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Oldsmar Vacation Rentals & Homes - 40 Rentals Available

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40 Vacation rentals near Oldsmar

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(8)

1 / 5

Palm Harbor Condo - 2.8 miles away

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning
“this is 3rd year staying there, fully equipped from tin foil to beach supplies. Comfortable, great place to stay. Home away from home...”
- Review left on 04/21/2016

$71

Very Good (8 reviews)

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from $71 / night

(18)

1 / 19

Clearwater House - 4.5 miles away

  • 5
  • 6
  • 1 night min
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
“Ellen was wonderful, her home beautiful, accommodations were comfortable and just what we needed! Ellen was helpful with suggestions for beaches and offered discounts for area attractions...”
- Review left on 04/20/2016

$85

Excellent (18 reviews)

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from $85 / night

(10)

1 / 27

Tampa House - 6.2 miles away

  • 4
  • 8
  • Min stay varies
  • Nearest beach 26 mi
  • Swimming pool
  • Ask about children

$225

Excellent (10 reviews)

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from $225 / night

(8)

1 / 15

Palm Harbor Townhouse - 6.6 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“My husband and I are just completing our 3 month stay at this townhouse. We have enjoyed it so much that we are coming back again next year...”
- Review left on 03/27/2016

$54

Excellent (8 reviews)

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from $54 / night

(2)

1 / 11

Palm Harbor Condo - 6.9 miles away

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“When we found this condo, it almost sounded too good to be true, but I have to say it exceeded our expectations! the Innisbrook Property is outstanding. Well maintained, excellent amenities and just a beautiful place to be for many activities. Our...”
- Review left on 03/06/2016

$99

Excellent (2 reviews)

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from $99 / night

1 / 12

Dunedin Studio - 7.1 miles away

  • -1
  • 3
  • Min stay varies
  • Child friendly
  • Air conditioning

from $189 / night

1 / 27

Tampa House - 7.7 miles away

  • 4
  • 10
  • 4 nights min
  • Child friendly
  • Pet friendly

$325

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from $325 / night

(31)

1 / 16

Dunedin Condo - 7.8 miles away

  • 2
  • 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“Four of us stayed for one week, we wish it could have been longer. Our host were great, we were taken out in the 18 ft. boat and shown how to run it and were to fish, it ran like a top.The people staying in the other three units were friendly. The...”
- Review left on 02/18/2017

$183

Excellent (31 reviews)

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from $183 / night

(3)

1 / 70

Tampa House - 7.8 miles away

  • 4
  • 13
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 41 mi
  • Swimming pool
“We came to have our wedding in st Petersburg on pass a grille beach July 8 we want a place to spend time with family as our families are coming together!! This home was PERFECT! The owners are AMAZING!! LOVED EVERY MOMENT THERE! Didn't want to leave...”
- Review left on 07/12/2016

$350

Very Good (3 reviews)

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from $350 / night

1 / 24

Dunedin Villa - 8.4 miles away

  • 8
  • 16
  • 127 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$600

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from $600 / night

1 / 25

Clearwater House - 8.5 miles away

  • 3
  • 14
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $250 / night

(14)

1 / 10

Tampa House - 8.8 miles away

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“House was very clean and nicely furnished for five. Perfect location for access to all of our activities during the week and in a quiet neighborhood with great views. Property manager was available for any issues. We loved it and will try to stay...”
- Review left on 07/25/2016

$180

Excellent (14 reviews)

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from $180 / night

(1)

1 / 16

Clearwater House - 9 miles away

  • 2
  • 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Ask about children

$100

Excellent (1 reviews)

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from $100 / night

(3)

1 / 19

Clearwater House - 9 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Ask about children
“The neighborhood is very quiet and nice. The view from the deck is great providing an up close look of the birds and fish in the inlet and the more panoramic view of the Gulf straight ahead. It was also very pleasant to take our dog for walks...”
- Review left on 03/12/2017

$145

Very Good (3 reviews)

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from $145 / night

(20)

1 / 80

Clearwater Condo - 9.7 miles away

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“This condo was perfect. Close to everything, restaurants, grocery store and the Clearwater Ferry is about 2 miles away with free parking. It takes you right to the Clearwater Harbor which is right at Clearwater Beach. Nice 10 min. boat ride. The...”
- Review left on 08/13/2017

$83

Excellent (20 reviews)

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from $83 / night

1 / 10

Clearwater House - 9.9 miles away

  • 2
  • 4
  • 7 nights min
  • Ask about children
  • Pet friendly

$159

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from $159 / night

1 / 34

Clearwater House - 9.9 miles away

  • 5
  • 12
  • Min stay varies
  • Ask about children

$506

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from $506 / night

1 / 14

Clearwater House - 9.9 miles away

  • 2
  • 6
  • 1 night min
  • Ask about children

$357

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from $357 / night

1 / 17

Clearwater House - 9.9 miles away

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$450

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from $450 / night

(1)

1 / 21

Clearwater House - 9.9 miles away

  • 5
  • 15
  • Min stay varies
  • Swimming pool
  • Ask about children
“This site was excellent for a family reunion. Sleeping 13 was very comfortable. Site was clean, comfortable, nice pool, and 3 minutes to beach. Would highly recommended for a family gahering...”
- Review left on 08/15/2016

$535

Excellent (1 reviews)

