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Search results; Over 1,000 homes in Oldsmar

Top guest favourite
Home in Oldsmar
Modern Private Estate | Central to Tampa & Beaches
3 bedrooms, 4 beds, 2.5 private bathrooms
14–19 Sept
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4.98 out of 5 average rating, 48 reviews
Guest favourite
Home in Oldsmar
Oldsmar Oasis
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Home in Oldsmar
Sunny Oasis: Villa Retreat
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 97 reviews
Guest favourite
Apartment in Oldsmar
Tampa Bay Getaway|Oldsmar | Heated Pool Condo
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Oldsmar
Sunny Florida Pool Escape
3 bedrooms, 5 beds, 2 bathrooms
31 Oct – 5 Nov
4.88 out of 5 average rating, 17 reviews
Home in Oldsmar
Florida Fun Villa
2 bedrooms, 2 beds, 2 bathrooms
4–9 Sept
New place to stay
Top guest favourite
Guest suite in Oldsmar
Lemon tree
1 bedroom, 1 queen bed, 1 bathroom
5–12 Sept
4.95 out of 5 average rating, 78 reviews
Guest favourite
Home in Oldsmar
Tropicoquette|Beach|Pool|Airport|Clearwater|STPete
3 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
5.0 out of 5 average rating, 5 reviews
Home in Oldsmar
Luxury Bayfront Escape
5 bedrooms, 6 beds, 4 bathrooms
4–9 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Safety Harbor
2/1 Modern City Stay | Best Downtown Location
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Guest house in Palm Harbor
Guesthouse with Pool in Palm Harbor
1 bedroom, 1 king bed, 1 bathroom
27 Oct – 1 Nov
4.98 out of 5 average rating, 113 reviews
Top guest favourite
Home in Palm Harbor
Steps to Downtown · Beach, Breweries, Trail
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Palm Harbor
Sandcastle Cottage close to beach and trail.
1 bedroom, 3 beds, 1 bathroom
4–9 Sept
4.96 out of 5 average rating, 24 reviews
Guest house in Tampa
The Yellow House Getaway #1
1 bedroom, 1 queen bed, 1 bathroom
16–21 Sept
New place to stay
Top guest favourite
Home in Clearwater
Game Room + Fire Pit Fun! • 2BR • 7 mi to Beach
2 bedrooms, 3 beds, 1 bathroom
5–10 Sept
5.0 out of 5 average rating, 38 reviews
Home in Tampa
Tampa Family Home/Private Pool /3 bedroom
3 bedrooms, 4 beds, 2 bathrooms
4–9 Sept
Home in Seminole
[6BR POOL VILLA] Pickleball+Games+MiniTheater+Golf
6 bedrooms, 8 beds, 3 bathrooms
7–12 Sept
New place to stay
Top guest favourite
Cottage in Safety Harbor
Safety Harbor Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 66 reviews
Top guest favourite
Home in Safety Harbor
Quiet Safety Harbor Retreat Near Clearwater Beach
2 bedrooms, 2 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 8 reviews