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Compare 472 Cottages in Oldsmar with updated reviews, rates, and availability.

Property grounds
Brand New! 30 Second walk to the Beach. PRIVATE & PERFECT FOR SOCIAL DISTANCING
9.8 out of 10, Exceptional, (147)
"This cozy little beach cottage is clean and well maintained and in the perfect location, just a few steps from the beach. It’s also just a short walk to downtown Clearwater Beach where you can find plenty of shops and restaurants. The owners provide everything needed for a beach vacation for two! We look forward to staying here again."
Brand New! 30 Second walk to the Beach. PRIVATE & PERFECT FOR SOCIAL DISTANCING
Exterior
Turquoise Shores Cozy Cottage Near the Beach!
9.8 out of 10, Exceptional, (47)
"Turquoise Shores was a perfect place to stay for a relaxing getaway. The size was perfect for the 2 of us. We loved sitting at the outdoor table in the mornings with our coffee. The beach was only across the street which was very convenient. There was also some great beach bars close by within walking distance. Ann was great and took care of anything that was needed and gave us some great material of the area. We will definitely be staying here again."
Turquoise Shores Cozy Cottage Near the Beach!
On the beach, sun loungers, beach towels
BEACHFRONT COTTAGE! On the Gulf of Mexico! Groundfloor! Direct OCEANFRONT!
9.8 out of 10, Exceptional, (194)
"loved our stay here. right on the beach. cozy and clean! owner very communicative. will definitely be back"
BEACHFRONT COTTAGE! On the Gulf of Mexico! Groundfloor! Direct OCEANFRONT!
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Snow and ski sports
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
9.0 out of 10, Wonderful, (38)
"The old Florida cottage was old Florida. It was clean with history and very friendly property management. I grew up in this area and this is what vacation was before all the resorts cluttered the beach. I mis booked our cottage and the manager met me and fixed it without argument. Close to the beach and far enough from south beach that you had some peaceful time off. Would definitely go back and have already recommended to several friends and family."
The price is $189
$432 total
includes taxes & fees
May 28 - May 29
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
Fridge, microwave, oven, stovetop
BRAND NEW! Cozy Bungalow - Steps to the Beach- Perfect for Social Distancing.
10.0 out of 10, Exceptional, (119)
"We have been in this area for 5 years renting. Unable to rent our usual place do to ? changes in ownership. The rental was perfect for beach access, that’s why we rent this area. The bungalow needs a full length mirror, more beach decorations. Overall a great stay."
BRAND NEW! Cozy Bungalow - Steps to the Beach- Perfect for Social Distancing.
Terrace/patio
Cottage by the gulf
10.0 out of 10, Exceptional, (24)
"When we arrived at the property I was given earlier the door combo so we were able to get in. It was very clean and inviting as you walked thru the door. The Kitchen was a gallery and a bit small but very nice and well equipped. We were impressed as a basket of snacks and some waters were on the counter for our use. We were never given snacks and it gave us a good feeling that our hostess cares and is very thoughtful. The area was quiet but we couldn't get much to watch on the TV."
Cottage by the gulf
1 bedroom, free WiFi, bed sheets
****Tropical Coquina Cove Studio #3 Heated POOL . 5 Min walk to Beach ****
9.8 out of 10, Exceptional, (13)
"Great location, around the corner from beach in a quiet neighborhood. Owner was very responsive, would stay again."
****Tropical Coquina Cove Studio #3 Heated POOL . 5 Min walk to Beach ****
Exterior
COZY COTTAGE ON PRIVATE BEACH *CLEARWATER/BELLEAIR BEACH
9.6 out of 10, Exceptional, (40)
"Stayed here for Spring Break 24' and had a very relaxing stay! Beach is a close walk from the backdoor, the cottage location is not far from great amenities (ice cream, coffee, small shops). Already booked again for Spring Break 25'!"
COZY COTTAGE ON PRIVATE BEACH *CLEARWATER/BELLEAIR BEACH
Outdoor pool, a heated pool
BANANA BREEZE COTTAGE. Steps away from the beach Heated pool.
10.0 out of 10, Exceptional, (44)
"This cottage is wonderfully located on Clearwater Beach. Near restaurants and shopping. There is a wonderful state park near by. The grounds are nicely landscaped, very quiet and an easy place to sit and read."
BANANA BREEZE COTTAGE. Steps away from the beach Heated pool.
Outdoor pool, a heated pool
The Lazy Lemon Cottage Steps From the Beach, Frenchys and Palm Pavilion.
10.0 out of 10, Exceptional, (101)
"The Lazy Lemon cottage is comfortable and centrally located. Easy walk to the beach, restaurants and shopping. Our host, James, was very responsive. We enjoyed our time so much that we stayed an extra day!"
The Lazy Lemon Cottage Steps From the Beach, Frenchys and Palm Pavilion.
Beach
Private Studio Just two block to Lassing park waterfront
10.0 out of 10, Exceptional, (25)
"Checkin was smooth. Tom left us a bottle of wine to enjoy. Very modern , clean, and complete with everything you need for a great stay. Love the details in everything. Crisp Ralph Lauren sheets and Tommy Bahamma bedspread."
Private Studio Just two block to Lassing park waterfront
Fridge, microwave, oven, stovetop
Cheerful Clearwater Cottage - 2 Bedroom & Parking
8.6 out of 10, Excellent, (11)
"I’m so glad that I found this place for my family! Everything was clean and neat when we walked in which was very nice. Beds were comfortable and both rooms were very spacious. It was great being minutes away from Clearwater beach as well! So if you’re looking for a rental that’s kid friendly, this one is it! Easy communication with owners too, response time was quick and helpful. Thank you so much for letting my family stay :)"
Cheerful Clearwater Cottage - 2 Bedroom & Parking
Outdoor pool, a heated pool
ORANGE BLOSSOM COTTAGE two minute Walk to Beach
9.8 out of 10, Exceptional, (69)
"We really enjoyed our stay at Orange Blossom. Great communication and quick solutions to any questions or concerns. James was very informative and gave some great suggestions to surrounding area."
ORANGE BLOSSOM COTTAGE two minute Walk to Beach
Aerial view
Frenchy's Cottage 480 in Clearwater Beach
9.6 out of 10, Exceptional, (16)
"We were in town for a family wedding. We loved the location. It was a great place for our family with direct access to the beach and all the restaurants nearby. We highly recommend this cottage to anyone looking to visit Clearwater Beach."
Frenchy's Cottage 480 in Clearwater Beach
Beach
A 2 BR, 2 BA Downstairs Unit right across the street from John's Pass Village!
9.6 out of 10, Exceptional, (122)
"The beach was close to the cottage & the water was awesome! The cottage had a great patio to sit and have coffee and a supply of beach gear including canopies & some chairs… the kitchen was spacious & each bedroom had a bathroom - great place for a vacation- close to the pass ."
A 2 BR, 2 BA Downstairs Unit right across the street from John's Pass Village!
Beach nearby
New Listing Sunset Tropical Beach Bungallow
9.8 out of 10, Exceptional, (24)
"The rental was very nice. Communication with the owner and property manager was excellent. We enjoyed the accommodation as they met our expectations fully. We would recommend this property to others."
The price is $163
$382 total
includes taxes & fees
May 31 - Jun 1
New Listing Sunset Tropical Beach Bungallow
Property grounds
Bright, Clean and Cozy Coastal Cottage in Ozona
8.0 out of 10, Very Good, (1)
"We were very comfortable in this clean and comfortable house. Everything worked well. Beds comfortable. We had extra family stay a few nights and they were comfy too. It’s walking and central to Ozona and Palm Harbor restaurants. Bike path in back yard. Starchans ice cream at the end of street. The location is directly accross from USPS so there was to be expected occasional noise. Nothing that kept us awake."
Bright, Clean and Cozy Coastal Cottage in Ozona
Living area | TV, DVD player
Yachtsman*OCEAN FRONT COTTAGE*Right on the sand*sleeps up to 6*Heated Pool
9.8 out of 10, Exceptional, (51)
"The cottage was my perfect for my family of 4. You can’t ask for a better view or location."
Yachtsman*OCEAN FRONT COTTAGE*Right on the sand*sleeps up to 6*Heated Pool
Property grounds
Best deal on the beach/sleeps 6/All New/Gulf views!/55 inch TV
9.8 out of 10, Exceptional, (174)
"We enjoy the perfect location across from the Gulf. Wonderful pool by the causeway. Great low key atmosphere."
Best deal on the beach/sleeps 6/All New/Gulf views!/55 inch TV
Lake
Treasure Island Cottage, Near Boardwalk & Beach!
9.4 out of 10, Exceptional, (25)
"The size of the place was perfect. They had everything we needed. Was a nice neighborhood. Stores and restaurants were very close."
Treasure Island Cottage, Near Boardwalk & Beach!
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See all available properties in Oldsmar
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Oldsmar

