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Search results; Over 1,000 homes in Oldsmar

Photo 1 of 29
Top guest favourite
Cottage in Oldsmar
Louisa's Cottage
Studio, 1 bed, 2 private bathrooms
4–9 Oct
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4.96 out of 5 average rating, 324 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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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
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
1–6 Oct
New place to stay
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Home in Oldsmar
Luxury Bayfront Escape
5 bedrooms, 6 beds, 4 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 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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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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Top guest favourite
Cottage in Safety Harbor
Safety Harbor Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 66 reviews
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Home in Safety Harbor
Poolside Paradise
3 bedrooms, 4 beds, 2 bathrooms
2–9 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Room in Palm Harbor
Well Appointed 100% Private Room/Suite/Lake View
1 queen bed, 1 bathroom
4–9 Oct
4.96 out of 5 average rating, 273 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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Top guest favourite
Home in Palm Harbor
Checkmate Cottage | Fire Pit + Putting Green
2 bedrooms, 3 beds, 1 bathroom
2–7 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Palm Harbor
Casa St.George, Centrally Located, Pool, Game Room
5 bedrooms, 8 beds, 3 bathrooms
1–6 Oct
4.98 out of 5 average rating, 65 reviews
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Home in Oldsmar
Friendly Farmhouse Style Home
2 bedrooms, 3 beds, 2 bathrooms
24–29 Mar
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Guest favourite
Home in Safety Harbor
New Remodel - 1 Block from Water
3 bedrooms, 3 beds, 2 bathrooms
21–26 Oct
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Townhouse in Tampa
Tampa/Westchase 3BR Townhome I Family-Friendly
3 bedrooms, 6 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Palm Harbor
Endless Summer: Spacious Family Home Near Beaches
3 bedrooms, 5 beds, 2 bathrooms
17–22 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Safety Harbor
Downtown Safety Harbor • Walk to Main St • Arcade•
2 bedrooms, 3 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 48 reviews