329

Traditional Rental Income: $2570

Airbnb ROI: 4.27%

Traditional ROI: 4.24%

421 SHORE DRIVE E

Oldsmar, FL

3 beds | 2 baths | 1,416 sq.ft.

$285,000

Airbnb cash on cash: 6.96%

Traditional cash on cash: 6.41%

Airbnb Rental Income: $3329

Traditional Rental Income: $2438

Airbnb ROI: 6.96%