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Holiday villas in Oldsmar, FL

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  • 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 338 Rentals in the Oldsmar Area
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From
€372
Per Week
Oldsmar
2 Bedrooms, 2 Bathrooms, Sleeps 6
7 photos Details
Reviews (6) Make Enquiry
5 of 5 stars Reviewed 2 May 2014
This place was clean and had lots of room. It was stocked with everything we needed. Great communication with the owner Pat as well as the property manager. The pool area was very...
5 of 5 stars Reviewed 23 June 2013
We rented this place because it was near the family. As soon as we arrived, we felt like home. Absolutely clean. It had everything we needed. Very quiet place. Comfortable rooms...
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From
€93
Per Night
Oldsmar
2 Bedrooms, 2 Bathrooms, Sleeps 5
11 photos Details
Reviews (1) Make Enquiry
1 of 5 stars Reviewed 2 May 2014
From the outside this property looks dated. On further inspection of this apparent wheelchair accessible vacation rental I could not access the property without help and getting...
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The following rentals are within 15 kilometers of Oldsmar, Florida.

From
€56
Per Night
Palm Harbor
1 Bedroom, 1 Bathroom, Sleeps 4
31 photos Details
Reviews (1) Make Enquiry
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Exclusive Quiet Beach Cottage
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1 Bedroom, sleeps 4
€74 - €96 / night
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3 Bedrooms, sleeps 6
€172 / night
The Ebb Tide - One Bedroom Condo
1 Bedroom, sleeps 2
€83 - €109 / night
From
€63
Per Night
Tarpon Springs
2 Bedrooms, 1 Bathroom, Sleeps 4
18 photos Details
Reviews (1) Make Enquiry
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5 of 5 stars Reviewed 21 June 2014
We travelled with 2 teenagers to stay at John & Linda's. They were gracious, caring hosts and their home is a comfortable retreat in a quaint, fun town. Take the bikes that they...
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From
€127
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 7
11 photos Details
Reviews (2) Make Enquiry
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4 of 5 stars Reviewed 16 May 2014
I did not rent through flip key I rented through craigslist . I have not received my deposit back after being told it would be refunded a few weeks ago. The house is very nice...
5 of 5 stars Reviewed 23 April 2014
The apartment was nice and clean. Close to the beach and good for families with kids. We even found thebbeach chairs and an umbrella in the closet. It was nice.
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From
€205
Per Night
Clearwater
4 Bedrooms, 3 Bathrooms, Sleeps 13
34 photos Details
Reviews (2) Make Enquiry
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5 of 5 stars Reviewed 10 July 2014
This was our first family vacation, and the house and cottage were perfect for our group of 13.. The house and cottage had everything we needed to make us feel at home, including...
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From
€37
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 3
13 photos Details
Reviews (4) Make Enquiry
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5 of 5 stars Reviewed 26 April 2014
i would most definately stay there again, and hope to make reservations around christmas time. the apt. was very easy to fine and Vicki the property owner was very easy to deal...
4 of 5 stars Reviewed 1 September 2013
We had a great time at this lovely little cottage. Vicki was a great host providing us with all we could need as amenities. When we needed information about the local towns and...
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From
€63
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 4
24 photos Details
Reviews (6) Make Enquiry
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5 of 5 stars Reviewed 25 October 2013
While attending a conference in Clearwater, my husband and I thought that this small, studio condo would provide a pleasant escape from the busy conference facility at the end of...
4 of 5 stars Reviewed 12 September 2013
Excellent location in easy reach of key amenities in lovely Clearwater Beach. Tons of helpful info provided by hosts. Condo was clean, stocked with games, key dishes/pots and...
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From
€54
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 2
9 photos Details
Reviews (2) Make Enquiry
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5 of 5 stars Reviewed 9 July 2014
My 15-year old daughter and I visited Clearwater for 5 nights and thoroughly enjoyed our stay. We rented a car so we could tour the area and the beaches. The apartment was...
4 of 5 stars Reviewed 7 May 2014
The carriage house is just perfect for one or a couple. It was very tidy. It is hidden behind the lovely hacienda and was very quiet. Bruce was very attentive and answered all...
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From
€67
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 4
28 photos Details
Reviews (4) Make Enquiry
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4 of 5 stars Reviewed 22 September 2013
If I return to Clearwater Beach I will return to this place, nice and clean pool, big balcony, dishwasher, Equipment for the beach with much towels, computer available with a good...
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From
€56
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 5
17 photos Details
Reviews (4) Make Enquiry
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5 of 5 stars Reviewed 30 June 2014
My 3 year old daughter, boyfriend, and I stayed here after 3 days in Orlando for a friends wedding and a very long and hot day at Disney world. We needed a vacation from our...
5 of 5 stars Reviewed 24 June 2014
My stay here was great! the place was clean and very very nice. the description by Vicki and the pictures were spot on. I cant imagine you could find a similar place with a...
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From
€42
