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Vacation Rentals in Oldsmar, FL and nearby

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 339 Rentals in the Oldsmar Area
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From
$500
Per Week
Oldsmar
2 Bedrooms, 2 Bathrooms, Sleeps 6
7 photos Details
Reviews (6) Make Inquiry
From
$125
Per Night
Oldsmar
2 Bedrooms, 2 Bathrooms, Sleeps 5
11 photos Details
Reviews (1) Make Inquiry

The following rentals are within 10 miles of Oldsmar, Florida.

From
$24,000
Per Month
Clearwater
4 Bedrooms, 3 Bathrooms, Sleeps 11
30 photos Details
Reviews (1) Make Inquiry
Also consider
Clearwater Beach Furnished Condo
2 Bedrooms, sleeps 4
$92 / night
NEW – Elegant Waterside Escape (Not Available)
1 Bedroom, sleeps 4
$59 / night
The Sunset House / Beach Front with Pool & Hot Tub
5 Bedrooms, sleeps 13
$1,071 / night
Exclusive Tropical Retreat in Sunny Clearwater Beach
4 Bedrooms, sleeps 12
$299 - $349 / night
From
$4,500
Per Month
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 4
11 photos Details
Reviews (5) Make Inquiry
From
$1,300
Per Week
Clearwater
3 Bedrooms, 3 Bathrooms, Sleeps 8
28 photos Details
Reviews (27) Make Inquiry
From
$1,300
Per Week
Clearwater
3 Bedrooms, 3 Bathrooms, Sleeps 8
30 photos Details
Reviews (35) Make Inquiry
From
$57
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 4
38 photos Details
Reviews (2) Make Inquiry
From
$75
Per Night
Palm Harbor
1 Bedroom, 1 Bathroom, Sleeps 4
31 photos Details
Reviews (1) Make Inquiry
Get the List
From
$125
Per Night
Dunedin
2 Bedrooms, 1 Bathroom, Sleeps 4
38 photos Details
Reviews (2) Make Inquiry
From
$400
Per Week
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 4
19 photos Details
Reviews (1) Make Inquiry
From
$275
Per Night
Clearwater
4 Bedrooms, 3 Bathrooms, Sleeps 13
34 photos Details
Reviews (2) Make Inquiry
From
$179
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (1) Make Inquiry
From
$170
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 7
11 photos Details
Reviews (2) Make Inquiry
From
$560
Per Week
Clearwater
3 Bedrooms, 1 Bathroom, Sleeps 6
12 photos Details
Reviews (1) Make Inquiry
From
$200
Per Night
Clearwater
3 Bedrooms, 3 Bathrooms, Sleeps 6
33 photos Details
Reviews (2) Make Inquiry
From
$75
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 5
17 photos Details
Reviews (4) Make Inquiry
From
$90
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 4
28 photos Details
Reviews (4) Make Inquiry
From
$85
Per Night
Tarpon Springs
2 Bedrooms, 1 Bathroom, Sleeps 4
18 photos Details
Reviews (1) Make Inquiry
From
$75
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 4
13 photos Details
Reviews (1) Make Inquiry
From
$788
Per Week
Clearwater
1 Bedroom, 2 Bathrooms, Sleeps 2
13 photos Details
Reviews (2) Make Inquiry
From
$50
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 3
13 photos Details
Reviews (4) Make Inquiry
From
$1,155
Per Week
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 8
28 photos Details
Reviews (1) Make Inquiry
From
$85
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 4
24 photos Details
Reviews (6) Make Inquiry
From
$100
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 3
12 photos Details
Reviews (11) Make Inquiry
From
$72
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 2
9 photos Details
Reviews (2) Make Inquiry
From
$239
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 10
25 photos Details
Reviews (6) Make Inquiry
From
$2,968
Per Week
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (4) Make Inquiry
From
$150
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 6
27 photos Details
Reviews (3) Make Inquiry
From
$99
Per Night
Palm Harbor
2 Bedrooms, 2 Bathrooms, Sleeps 4
15 photos Details
Reviews (1) Make Inquiry
From
$500
Per Night
Tarpon Springs
5 Bedrooms, 3 Bathrooms, Sleeps 10
107 photos Details
Reviews (8) Make Inquiry
From
$200
Per Night
Dunedin
2 Bedrooms, 1 Bathroom, Sleeps 4
12 photos Details
Reviews (10) Make Inquiry
From
$275
Per Night
Clearwater
3 Bedrooms, 3 Bathrooms, Sleeps 6
17 photos Details
Reviews (3) Make Inquiry
From
$160
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 8
28 photos Details
Reviews (3) Make Inquiry
From
$5,700
Per Month
Clearwater
3 Bedrooms, 3 Bathrooms, Sleeps 8
18 photos Details
Reviews (2) Make Inquiry
From
$1,155
Per Week
Clearwater
3 Bedrooms, 3 Bathrooms, Sleeps 8
26 photos Details
Reviews (1) Make Inquiry
From
$38
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 3
50 photos Details
Reviews (2) Make Inquiry
From
$167
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (3) Make Inquiry
From
$295
Per Night
Clearwater
4 Bedrooms, 3 Bathrooms, Sleeps 10
16 photos Details
Reviews (5) Make Inquiry
From
$499
Per Night
Clearwater
4 Bedrooms, 3 Bathrooms, Sleeps 10
23 photos Details
Reviews (1) Make Inquiry
From
$1,300
Per Week
Clearwater
3 Bedrooms, 3 Bathrooms, Sleeps 8
30 photos Details
Reviews (34) Make Inquiry
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Book Online(148)
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Suitability

  • Wheelchair access (35)
  • Elder access (113)
  • Suitable for children (143)
  • Pet friendly (59)
  • Smoking allowed (4)

Amenities

  • Internet (252)
  • Other outdoor space (245)
  • Air Conditioning (218)
  • All pools (190)
  • Grill (187)
  • View all amenities
Filter search results by:
Book Online(148)

Suitability

  • Wheelchair access (35)
  • Elder access (113)
  • Suitable for children (143)
  • Pet friendly (59)
  • Smoking allowed (4)

Amenities

  • Internet (252)
  • Other outdoor space (245)
  • Air Conditioning (218)
  • All pools (190)
  • Grill (187)
  • View all amenities