Best price vacation rentals in Oldsmar, FL, USA • 150 Listings
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Oldsmar, FL, USA Vacation Rentals | 

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5.0 (52)
Casa del Tren - Rare Availability + Serious Fun!
Up to 4 guests
Vrbo$314
Airbnb$321
Average Nightly Rate
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5.0 (62)
Safety Harbor Getaway Villa with Pool
Up to 10 guests
Vrbo$265
Airbnb$288
Average Nightly Rate
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5.0 (69)
🔆Modern Coastal Cottage🔆 Pool, Beaches, near Downtown Dunedin
Up to 8 guests
Airbnb$295
Vrbo$295
Average Nightly Rate
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5.0 (91)
Villa Italia - Italian Charm meets 21st Century Downtown Safety Harbor -
Up to 4 guests
Airbnb$207
Vrbo$207
Average Nightly Rate
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5.0 (72)
Villa Key West - Key West charm meets 21st century - Downtown Safety Harbor
Up to 4 guests
Vrbo$179
Airbnb$199
Average Nightly Rate
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5.0 (209)
Maison De L'eau Douce
Up to 4 guests
Airbnb$120
Vrbo$120
Average Nightly Rate
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5.0 (16)
Florida Home on Private Fishing Pond- See Nature not Neighbors
Up to 6 guests
Airbnb$105
Vrbo$132
Average Nightly Rate

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5.0 (70)
Tarpon Lake Escape LLC
Up to 6 guests
Airbnb$182
Vrbo$182
Average Nightly Rate
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5.0 (33)
Blue Bayou Inn - Room 5 of 7
Up to 2 guests
Airbnb$145
Vrbo$145
Average Nightly Rate

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5.0 (21)
Casa Tropicál - saltwater pool, near top beaches
Up to 4 guests
Airbnb$241
Vrbo$251
Average Nightly Rate
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5.0 (70)
Clearwater! HUGE VILLA 3500 sqft BIG LOT with HEATED POOL near Beach and Golf...
Up to 14 guests
Vrbo$613
Airbnb$819
Average Nightly Rate
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5.0 (84)
AMAZING LARGE 2000 SQ FT VACATION POOL & HOT TUB HOME CLEARWATER / DUNEDIN !
Up to 8 guests
Airbnb$311
Vrbo$330
Average Nightly Rate
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5.0 (4)
NEW! Home w/ Fire Pit - 5 Mi to Clearwater Beach!
Up to 6 guests
Vrbo$109
Airbnb$125
Average Nightly Rate
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5.0 (6)
Renovated Waterfront Getaway
Up to 6 guests
Vrbo$449
Airbnb$550
Average Nightly Rate
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5.0 (16)
Tropical Palm Harbor Retreat with Lanai & Patio!
Up to 5 guests
Airbnb$210
Vrbo$227
Average Nightly Rate
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5.0 (16)
Heated Pool☀️2 miles downtown Dunedin 🌴Near Honeymoon Isl & CLW Beach🍹WIFI✨Clean
Up to 6 guests
Vrbo$418
Airbnb$459
Average Nightly Rate
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5.0 (31)
Safety Harbor Bird House with Lake View
Up to 6 guests
Airbnb$175
Vrbo$175
Average Nightly Rate
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5.0 (46)
Modern House, Heated Pool, Fenced, Beaches, Relax
Up to 8 guests
Airbnb$522
Vrbo$565
Average Nightly Rate
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5.0 (1)
Prestwick 3129 at Innisbrook
Up to 4 guests
Vrbo$159
Airbnb$161
Average Nightly Rate
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5.0 (8)
Lake Tarpon/Waterfront/HUGE House/HUGE POOL/ Lots Of Wildlife/Kayaks Included
Up to 14 guests
Airbnb$672
Vrbo$672
Average Nightly Rate
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5.0 (1)
Coastal Zen w/ Pool and Private Dock
Up to 6 guests
Airbnb$271
Vrbo$351
Average Nightly Rate
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5.0 (6)
Welcome to Howard Beach Hideaway
Up to 10 guests
Airbnb$517
Vrbo$726
Average Nightly Rate
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5.0 (5)
Waterfront Tropical Oasis with its own Private Beach and Kayak launch Dock!
Up to 16 guests
Airbnb$1,643
Vrbo$1,971
Average Nightly Rate
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5.0 (18)
Spacious home - 4 bedrooms (2 Kings suites), sleeps 10, heated pool, fast WiFi
Up to 10 guests
Vrbo$365
Airbnb$387
Average Nightly Rate
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5.0 (10)
NEW! Bright Largo Home w/ Pool ~ 7 Mi to Beaches!
Up to 10 guests
Airbnb$388
Vrbo$1,116
Average Nightly Rate
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  3. Oldsmar Vacation Rental Price Comparison

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