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Compare 431 Cottages in Oldsmar with updated reviews, rates, and availability.

★Getaway!★Stocked+2Bikes★beach just short drive away ★WorkfromHome

9.0 out of 10, Wonderful, (14)
"We were in town for a swim meet at the north shore aquatic complex and this house was the perfect location. We could get to warm up at 7am in 10 mins tops and walk down and back when schedule permitted. It’s also close to amazing restaurants and the neighborhood was perfect for our dog! The house is super close to Crescent Lake, which is lovely - a path, pickleball and a dog park are all there. Will definitely return if we find ourselves back in St Pete. And to top that all off, Lisa is a GREAT...
★Getaway!★Stocked+2Bikes★beach just short drive away ★WorkfromHome

Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!

10.0 out of 10, Exceptional, (127)
"Great stay and close to the sugar sand beach. Mary our host was great. I would recommend staying there."
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!

Private Surf Shack Less Than 5 Minutes to Indian Rocks Beach Bikes Included!

10.0 out of 10, Exceptional, (12)
"We loved it and hope to stay there every year for our family! So clean and Caleb has thought of everything one could possibly need!! Thanks so much!!!"
Private Surf Shack Less Than 5 Minutes to Indian Rocks Beach Bikes Included!

Best deal on the beach/sleeps 6/All New/Gulf views!/55 inch TV

9.8 out of 10, Exceptional, (180)
"We had a great time at this property. It was right across from a great family beach and close to drive to everything."
Best deal on the beach/sleeps 6/All New/Gulf views!/55 inch TV

Riverside Casita: semi-private pool, spa, dock, garden oasis, 5 min to downtown!

10.0 out of 10, Exceptional, (53)
"This property is in a great location for visiting the Tampa Area. The hosts were very nice. The property is very tropical, and has a great pool and hot tub. We would stay here again."
Riverside Casita: semi-private pool, spa, dock, garden oasis, 5 min to downtown!

30 Second walk to the Beach. Newly Renovated-No Hurricane Damage. Free parking.

9.8 out of 10, Exceptional, (165)
"Our stay was great! The host let us checkout late since we had a later flight. Location was fantastic! Just steps from the beach!! All appliances are newer and the kitchen included plates, bowls, coffee cups, toaster, blender, etc! There were beach towels to use, as well as beach chairs, an umbrella, a cooler. Additionally, there was grill to use - which is how we made our Thanksgiving meal there was construction right next door, but did not impact our stay one bit. "
30 Second walk to the Beach. Newly Renovated-No Hurricane Damage. Free parking.

BEACHFRONT COTTAGE! Step out the door and into the sand! On the Gulf of Mexico!!

9.8 out of 10, Exceptional, (205)
"This is a wonderful place right on the Gulf, hid away from all the noise and could hear the ocean practically all day."
The price is AED 918
AED 1,614 total
includes taxes & fees
2 Jan - 3 January 2025
BEACHFRONT COTTAGE! Step out the door and into the sand! On the Gulf of Mexico!!

Private Studio Just two block to Lassing park waterfront

10.0 out of 10, Exceptional, (30)
"The studio apartment was very cute and more than functional. I had family in the neighborhood so I mostly just slept there but I could have cooked, the kitchen was well stocked. The only thing I missed was I would have liked to use a washing machine but there wasn’t one in the little house. "
Private Studio Just two block to Lassing park waterfront

Frenchy's Cottage 486 in Clearwater Beach

9.2 out of 10, Wonderful, (15)
"Awesome stay walking distance to everything in Clearwater including beach and Hulk Hogans bar"
Frenchy's Cottage 486 in Clearwater Beach

Clearwater Cottage - 2 BR / 1 Bath

8.8 out of 10, Excellent, (13)
"Enjoyed our stay. The house is in a convenient location and very easy to get to. The owners were accommodating to our needs. The neighborhood is quiet and safe. I would recommend for small groups."
Clearwater Cottage - 2 BR / 1 Bath