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 4
38 photos Details
Reviews (2) Make Enquiry
From
€149
Per Night
Clearwater
3 Bedrooms, 3 Bathrooms, Sleeps 6
33 photos Details
Reviews (2) Make Enquiry
From
€417
Per Week
Clearwater
3 Bedrooms, 1 Bathroom, Sleeps 6
12 photos Details
Reviews (1) Make Enquiry
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5 of 5 stars Reviewed 28 March 2014
We came to Florida with 2 small boys (3 and 5) and stayed in this lovely home for a week. It really was a home away from home and offered everything you could possibly want. Fully...
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From
€133
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (1) Make Enquiry
From
€178
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 10
25 photos Details
Reviews (6) Make Enquiry
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5 of 5 stars Reviewed 21 May 2014
Do you want to be on the beach AND away from the crowds? Then this location is for you! The name says it all - 32 steps from the beach. That is accurate! And the beach is lovely...
5 of 5 stars Reviewed 20 May 2014
We had a delightful 11 night stay. The weather in early May was perfect as was the location in a quiet residential neighborhood but still within walking distance to the beach and...
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From
€298
Per Week
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 4
19 photos Details
Reviews (1) Make Enquiry
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4 of 5 stars Reviewed 27 March 2014
Nice apartment in a quiet condo, my son loved the swimming pool and played with other neighbours´ kids. Landlord was a fine gentleman and ensured we have a pleasant stay, provided...
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From
€56
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 4
13 photos Details
Reviews (2) Make Enquiry
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4 of 5 stars Reviewed 16 July 2014
The location was great! It says it sleeps four but is much better suited for 2. We were suppose to have 4 people in our group but at the last minute 2 people ended up not going...
5 of 5 stars Reviewed 14 May 2014
This was an amazing value in a fabulous location. Walking distance to great restaurants and of course the beautiful beach! Highly enjoyable!!
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From
€372
Per Night
Tarpon Springs
5 Bedrooms, 3 Bathrooms, Sleeps 10
107 photos Details
Reviews (8) Make Enquiry
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5 of 5 stars Reviewed 24 June 2014
Stayed at this wonderful house for a great week in June, 2014. Beautiful home with a great pool & sauna. Loved the view and the location was close to everything. The home is...
5 of 5 stars Reviewed 20 March 2014
We are four senior ladies that like to take a winter vacation somewhere warm. Because we have friends in Palm Harbor (nearby) we decided on this rental. So glad we did. The...
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From
€74
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 3
12 photos Details
Reviews (11) Make Enquiry
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4 of 5 stars Reviewed 20 June 2014
The cottage was nice and clean. The owner was very helpful to answer questions right away when asked. The beach was literally right across the street. The beach isn't crowded. It...
5 of 5 stars Reviewed 23 May 2014
The location was perfect--across the street from the beach and @ 1 mile to all the hotels and restaurants. It was clean, well-equipped and comfortable, and the landlord was...
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From
€28
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 3
50 photos Details
Reviews (3) Make Enquiry
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5 of 5 stars Reviewed 12 July 2014
We will definitely stay in this condo again. Nicely decorated, close to beaches & shopping. Excellent on site management. Wonderful pool. Quiet & gated community.
5 of 5 stars Reviewed 25 June 2014
This is a cute, cozy condo within a short drive from the beach and walkable to several restaurants. Grounds are well maintained, nice pool and exercise room. Owner is very...
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From
€86
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 6
35 photos Details
Reviews (4) Make Enquiry
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5 of 5 stars Reviewed 13 July 2014
My friend and I decided to take a last-minute trip to Florida. With less than a month to plan it, I found this little gem on trip advisor. We were looking for a place with a full...
5 of 5 stars Reviewed 18 June 2014
We stayed here for a week at the end of May. The unit had a good supply of everything needed to make our stay easy and fun. The kitchen was easy to work in and had more dishes...
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From
€74
Per Night
Palm Harbor
2 Bedrooms, 2 Bathrooms, Sleeps 4
15 photos Details
Reviews (1) Make Enquiry
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5 of 5 stars Reviewed 2 July 2014
We had the BEST time at Linda's Villa.. the Pinellas Trail offered a tranquil place for power walking and we even saw a turtle digging in the dirt off to the side! We walked out...
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From
€40
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 4
26 photos Details
Reviews (3) Make Enquiry
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5 of 5 stars Reviewed 15 July 2014
I travavelled with my partner and young son of 4 years old. The condo is in a great spot overlooking the pool. The condo itself is immaculate and very homely and has everything...
5 of 5 stars Reviewed 13 July 2014
This condo at Avalon, Clearwater exceeded our expectations. It was beautifully clean and well appointed, even down to the little touches- an emergency sewing kit came in very...
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From
€56
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (3) Make Enquiry
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5 of 5 stars Reviewed 7 July 2014