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from $535 / night

(1)

1 / 10

Clearwater House - 9.9 miles away

  • 2
  • 6
  • Min stay varies
  • Ask about children
“We love to the place and it's very convenient , the owner are very friendly, helpful and so easy to excess to the beach. Talk about stuffs in the house anything I need they have it. The place a very quiet and very friendly surrounded people...”
- Review left on 06/28/2016

$171

Excellent (1 reviews)

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from $171 / night

1 / 4

Clearwater House - 9.9 miles away

  • 20
  • 50
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

$3500

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from $3500 / night

(1)

1 / 17

Clearwater House - 9.9 miles away

  • 3
  • 8
  • Min stay varies
  • Ask about children
“I have travelled al over the world, but this, by far, was my whole party's greatest experience. It was very easy to book, the place is stunning with amazing views, and the landlord is so sweet and accommodating . I highly recommend it and can't wait...”
- Review left on 06/28/2016

$325

Excellent (1 reviews)

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from $325 / night

1 / 26

Clearwater House - 10 miles away

  • 3
  • 10
  • Min stay varies
  • Ask about children

$325

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from $325 / night

(17)

1 / 32

Clearwater House - 10.2 miles away

  • 2
  • 5
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
“We felt like we were home. Everything was clean and tidy. The cottage is adorable with all its brightly coloured rooms. We loved having coffee on the front patio in the mornings and cocktails on the back patio in the evening. The neighborhood was...”
- Review left on 05/22/2016

$135

Excellent (17 reviews)

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from $135 / night

(6)

1 / 36

Clearwater House - 10.4 miles away

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“7 girlfriends spent s wwek celebrating our birthdays! We had everything possible at the house from cooking to relaxing. House is beautifully decorated; comfy beds; great pool and close enough to walk to beach. Great restaurants in Clesrwster and...”
- Review left on 11/06/2016

$457

Excellent (6 reviews)

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from $457 / night

(5)

1 / 10

Clearwater House - 10.5 miles away

  • 3
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Loved vacationing at the Margaritaville Pool home. The inside is soooo cute and decorated with beachy accents throughout. The kitchen is fully stocked with everything you need to cook with. We loved the screened porch and ate most of our meals there....”
- Review left on 10/03/2015

$325

Excellent (5 reviews)

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from $325 / night

(8)

1 / 30

Clearwater House - 10.5 miles away

  • 3
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We loved the property. Very clean and well maintained. The house is located in a well kept subdivision on the North Shore of Clearwater beach. It was a short walk to the beach, short distance to tourist attractions and still private enough to enjoy...”
- Review left on 07/19/2016

$249

Very Good (8 reviews)

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from $249 / night

(2)

1 / 8

Clearwater House - 10.5 miles away

  • 4
  • 12
  • Min stay varies
  • Ask about children
  • Air conditioning
“Great location, really is just steps from the beach. Nice quiet neighborhood. House is comfortable and well furnished. Worked well for our two families...”
- Review left on 01/02/2017

$475

Very Good (2 reviews)

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from $475 / night

1 / 12

Clearwater Condo - 10.6 miles away

  • 1
  • 4
  • 1 night min
  • Ask about children
  • Air conditioning

$135

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from $135 / night

1 / 8

Clearwater House - 10.6 miles away

  • 1
  • 4
  • 1 night min
  • Ask about children
  • Air conditioning

$135

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from $135 / night

(1)

1 / 34

Clearwater House - 10.6 miles away

  • 4
  • 8
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$415

Excellent (1 reviews)

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from $415 / night

1 / 49

Clearwater House - 10.6 miles away

  • 6
  • 22
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$529

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from $529 / night

1 / 16

Clearwater House - 10.6 miles away

  • 1
  • 4
  • Min stay varies
  • Ask about children

$214

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from $214 / night

(1)

1 / 19

Clearwater Condo - 10.6 miles away

  • 10
  • 30
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Coconut Grove was a fantastic location and experience. The sales, property management and maintenance staff were very accommodating and professional. The facility was very nice. There is an incredible bar, outside kitchen and swimming pool. Even...”
- Review left on 05/25/2016

$760

Excellent (1 reviews)

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from $760 / night

1 / 4

Clearwater Apartment - 10.6 miles away

  • 2
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$249

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from $249 / night

1 / 17

Clearwater Apartment - 10.6 miles away

  • 2
  • 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$159

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from $159 / night

(11)

1 / 54

Clearwater House - 10.7 miles away

  • 5
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“First of I would like to start by saying this was a wonderful stay for our family. The home is beautifully furnished and well equipped in the kitchen along with grill (BIG PLUS). After the beach the kids would bath in the pool while the family cooked...”
- Review left on 08/16/2016

$299

Very Good (11 reviews)

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from $299 / night

(11)

1 / 12

Tarpon Springs House - 10.7 miles away

  • 4
  • 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“Our family of 9 (8 adults and a one year old) spent a vacation week at the Tarpon Springs home and had a great time. The house is very clean and spacious, and is located in a beautiful quaint, quiet neighborhood. The master suite downstairs was very...”
- Review left on 10/04/2016

$230

Very Good (11 reviews)

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from $230 / night

1 / 16

Clearwater House - 10.7 miles away

  • 3
  • 8
  • 1 night min
  • Ask about children

$385

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from $385 / night