Quaint bungalow just off Main Street

9.4 out of 10, Exceptional, (24)
"great location close to all of town walk to every thing "
Quaint bungalow just off Main Street

The Sunshine Cottage. Walk To Beach, Shops, Dining & Water Sports

10.0 out of 10, Exceptional, (104)
"Judy has thought of everything- lovely furniture and decor; close enough to the beach but far enough from the crowds; all the dishes you could use; top quality towels; the pool; bikes and beach equipment are a plus. Our second time staying here, will stay again."
The Sunshine Cottage. Walk To Beach, Shops, Dining & Water Sports

Yachtsman*OCEAN FRONT COTTAGE*Right on the sand*sleeps up to 6*Heated Pool

9.8 out of 10, Exceptional, (52)
"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

Private family waterfront beach cottage. Best location step out to bay and gulf

9.0 out of 10, Wonderful, (75)
"Quaint little bungalow footsteps from the beach! Location was perfect! It’s not fancy, and like others have stated, it could use a “refresh” on some of the furniture / paint, however, it was clean and all functional. If you like a low key location with a very quiet beach, you are laid back, and don’t need fancy furnishings/decor , then this place is perfect! Would absolutely stay here again. "
The price is AED 498
AED 1,370 total
includes taxes & fees
1 Jan - 2 January 2025
Private family waterfront beach cottage. Best location step out to bay and gulf

Cozy Cottage in the Heart of Dunedin

10.0 out of 10, Exceptional, (7)
"Excellent place to stay. Off-street parking walking distance to downtown and bike path and central to the rest of Dunedin."
The price is AED 360
AED 951 total
includes taxes & fees
3 Jan - 4 January 2025
Cozy Cottage in the Heart of Dunedin

5 Mi to Beach: Family-friendly Home in Clearwater!

3.0 star property
10.0 out of 10, Exceptional, (1)
5 Mi to Beach: Family-friendly Home in Clearwater!

Downtown Dunedin Cottage Near Beaches + Breweries

10.0 out of 10, Exceptional, (46)
"Very clean and conveniently located for a short stay in downtown Dunedin. Close enough to walk and far enough away from town to avoid the noise from the bars. short walk to the pinellas trail and restaurants/bars of Dunedin"
Downtown Dunedin Cottage Near Beaches + Breweries

Waterfront Cottage with a dock

9.8 out of 10, Exceptional, (11)
"Cute trailer , supplied with everything we needed "
Waterfront Cottage with a dock

Breathtaking Lake View Cottage

10.0 out of 10, Exceptional, (1)
"Great stay and great host "
The price is AED 547
AED 1,021 total
includes taxes & fees
3 Jan - 4 January 2025
Breathtaking Lake View Cottage

3 Mi to Busch Gardens - Vacation Rental in Tampa

3.0 star property
10.0 out of 10, Exceptional, (1)
"We loved the house, everything was clean and organize. We love the patio and had so much fun playing with the mini golf. "
3 Mi to Busch Gardens - Vacation Rental in 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.
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Other property types in Oldsmar

Sailport Waterfront Suites

3.5 star property
8.4 out of 10, Very Good, (4348)
"Everything was great only downfall only one elevator worked! Everything else great! Will return again!"
The price is AED 521
AED 652 total
includes taxes & fees
12 Jan - 13 January 2025
Sailport Waterfront Suites

Chase Suite Hotel Rocky Point Tampa

3.0 star property
7.6 out of 10, Good, (4670)
"The property is a bit older and it shows."
The price is AED 525
AED 591 total
includes taxes & fees
1 Jan - 2 January 2025
Chase Suite Hotel Rocky Point Tampa

Mint House St. Petersburg - Downtown

4.5 star property
9.4 out of 10, Exceptional, (525)
"Everyone is so nice there. Rooms are nice and big."
The price is AED 595
AED 672 total
includes taxes & fees
26 Jan - 27 January 2025
Mint House St. Petersburg - Downtown
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.

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