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Search results; Over 1,000 homes in Oldsmar

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Top guest favourite
Place to stay in Oldsmar
Bayside Retreat your tropical oasis
1 bedroom, 1 bed, 1 private bathroom
19–24 Sept
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5.0 out of 5 average rating, 170 reviews
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Top guest favourite
Home in Oldsmar
Sunny Oasis: Villa Retreat
2 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
4.96 out of 5 average rating, 99 reviews
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Guest favourite
Home in Oldsmar
Oldsmar Oasis
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.92 out of 5 average rating, 12 reviews
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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
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Home in Oldsmar
Florida Fun Villa
2 bedrooms, 2 beds, 2 bathrooms
19–24 Sept
New place to stay
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Top guest favourite
Guest suite in Oldsmar
Lemon tree
1 bedroom, 1 queen bed, 1 bathroom
18–25 Oct
4.95 out of 5 average rating, 78 reviews
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Guest favourite
Home in Oldsmar
Tropicoquette|Beach|Pool|Airport|Clearwater|STPete
3 bedrooms, 5 beds, 3 bathrooms
14–19 Oct
5.0 out of 5 average rating, 5 reviews
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Home in Oldsmar
Luxury Bayfront Escape
5 bedrooms, 6 beds, 4 bathrooms
19–24 Sept
5.0 out of 5 average rating, 4 reviews
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Cottage in Safety Harbor
Safety Harbor Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 66 reviews
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Home in Palm Harbor
Sandcastle Cottage close to beach and trail.
1 bedroom, 3 beds, 1 bathroom
19–24 Sept
4.96 out of 5 average rating, 24 reviews
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Guest house in Tampa
Cottage in Paradise.
2 bedrooms, 3 beds, 1.5 bathrooms
26 Sept – 2 Oct
4.99 out of 5 average rating, 106 reviews
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Guest suite in Clearwater
Clearwater Studio Getaway
1 bedroom, 1 queen bed, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 152 reviews
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Home in Tampa
House at North Tampa 3BR & 2BA + Backyard
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.93 out of 5 average rating, 194 reviews
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Tiny home in Dunedin
Blessed Address
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 42 reviews
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Guest favourite
Home in Safety Harbor
2/1 Modern City Stay | Best Downtown Location
2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
4.93 out of 5 average rating, 14 reviews
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Top guest favourite
Guest house in Tampa
Hidden Gem • Stylish & Insta-Ready • Free Decor
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 37 reviews
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Home in Palm Harbor
Steps to Downtown · Beach, Breweries, Trail
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Room in Palm Harbor
Private Suite, 1 bedroom, 1 bathroom, pool, patio
1 king bed, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 396 reviews
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Home in Safety Harbor
Poolside Paradise
3 bedrooms, 4 beds, 2 bathrooms
25 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews