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Compare 455 Cottages in Oldsmar with updated reviews, rates, and availability.

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

9.8 out of 10, Exceptional, (164)
"This property was great, i would definitely stay again."
30 Second walk to the Beach. Newly Renovated-No Hurricane Damage. Free parking.

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

10.0 out of 10, Exceptional, (50)
"We arrived at the "casita" after nine pm. We opened the gate to find the prettiest little pool area and place to stay. What a wonderful surprise ! Warm, twinkling lights amid florida foliage created such a welcoming atmosphere. We felt at home immediately. Heather and Tim are terrific hosts. They went above and beyond anything that was asked of them. Everything was clean and neat. A perfect size for the two of us. If we come back this way,this is where we'll stay."
Riverside Casita: semi-private pool, spa, dock, garden oasis, 5 min to downtown!

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

9.6 out of 10, Exceptional, (13)
"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

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

COCONUT CABANA Heated Pool, two minutes walk to Beach.

9.8 out of 10, Exceptional, (101)
"Very nice little spot. Walked from there to most everything. Very enjoyable "
COCONUT CABANA Heated Pool, two minutes walk to Beach.

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

Old world Florida cottage

9.8 out of 10, Exceptional, (9)
"Very clean and close to the ocean (3 min walk) and the quaint town of Dunedin -10 minute walk. Some lovely restaurants in town including the Fish Camp , Cafe Alfresco and Wild Iris cafe (breakfast). The town is recovering from Hurricane Milton and welcomes all tourists. This rental did not appear affected by the hurricane. Worth noting that the unit is a good size for 1 propane but the bed is a little cramped especially if you are tall or broad. "
Old world Florida cottage

Quaint bungalow just off Main Street

9.4 out of 10, Exceptional, (23)
"We booked this house for a month long stay. It could not have been a more perfect location for us. It is literally around the corner from the main street restaurants, bars and shops. We walked everywhere. The house was nicely remodeled. Fresh paint and sea side decor. The kitchen was well stocked with everything we needed - except groceries. The air conditioning worked great and the king bed was very comfy. The front porch was nice for evening drinks and relaxation. In the back is a huge deck...
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

Shotgun Style in the Heart of Historic Ybor

10.0 out of 10, Exceptional, (22)
"Really nice property. Very quaint. "
Shotgun Style in the Heart of Historic Ybor

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

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!

Perfect Cottage In Art District of Gulfport

9.6 out of 10, Exceptional, (85)
"We just love this cottage in the heart of Gulfport. Fully furnished with amazing amenities. Highly recommend a stay!"
Perfect Cottage In Art District of Gulfport

White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!

9.6 out of 10, Exceptional, (100)
"This was our 2nd time staying at the Egret cottage and we had a lovely stay. House is just as it’s pictured. Clean and comfortable. The location is great. Close to the beach yet away from the crowds."
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!

Cozy Cottage - Close to Everything, Nature Lovers Dream!

10.0 out of 10, Exceptional, (39)
"Nice place. Just a few nits. Ran out of hot water after 5 mins. Toilet in one bath was unstable. "
The price is AED 584
AED 1,194 total
includes taxes & fees
6 Dec - 7 Dec
Cozy Cottage - Close to Everything, Nature Lovers Dream!

Beachside Historic Cottage Apartment – Steps to Sand

Beachside Historic Cottage Apartment – Steps to Sand

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

10.0 out of 10, Exceptional, (9)
"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!

Downtown Dunedin Cottage Near Beaches + Breweries

10.0 out of 10, Exceptional, (43)
"Small, but very clean and quite. Hubby in hospital at meise so location was Greater "
Downtown Dunedin Cottage Near Beaches + Breweries

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

Sleeps 6 Daily Rentals, Pets OK, Hot Tub

9.0 out of 10, Wonderful, (46)
"Cozy spot in the perfect location! This place is ideal for a laid back beach vaca. Kids loved it, felt very safe and everything we needed was in walking distance. Great community outdoor space with hot tub and dining area. Captain Al is a fantastic host! Thank you!!"
The price is AED 584
AED 1,444 total
includes taxes & fees
1 Dec - 2 Dec
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
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

Chase Suite Hotel Rocky Point Tampa

3.0 star property
7.6 out of 10, Good, (4618)
"I love the way the treat you . Very clean "
The price is AED 485
AED 550 total
includes taxes & fees
28 Nov - 29 Nov
Chase Suite Hotel Rocky Point Tampa

Sailport Waterfront Suites

3.5 star property
8.4 out of 10, Very Good, (4321)
"I️ had to find a last minute place to stay. I️ called with some questions, they were answered quickly and accurately, booked my night. Check in was super easy and fast. I️ was in my room in less than 5 minutes. The room was clean and beautiful! I️ was surprised with a complimentary bottle of wine! Had a bite to eat at the tiki bar, food was great. Bed comfortable! I️ was exhausted from my trip and they were able to provide me with a complimentary late check out! I️ highly recommend! My next trip...
The price is AED 469
AED 605 total
includes taxes & fees
8 Dec - 9 Dec
Sailport Waterfront Suites

Sunset Vistas Two Bedroom Beachfront Suites

3.5 star property
8.8 out of 10, Excellent, (3100)
"We went to the resort about a month after the hurricane and expected the place to be in worse shape than it was. The resort is on a beautiful piece of ocean front property and would definitely come here again. It is a little out dated and our room smelled of stale cigarettes. Other than those 2 things we had a fantastic time on the beach for 2 days"
The price is AED 604
AED 768 total
includes taxes & fees
18 Dec - 19 Dec
Sunset Vistas Two Bedroom Beachfront Suites
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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