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
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.	$448,000	Airbnb cash on cash: 6.17% Traditional cash on cash: 3.65% Airbnb Rental Income: $4558 Traditional Rental Income: $2555 Airbnb ROI: 6.17% Traditional ROI: 3.65%
102 BRENT CIRCLE Oldsmar, FL Huge Price Reduction immediate equity! Ready to move into. Seller Says Sell! Seller is Re...	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%
632 LAKE CYPRESS CIRCLE Oldsmar, FL Under contract-accepting backup offers. Reduced. Florida Pool Home! Welcome to your brigh...	4 beds \| 2 baths \| 1,906 sq.ft.	$563,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 3.33% Airbnb Rental Income: $4558 Traditional Rental Income: $2911 Airbnb ROI: 4.66% Traditional ROI: 3.33%
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.	$800,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 2.2% Airbnb Rental Income: $4558 Traditional Rental Income: $3466 Airbnb ROI: 2.39% Traditional ROI: 2.2%
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.	$852,990	Airbnb cash on cash: 2.35% Traditional cash on cash: 1.19% Airbnb Rental Income: $4558 Traditional Rental Income: $2684 Airbnb ROI: 2.35% Traditional ROI: 1.19%
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.	$174,000	Airbnb cash on cash: 7.64% Traditional cash on cash: 7.26% Airbnb Rental Income: $2403 Traditional Rental Income: $1752 Airbnb ROI: 7.64% Traditional ROI: 7.26%
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%
112 BRENT CIRCLE Oldsmar, FL Now Offered at $529,900 â Waterfront Townhome with Deeded Boat Slip in Oldsmar! This bea...	3 beds \| 3 baths \| 1,834 sq.ft.	$529,900	Airbnb cash on cash: 2.23% Traditional cash on cash: 2.13% Airbnb Rental Income: $3329 Traditional Rental Income: $2535 Airbnb ROI: 2.23% Traditional ROI: 2.13%
214 MEADOW LANE #214 Oldsmar, FL Clean and move-in ready Furnished 2/2 in The Meadows at East Lake Woodlands~~Income produc...	2 beds \| 2 baths \| 879 sq.ft.	$220,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 3.03% Airbnb Rental Income: $2403 Traditional Rental Income: $1669 Airbnb ROI: 3.73% Traditional ROI: 3.03%
1232 HOLLY CIRCLE Oldsmar, FL Welcome to a piece of paradise in Forest Lakes, Oldsmar, where peaceful living meets capti...	3 beds \| 2 baths \| 1,186 sq.ft.	$390,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 4.87% Airbnb Rental Income: $3329 Traditional Rental Income: $2347 Airbnb ROI: 5.52% Traditional ROI: 4.87%
321 SHORE DRIVE E Oldsmar, FL Welcome to this beautiful Home, fully remodeled ,4-bedroom, 2 bath. And step outside to yo...	4 beds \| 2 baths \| 1,523 sq.ft.	$465,000	Airbnb cash on cash: 6.32% Traditional cash on cash: 4.72% Airbnb Rental Income: $4558 Traditional Rental Income: $2913 Airbnb ROI: 6.32% Traditional ROI: 4.72%
150 POOLE PLACE Oldsmar, FL Welcome to this stunning, fully renovated 3 bedroom, 2 bathroom East Lake Woodlands villa ...	3 beds \| 2 baths \| 1,550 sq.ft.	$375,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 3.62% Airbnb Rental Income: $3329 Traditional Rental Income: $2340 Airbnb ROI: 4.32% Traditional ROI: 3.62%
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%
1630 GRAY BARK DRIVE Oldsmar, FL Under contract-accepting backup offers. Welcome home to 1630 Gray Bark Drive! This beautif...	3 beds \| 2 baths \| 1,358 sq.ft.	$465,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 3.13% Airbnb Rental Income: $3329 Traditional Rental Income: $2500 Airbnb ROI: 3.33% Traditional ROI: 3.13%
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.	$679,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 2.36% Airbnb Rental Income: $4558 Traditional Rental Income: $3177 Airbnb ROI: 3.05% Traditional ROI: 2.36%
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.	$375,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 2.95% Airbnb Rental Income: $3329 Traditional Rental Income: $2156 Airbnb ROI: 4.17% Traditional ROI: 2.95%
206 BEDFORD STREET Oldsmar, FL *PRICE IMPROVEMENT-MOTIVATED SELLER* This meticulously maintained 3 bedroom, 2 bath, 2...	3 beds \| 2 baths \| 1,274 sq.ft.	$399,900	Airbnb cash on cash: 4.73% Traditional cash on cash: 3.67% Airbnb Rental Income: $3329 Traditional Rental Income: $2189 Airbnb ROI: 4.73% Traditional ROI: 3.67%
140 DALE PLACE Oldsmar, FL TURN KEY VILLA perfect for Snow Birds, nestled in the GATED COMMUNITY of East Lake Woodlan...	3 beds \| 2 baths \| 1,445 sq.ft.	$368,500	Airbnb cash on cash: 3.93% Traditional cash on cash: 3.56% Airbnb Rental Income: $3329 Traditional Rental Income: $2457 Airbnb ROI: 3.93% Traditional ROI: 3.56%
347 COUNTRY CLUB DRIVE Oldsmar, FL Beautifully and Completely Refurbished Single Family Pool Home, (3) Bedrooms, (2) Baths wi...	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%
309 CONGRESS STREET Oldsmar, FL HIGH & DRY, NEVER FLOODED! Donât miss your chance to own this beautifully renovated like...	3 beds \| 2 baths \| 2,792 sq.ft.	$675,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 1.99% Airbnb Rental Income: $3329 Traditional Rental Income: $2240 Airbnb ROI: 2.53% Traditional ROI: 1.99%
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 High & Dry from the storms! Welcome to your dream home in the highly coveted neighborhood ...	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%
337 SHORE DRIVE E Oldsmar, FL OUTSTANDING PRICE for this RENOVATED HOME! Charming 3-Bedroom Home with Modern Updates & ...	3 beds \| 2 baths \| 1,100 sq.ft.	$323,000	Airbnb cash on cash: 6.08% Traditional cash on cash: 5.32% Airbnb Rental Income: $3329 Traditional Rental Income: $2352 Airbnb ROI: 6.08% Traditional ROI: 5.32%
1600 GRAY BARK DRIVE Oldsmar, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 3 baths \| 2,270 sq.ft.	$585,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 4.1% Airbnb Rental Income: $4558 Traditional Rental Income: $3415 Airbnb ROI: 4.46% Traditional ROI: 4.1%
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.	$225,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 3.34% Airbnb Rental Income: $2403 Traditional Rental Income: $1811 Airbnb ROI: 3.35% Traditional ROI: 3.34%
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%
122 E CYPRESS COURT #22 Oldsmar, FL One or more photo(s) has been virtually staged. Welcome to this 2-bedroom, 2-bathroom cond...	2 beds \| 2 baths \| 1,054 sq.ft.	$189,900	Airbnb cash on cash: 4.57% Traditional cash on cash: 4.5% Airbnb Rental Income: $2403 Traditional Rental Income: $1802 Airbnb ROI: 4.57% Traditional ROI: 4.5%
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 PRICE IMPROVEMENT! Immediate Rental Income Opportunity! Currently In-Law Suite Alone earns...	3 beds \| 2 baths \| 1,306 sq.ft.	$400,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 3.34% Airbnb Rental Income: $3329 Traditional Rental Income: $2103 Airbnb ROI: 4.62% Traditional ROI: 3.34%
145 BLUE MARLIN DRIVE Oldsmar, FL This spacious, contemporary residence offers the perfect blend of luxury and comfort, whet...	3 beds \| 2 baths \| 1,504 sq.ft.	$259,900	Airbnb cash on cash: 8.37% Traditional cash on cash: 6.71% Airbnb Rental Income: $3329 Traditional Rental Income: $2177 Airbnb ROI: 8.37% Traditional ROI: 6.71%
128 NANCY DRIVE #128 Oldsmar, FL Under contract-accepting backup offers. JUST REDUCED below $200K with HURRICANE IMPACT Win...	2 beds \| 2 baths \| 1,094 sq.ft.	$199,900	Airbnb cash on cash: 6.6% Traditional cash on cash: 6.5% Airbnb Rental Income: $2403 Traditional Rental Income: $1795 Airbnb ROI: 6.6% Traditional ROI: 6.5%
15 TADS TRAIL Oldsmar, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. OM...	3 beds \| 2 baths \| 1,550 sq.ft.	$299,900	Airbnb cash on cash: 5.18% Traditional cash on cash: 4.34% Airbnb Rental Income: $3329 Traditional Rental Income: $2347 Airbnb ROI: 5.18% Traditional ROI: 4.34%
313 JEFFERSON AVENUE S Oldsmar, FL Investor Special - Cash Offers Only. Own a piece of history with this Historic 3/2 home...	3 beds \| 2 baths \| 1,271 sq.ft.	$249,900	Airbnb cash on cash: 7.91% Traditional cash on cash: 6.71% Airbnb Rental Income: $3329 Traditional Rental Income: $2301 Airbnb ROI: 7.91% Traditional ROI: 6.71%
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.	$599,900	Airbnb cash on cash: 4.59% Traditional cash on cash: 3.35% Airbnb Rental Income: $4558 Traditional Rental Income: $2911 Airbnb ROI: 4.59% Traditional ROI: 3.35%

Vacation Rentals in Oldsmar

There are 71 vacation rental properties available for sale in the city of Oldsmar . The median list price of Airbnb properties available for sale in Oldsmar is $375,000 and the average price per square foot is $218. 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 71 Airbnb properties available for sale in Oldsmar.

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

In September 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

502 TIMBER BAY CIRCLE E

Oldsmar, FL

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

$448,000

Airbnb cash on cash: 6.17%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $4558

Traditional Rental Income: $2555

Airbnb ROI: 6.17%

Traditional ROI: 3.65%

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%

632 LAKE CYPRESS CIRCLE

Oldsmar, FL

4 beds | 2 baths | 1,906 sq.ft.

$563,000

Airbnb cash on cash: 4.66%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $4558

Traditional Rental Income: $2911

Airbnb ROI: 4.66%

Traditional ROI: 3.33%

436 LAFAYETTE BOULEVARD

Oldsmar, FL

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

$800,000

Airbnb cash on cash: 2.39%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $4558

Traditional Rental Income: $3466

Airbnb ROI: 2.39%

Traditional ROI: 2.2%

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.

$852,990

Airbnb cash on cash: 2.35%

Traditional cash on cash: 1.19%

Airbnb Rental Income: $4558

Traditional Rental Income: $2684

Airbnb ROI: 2.35%

Traditional ROI: 1.19%

134 SYCAMORE LANE #H

Oldsmar, FL

2 beds | 2 baths | 915 sq.ft.

$174,000

Airbnb cash on cash: 7.64%

Traditional cash on cash: 7.26%

Airbnb Rental Income: $2403

Traditional Rental Income: $1752

Airbnb ROI: 7.64%

Traditional ROI: 7.26%

150 TADS TRAIL

Oldsmar, FL

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%