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Vacation Rentals in Oldsmar, FL and nearby

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All 350 Rentals in the Oldsmar Area
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From
$95
Per Night
Oldsmar
2 Bedrooms, 2 Bathrooms, Sleeps 5
13 photos Details Reviews (1) Make Inquiry
From
$500
Per Week
Oldsmar
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
7 photos Details Reviews (6) Make Inquiry
From
$5,180
Per Month
Oldsmar
2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details Make Inquiry
Also consider
Villa Crystal - 5 Bdrs - Private Pool
5 Bedrooms, sleeps 10
$427 - $1,141 / night
Modern up dated home 3 streets from Gulf of Mexico
2 Bedrooms, sleeps 4
$114 / night
Gorgeous Margaritaville Pool Home - Private Pool
3 Bedrooms, sleeps 10
$229 - $375 / night
Ashley's Greek Sponge Docks Tarpon Springs Rental
3 Bedrooms, sleeps 10
$129 / night

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

From
$99
Per Night
Palm Harbor
2 Bedrooms, 2 Bathrooms, Sleeps 4
15 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 2, 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
$275
Per Night
Clearwater
4 Bedrooms, 3 Bathrooms, Sleeps 13
Booking
34 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed July 9, 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
$325
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
16 photos Details Reviews (7) Make Inquiry
5 of 5 stars Reviewed December 31, 2013
We enjoyed this wonderful house for a week. Perfect place to stay. Place is well maintained and tastefully decorated. The location is outstanding, close to the beach and downtown...
5 of 5 stars Reviewed August 19, 2012
I can't say enough about this beach house and its owners Angel & Linda there the best,and Linda,sorry about all the time i bugged you about for stupid things. The Beach house and...
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From
$225
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
25 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed May 21, 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 May 20, 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
$100
Per Night
Palm Harbor
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
29 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed August 3, 2014
The property is very well kept. The rental was extremely nice. We have stayed in very nice hotels and rentals and this rental beats all of them. The rental even had lounge...
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From
$275
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 22, 2014
Our stay at Seaside was wonderful, just what the doctor ordered! The condo was clean, well appointed with everything we needed. Beds were clean and comfy, kitchen had everything...
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From
$400
Per Week
Tarpon Springs
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
11 photos Details Reviews (7) Make Inquiry
5 of 5 stars Reviewed August 3, 2014
Were stayed here last March and April. Cheryl made it all work, a great host. Close to all beaches and shopping, but hidden near the shore, and you have so much privacy. We...
5 of 5 stars Reviewed August 10, 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...
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From
$100
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 3
Bookings
12 photos Details Reviews (12) Make Inquiry
5 of 5 stars Reviewed August 26, 2014
My husband and I recently returned from our kids-free getaway, where we stayed at the cottage. When we first arrived we weren't sure about the size (is kind of small), but turns...
4 of 5 stars Reviewed June 19, 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...
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From
$500
Per Night
Tarpon Springs
5 Bedrooms, 3 Bathrooms, Sleeps 10
107 photos Details Reviews (8) Make Inquiry
5 of 5 stars Reviewed June 24, 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 March 20, 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
$85
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 4
Bookings
28 photos Details Reviews (4) Make Inquiry
4 of 5 stars Reviewed September 22, 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
$80
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 5
Bookings
17 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed October 13, 2014
This place was exactly as described on TripAdvisor. I couldn't give a more positive recommendation on a place to stay in Dunedin, FL. Vicky's rental was very nice and ready to...
5 of 5 stars Reviewed June 30, 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...
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From
$50
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 3
Bookings
17 photos Details Reviews (5) Make Inquiry
4 of 5 stars Reviewed September 21, 2014
Very cute little cottage. Close to the beach.Perfect for one or couple looking to be out of typical hotel scene. Lovely garden and surroundings.Would definitely rebook.
5 of 5 stars Reviewed April 25, 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...
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From
$85
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 4
Bookings
24 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed October 25, 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 September 11, 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 4
Bookings
34 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed July 24, 2014
My stay at the Avalon at Clearwater went beyond my expectations - it was a delightful stay in a beautiful complex with amazing accommodations, pool and close to restaurants...
5 of 5 stars Reviewed July 17, 2014
Oh, my gosh, where to begin, the condo was perfect, spotless clean. We were kind of anxious to bring our teens with us, you know how kids can be picky today. They loved the...
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From
$142
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
9 photos Details Reviews (7) Make Inquiry
5 of 5 stars Reviewed July 12, 2014
My daughter and I stayed in the lower level studio. It was perfect for the two of us. Very clean, updated unit. A few steps from the white sand and beautiful sunsets. We did not...
5 of 5 stars Reviewed June 15, 2014
My husband and I stayed at this wonderful place for 3 days and had a great time! We recommend anyone wanting to slip away to a tropical paradise to stay here! The owners are very...
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From
$165
Per Night
Clearwater
Studio, 1 Bathroom, Sleeps 2
Bookings
15 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed May 8, 2014
We stayed here for 10 days and thoroughly enjoyed our time here. Tastefully furnished - with everything you would need. As Angel says - just steps from that perfect Clearwater...
4 of 5 stars Reviewed November 10, 2013
The photo of the porch had sold us on choosing this property. And we were not disappointed..The unit is on the 2nd floor of what once was a private home, and has been updated with...
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From
$275
Per Night
Clearwater
3 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
17 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed August 9, 2014
Very well equipped and comfortable townhouse within walking distance of the beach and Clearwater shops and restaurants. Located on the waters edge we were lucky enough to see...
5 of 5 stars Reviewed August 3, 2014
You will not be disappointed. We are only into out second day of a week long stay and felt compelled to write a review so soon as we are so pleased with the location (proximity to...
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From
$55
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
17 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 18, 2014
My husband and I decided to stay here for our vacation we love it! It is a home away from home. If you like big box hotels then this is not the room for you. Now if you like to go...
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From
$47
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 4
24 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed October 20, 2014
We stayed in this elegant condo for a week in the beginning of October. Our initial reaction entering the Avalon complex was very gratifying. We were impressed with the...
5 of 5 stars Reviewed August 12, 2014
We arrived at this newly renovated, luxurious condo and were so excited to see what a beautiful condo it is. The pictures don't do it justice. The property is accurately...
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From
$116
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 6
Bookings
35 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed July 13, 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 June 17, 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
$86
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
13 photos Details Reviews (5) Make Inquiry
4 of 5 stars Reviewed August 4, 2014
Stayed for a week and had a great time in Florida. This home worked out quite well for us. The home was well kept and had most of what you would need for a long stay. Very...
4 of 5 stars Reviewed July 14, 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...
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From
$179
Per Night
Clearwater
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
15 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed July 31, 2014
My family and I stayed here from July 5 to July 12, 2014. (3 teenagers) First impressions mean a lot and this one did not disappoint! The condo is spectacular. Nicely decorated...
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From
$85
Per Night
Tarpon Springs
2 Bedrooms, 1 Bathroom, Sleeps 4
18 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed June 21, 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
$86
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
25 photos Details Reviews (7) Make Inquiry
4 of 5 stars Reviewed August 26, 2014
The condo was nice and well equipped. Located very close to Clearwater Beach and not far to other beaches as well. We had a great time!!
4 of 5 stars Reviewed August 10, 2014
We appreciated finding a place so close to our daughter. Cathy was incredibly easy to work with. She helped in every situation we asked her. We even asked to get in two days...
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From
$38
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
50 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed July 12, 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 June 25, 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
$125
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
8 photos Details Reviews (1) Make Inquiry
3 of 5 stars Reviewed May 26, 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
$178
Per Night
Clearwater
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
14 photos Details Make Inquiry
From
$90
Per Night
Tarpon Springs
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
58 photos Details Make Inquiry
From
$95
Per Night
Palm Harbor
3 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details Make Inquiry
From
$100
Per Night
Palm Harbor
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details Make Inquiry
From
$299
Per Night
Clearwater
4 Bedrooms, 3 Bathrooms, Sleeps 12
Bookings
23 photos Details Make Inquiry
From
$250
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 2
6 photos Details Make Inquiry
From
$74
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
24 photos Details Make Inquiry
From
$67
Per Night
Tarpon Springs
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
22 photos Details Make Inquiry
From
$85
Per Night
Tarpon Springs
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
15 photos Details Make Inquiry
From
$98
Per Night
Clearwater
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
19 photos Details Make Inquiry
From
$99
Per Night
Clearwater
1 Bedroom, 1 Bathroom, Sleeps 1
5 photos Details Make Inquiry
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Book Online(139)

Suitability

  • Wheelchair access (37)
  • Elder access (111)
  • Suitable for children (143)
  • Pet friendly (65)
  • Smoking allowed (6)

Amenities

  • Internet (304)
  • Other outdoor space (278)
  • Air Conditioning (266)
  • Washer/Dryer (234)
  • Parking (214)
  • View all amenities