Beach nearby, beach volleyball, fishing
Sailport Waterfront Suites
3.5 star property
8.4 out of 10, Very Good, (4123)
"Great view, nice room, great location."
The price is $152
$191 total
includes taxes & fees
May 27 - May 28
Sailport Waterfront Suites
Front of property
Chase Suite Hotel Rocky Point Tampa
3.0 star property
7.6 out of 10, Good, (4279)
"Love it"
The price is $109
$124 total
includes taxes & fees
Jun 20 - Jun 21
Chase Suite Hotel Rocky Point Tampa
Studio (with Common Living Area (B)) | Premium bedding, in-room safe, individually decorated
ROOST Tampa
5.0 star property
9.4 out of 10, Exceptional, (298)
"Awesome short stay apartment with updated appliances. Beautiful pool. Very dog friendly."
The price is $169
$192 total
includes taxes & fees
May 27 - May 28
ROOST Tampa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oldsmar Cottages information

Number of reviews
1,110
Accommodation
472 Cottages
Lowest Price
$163
Highest Price
$189

Frequently asked questions

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What is there to do in Oldsmar near my cottage?
Oldsmar has enough experiences to keep you busy for weeks (or months!), starting with Ben T. Davis Beach. Big Cat Rescue, Oldsmar Historical Society Museum and Westchase Golf Course are other fantastic attractions. If you have time to spare, Oldsmar Flea Market and Rocky Point Golf Course are nice final touches to your itinerary.

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