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Search results; Over 1,000 homes in Oldsmar

Descriptions are based on details hosts provide
Top guest favourite
Home in Oldsmar
Bayside Retreat your tropical oasis
1 bedroom, 1 bed, 1 private bathroom
26–31 Jul
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5.0 out of 5 average rating, 167 reviews
Apartment in Oldsmar
Short drive to Honeymoon Island | Heated Pool
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Oldsmar
Screened pool, fire pit, and pool table
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 5 beds, 2 bathrooms
3–8 Aug
Guest favourite
Home in Oldsmar
Oldsmar Oasis
4.92 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Top guest favourite
Home in Oldsmar
Pool, grill, and 20 minutes from beach
4.96 out of 5 average rating, 90 reviews, 2 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
Home in Oldsmar
Luxury Bayfront Escape
New place to stay, 5 bedrooms, 6 beds, 4 bathrooms
26–31 Jul
Superhost
Home in Oldsmar
Pool, mini golf, and a fire pit
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
Top guest favourite
Apartment in Oldsmar
Gated community with a heated pool
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 2 bathrooms
14–21 Aug
Top guest favourite
Guest suite in Palm Harbor
Private Suite, 1 bedroom, 1 bathroom, pool, patio
4.97 out of 5 average rating, 385 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Cottage in Safety Harbor
Safety Harbor Cottage
5.0 out of 5 average rating, 66 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
Top guest favourite
Home in Palm Harbor
Saltwater pool and game room near beaches
4.98 out of 5 average rating, 64 reviews, 5 bedrooms, 8 beds, 3 bathrooms
17–22 Jul
Top guest favourite
Home in Dunedin
Heated pool and screened-in lanai
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Jul
Guest favourite
Home in Palm Harbor
Fire pit, putting green, and giant chess
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Jul
Top guest favourite
Home in Clearwater
Heated pool, jacuzzi, and EV charger
4.99 out of 5 average rating, 91 reviews, 4 bedrooms, 5 beds, 2 bathrooms
5–10 Aug
Top guest favourite
Home in Palm Harbor
Lakefront retreat with a private swim spa
4.98 out of 5 average rating, 45 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Guest favourite
Flat in Palm Harbor
2BRCondo In Palm Harbor With Pool!
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
Top guest favourite
Villa in Palm Harbor
Renovated townhome with pool and grill
5.0 out of 5 average rating, 49 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
18–23 Jul
Top guest favourite
Home in Clearwater
Sunset Palms Retreat!
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Guest suite in Safety Harbor
Suite Outlook-Upstairs unit with Spectacular views
4.99 out of 5 average rating, 295 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul