We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Villas in Oldsmar, Florida

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
Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 293 Rentals in the Oldsmar Area
loading...
From
£292
Per Week
Oldsmar
2 Bedrooms, 2 Bathrooms, Sleeps 6
7 photos Details
Reviews (6) Make Enquiry
From
£73
Per Night
Oldsmar
2 Bedrooms, 2 Bathrooms, Sleeps 5
11 photos Details
Reviews (1) Make Enquiry

The following rentals are within 15 kilometres of Oldsmar, Florida.

From
£292
Per Night
Tarpon Springs
5 Bedrooms, 3 Bathrooms, Sleeps 10
107 photos Details
Reviews (8) Make Enquiry
Also consider
2 Heated Pools, Tangerine Dream Cottage
2 Bedrooms, sleeps 6
£71 - £158 / night
Sea Breeze, Clearwater Beach
4 Bedrooms, sleeps 10
£2,165 - £2,783 / week
Gulf/Beach Front Condo
2 Bedrooms, sleeps 6
£146 - £233 / night
Cabana Spa House - 30 sec. to beach. Great rates!
2 Bedrooms, sleeps 4
£758 - £1,459 / week
From
£42
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 2
9 photos Details
Reviews (1) Make Enquiry
From
£99
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 7
11 photos Details
Reviews (2) Make Enquiry
From
£104
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (1) Make Enquiry
From
£44
Per Night
Palm Harbor
1 Bedroom, 1 Bathroom, Sleeps 4
31 photos Details
Reviews (1) Make Enquiry
From
£22
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 3
50 photos Details
Reviews (2) Make Enquiry
Get the List
From
£29
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 3
13 photos Details
Reviews (4) Make Enquiry
From
£53
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 4
28 photos Details
Reviews (4) Make Enquiry
From
£198
Per Night
Clearwater
4 Bedrooms, 3 Bathrooms, Sleeps 13
34 photos Details
Reviews (1) Make Enquiry
From
£68
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 6
35 photos Details
Reviews (3) Make Enquiry
From
£58
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 3
12 photos Details
Reviews (11) Make Enquiry
From
£50
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 4
24 photos Details
Reviews (6) Make Enquiry
From
£44
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 5
17 photos Details
Reviews (2) Make Enquiry
From
£117
Per Night
Clearwater
3 Bedrooms, 3 Bathrooms, Sleeps 6
33 photos Details
Reviews (2) Make Enquiry
From
£139
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 10
25 photos Details
Reviews (6) Make Enquiry
From
£41
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 4
13 photos Details
Reviews (1) Make Enquiry
From
£327
Per Week
Clearwater
3 Bedrooms, 1 Bathroom, Sleeps 6
12 photos Details
Reviews (1) Make Enquiry
From
£233
Per Week
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 4
19 photos Details
Reviews (1) Make Enquiry
From
£50
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 5
13 photos Details
Reviews (3) Make Enquiry
From
£63
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 2
21 photos Details
Reviews (6) Make Enquiry
From
£100
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (3) Make Enquiry
From
£35
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 4
24 photos Details
Reviews (27) Make Enquiry
From
£44
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (2) Make Enquiry
From
£33
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 4
33 photos Details
Reviews (2) Make Enquiry
From
£1,732
Per Week
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (4) Make Enquiry
From
£50
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details
Reviews (4) Make Enquiry
From
£50
Per Night
Tarpon Springs
2 Bedrooms, 1 Bathroom, Sleeps 4
18 photos Details
Reviews (1) Make Enquiry
From
£233
Per Week
Tarpon Springs
1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details
Reviews (6) Make Enquiry
From
£53
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 2
11 photos Details
Reviews (1) Make Enquiry
From
£73
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 3
8 photos Details
Reviews (1) Make Enquiry
From
£25
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details
Reviews (2) Make Enquiry
From
£102
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 8
22 photos Details
Make Enquiry
From
£44
Per Night
Tarpon Springs
1 Bedroom, 1 Bathroom, Sleeps 4
15 photos Details
Make Enquiry
From
£1,208
Per Month
Tarpon Springs
2 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details
Make Enquiry
From
£265
Per Week
Dunedin
2 Bedrooms, 2 Bathrooms, Sleeps 4
11 photos Details
Make Enquiry
From
£50
Per Night
Palm Harbor
3 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details
Make Enquiry
From
£48
Per Night
Crystal Beach
3 Bedrooms, 2 Bathrooms, Sleeps 5
12 photos Details
Make Enquiry
From
£4,085
Per Night
Clearwater
3 Bedrooms, 4 Bathrooms, Sleeps 8
4 photos Details
Make Enquiry
Go to map view
Book Online(142)
Use filters to find the best results!

Suitability

  • Wheelchair access (30)
  • Elder access (112)
  • Suitable for children (142)
  • Pet friendly (42)
  • Smoking allowed (2)

Amenities

  • Internet (214)
  • Other outdoor space (206)
  • Air Conditioning (174)
  • All pools (163)
  • Grill (159)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities