Oldsmar Vacation Rentals, Villas & more


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Great rentals within 20 miles that match your search

1 / 31

Chateaux Condominium 407

  • 1
  • 2
  • 7 nights min

$147

Details

1 / 16

2 Bed / 2 Bath with View of the Bay

  • 2
  • 6
  • 28 nights min

$98

Details

1 / 22

Clearwater Bay Club 2 Bedroom Villa 1

  • 2
  • 5
  • Min stay varies

$140

Details

1 / 15

Clearwater Beach Home 100 Steps to the Gulf

  • 3
  • 6
  • 30 nights min

$114

Details

1 / 15

2 BR, 2 BA Surf Song Resort Townhouse #343 Next Availability Nov 11 - 18

  • 2
  • 4
  • 7 nights min

$87

Details

1 / 17

Art's Beach Retreat

  • 2
  • 6
  • 6 nights min

$222

Details

1 / 22

Sand Key Beach Front Studio

  • Studio
  • 4
  • 30 nights min

$61

Details

1 / 10

Redington Towers III Condominium 3-D

  • 2
  • 6
  • 28 nights min

$109

Details

1 / 25

(2024) Cozy Villa in Sunny Clearwater, Florida

  • 2
  • 4
  • Min stay varies

$89

Details

1 / 29

Oldest House on the Beach.Gulf Front, Built in 1891 3 Bedroom, 2 Bath-Sleep 6

  • 3
  • 6
  • 7 nights min

$217

Details

1 / 33

Sand Castle I Condominium 803

  • 3
  • 6
  • 7 nights min

$191

Details

1 / 14

Make New Memories

  • 2
  • 6
  • 5 nights min

$145

Details

1 / 23

Private Beach Bungalow - pet friendly

  • 2
  • 5
  • 7 nights min

$100

Details

1 / 19

Luxurious Beachfront Condo at Redington Towers

  • 2
  • 6
  • 30 nights min

$118

Details

1 / 23

Clearwater Fully Renovated Condo At Avalon

  • 1
  • 2
  • 7 nights min

$93

Details

1 / 28

Beach,Sunset,Shop,Fish or Fitness?

  • 2
  • 6
  • 7 nights min

$98

Details

1 / 16

Treasure Island Beachfront #1

  • 1
  • 4
  • 4 nights min

$109

Details

1 / 38

Sunset vistas 507 West Direct Gulf Front Unit

  • 2
  • 6
  • 5 nights min

$326

Details

1 / 11

6th Floor Dream Vacation Condo

  • 2
  • 6
  • 7 nights min

$114

Details

1 / 24

Beautiful Water Views - Updated Decor-Steps to the Beach

  • 2
  • 6
  • 7 nights min

$113

Details

1 / 14

Seaside Seclusion - Suite 3U

  • 2
  • 6
  • 1 night min

$355

Details

1 / 43

Beach Palms Condominium 507

  • 3
  • 7
  • 7 nights min

$201

Details

1 / 27

Top Floor Oceanview Condo @ Beach Cottage Resorts

  • 2
  • 4
  • Min stay varies

$155

Details

1 / 67

Clearwater Beach Budget Beauty

  • 1
  • 6
  • 3 nights min

$139

Details

1 / 28

The best guest rated condos at Madeira Beach area!

  • 1
  • 4
  • 4 nights min

$80

Details

1 / 30

Peace O'Paradise at Dolphin Pointe

  • 1
  • 4
  • 30 nights min

$65

Details

1 / 22

Beach Dreams - Beach Cottage 2103

  • 2
  • 6
  • 7 nights min

$167

Details

1 / 14

Lake Side/Park Vacation Getaway 10 Min from Beach

  • 2
  • 6
  • 2 nights min

$110

Details

1 / 21

On waters of Tampa Bay 3 mi from Tampa Int Airport

  • 1
  • 4
  • Min stay varies

$100

Details

1 / 24

Beautiful 3BR, 2BA South Causeway Isles Canal Home

  • 3
  • 8
  • Min stay varies

$236

Details

1 / 42

3 Bedrooms, sleep 8, Pet OK, Classic Beach House, Beach side, Hot Tub

  • 3
  • 8
  • Min stay varies

$310

Details

1 / 11

Luxury ground floor Condo for rent

  • 2
  • 4
  • 5 nights min

$70

Details

1 / 16

Cute Villa for renting in Oldsmar FL

  • 2
  • 4
  • 7 nights min

$201

Details

1 / 11

Beautiful Newly Renovated 2 Bedroom/2 Bath with BBQ & WIFI

  • 2
  • 4
  • 6 nights min

$100

Details

1 / 13

Newly Renovated Lakefront Condo

  • 2
  • 4
  • 60 nights min

$73

Details

1 / 14

Clean and Quite Private Room 1

  • 1
  • 2
  • 1 night min

$46

Details

1 / 16

Quite and Clean Private Room 2

  • 1
  • 2
  • 1 night min

$47

Details

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