We stayed at this Condo for 1 week after we came of a Royal Caribbean cruise our first every cruise. We had a fantastic time on the cruise and we were thinking can or holiday get...
5 of 5 stars Reviewed 14 June 2014
We have just come back from this property and once again it meets the high standards that we have come to expect from Steve and Linda. There is a great mixture of privacy...
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From
€80
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 2
21 photos Details
Reviews (6) Make Enquiry
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4 of 5 stars Reviewed 21 July 2013
Enjoyed our stay at C-4. Small, but it is just what we expected and needed for the weekend. Great location in Clearwater Beach. Perfect weekend getaway. Wifi is spotty in...
3 of 5 stars Reviewed 1 July 2013
This was our first time staying at this vacation rental. The people who manage this resort are fantastic and the entire place has a "family like" atmosphere. The studio...
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From
€127
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (3) Make Enquiry
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5 of 5 stars Reviewed 23 June 2014
Everything was great. Beach and water uncrowded, Condo new ,clean and comfy, thanks for all the extras laundry soap paper plates, tissues toilet paper napkins...
5 of 5 stars Reviewed 9 September 2013
Enjoyed our time in Florida. Location was convenient but private and comfortable. So nice to enjoy the beach, the deck, the breezes and sunsets. Very comfortable and reasonably...
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From
€45
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 4
24 photos Details
Reviews (27) Make Enquiry
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5 of 5 stars Reviewed 19 May 2014
This condo has recently changed hands, the new owners are as approachable and helpful as the previous owners. The one bedroom apartment is very well appointed. There were several...
5 of 5 stars Reviewed 1 April 2014
We have stayed with Linda & Steve prior to this visit and they are always so Great to deal with. The condo is located in a great spot ...close to the beaches, all kinds of...
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From
€64
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 5
13 photos Details
Reviews (4) Make Enquiry
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4 of 5 stars Reviewed 15 July 2014
The place was perfect for our needs, a nice quiet holiday house in a friendly neighbourhood. A short drive to several very nice beaches and restaurants as well as having a nice...
4 of 5 stars Reviewed 31 December 2013
Once we were settled into the rental it became very much like home away from home. The owners Cathy and Paul were great and very accommodating even when they were suffering...
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From
€64
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details
Reviews (5) Make Enquiry
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5 of 5 stars Reviewed 8 July 2014
It was the first time our family went to Florida and it was perfect from the house to the weather. The Gillespie home made us feel very welcomed. It was just like the pictures in...
4 of 5 stars Reviewed 26 June 2014
The owners Cathy and Paul are a true pleasure to deal with with great communication and quick responses to questions and requests. The Villa is well kept and sits on a quiet...
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From
€298
Per Week
Tarpon Springs
1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details
Reviews (6) Make Enquiry
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5 of 5 stars Reviewed 10 August 2013
Quiet location with great amenities. nature walk saw a Rosetta Spoonbill which haven't seen in eight years. Highly recommend. Does need an good reading light by the...
5 of 5 stars Reviewed 6 June 2013
My friend and I stayed in this charming little apartment for a couple of days. Our stay there was Wonderful. The cost was so reasonable that we were not sure what to expect.We...
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From
€93
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 3
8 photos Details
Reviews (1) Make Enquiry
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3 of 5 stars Reviewed 26 May 2014
This unit was tastefully decorated and fully stocked with all the necessities for a nice stay. However, I don't see how it could be described by anyone as "ocean front." There...
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From
€32
Per Night
Clearwater
2 Bedrooms, 3 Bathrooms, Sleeps 4
10 photos Details
Reviews (2) Make Enquiry
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3 of 5 stars Reviewed 6 May 2014
We stayed in Iara's house for 6 nights. Our host is a heart-warming person who wants to make your stay comfortable. Her house is yours and besides your own bedroom with private...
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From
€67
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 2
11 photos Details
Reviews (1) Make Enquiry
From
€130
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 8
22 photos Details
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From
€92
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
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From
€37
Per Night
Dunedin
2 Bedrooms, 2 Bathrooms, Sleeps 4
7 photos Details
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From
€112
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 8
28 photos Details
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From
€45
Per Night
Dunedin
2 Bedrooms, 2 Bathrooms, Sleeps 4
9 photos Details
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From
€50
Per Night
Tarpon Springs
3 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Make Enquiry
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Suitability

  • Wheelchair access (35)
  • Elder access (113)
  • Suitable for children (141)
  • Pet friendly (59)
  • Smoking allowed (4)

Amenities

  • Internet (250)
  • Other outdoor space (243)
  • Air Conditioning (217)
  • All pools (188)
  • Grill (185)
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