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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Compare 423 Cottages in Oldsmar with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (17)
"This property has every amenity you need for a comfortable stay. Inside and out, it was very clean and cozy. The host, Caleb, is amazing. His communication and responsiveness was excellent, even when we arrived very late. I highly recommend this property and will stay there again when I visit the area. "
Private Surf Shack Less Than 5 Minutes to Indian Rocks Beach Bikes Included!
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
Fridge, microwave, oven, stovetop

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!
BEACHFRONT COTTAGE! Step out the door and into the sand! On the Gulf of Mexico!!
Private beach, sun loungers, beach towels

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

9.8 out of 10, Exceptional, (206)
"Loved walking out the door and immediately hitting the sand. Quiet and lovely. "
The price is AED 1,083
AED 1,819 total
includes taxes & fees
28 Mar - 29 Mar
BEACHFRONT COTTAGE! Step out the door and into the sand! On the Gulf of Mexico!!
30 Second walk to the Beach. Newly Renovated-No Hurricane Damage. Free parking.
Outdoor dining

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

9.8 out of 10, Exceptional, (174)
"This property is just steps to the beach and conveniently located. Comfortable for the 2 of us. We would love to come back."
The price is AED 400
AED 882 total
includes taxes & fees
1 Apr - 2 Apr
30 Second walk to the Beach. Newly Renovated-No Hurricane Damage. Free parking.
Cozy Cottage - Close to Everything, Nature Lovers Dream!
Fridge, microwave, oven, stovetop

Cozy Cottage - Close to Everything, Nature Lovers Dream!

10.0 out of 10, Exceptional, (46)
"When we arrived at the property we were greeted by the owners, and their precious son along with a beautiful horse and mini horse. They left us fresh eggs from their chickens, and carrots to feed to horses. The inside of the home was immaculate, the decor was beautiful, very comfy feel and they had everything u may need to make your stay easy. Our furbabies enjoyed the fenced in yard as well. Very safe area in a country setting. We loved it. Absolutely recommend this place to anyone and we will...
The price is AED 584
AED 1,416 total
includes taxes & fees
22 Mar - 23 Mar
Cozy Cottage - Close to Everything, Nature Lovers Dream!
Bright, Clean and Cozy Coastal Cottage in Ozona
Outdoor dining

Bright, Clean and Cozy Coastal Cottage in Ozona

9.6 out of 10, Exceptional, (8)
"We stayed at the property for leisure and I also worked remotely. Was able to set my office in the kitchen. The host was very responsive. Great Location: we walked the Pinellas trail daily and Tarpon Tom's bike rental is 5 min walk from this rental. "
The price is AED 613
AED 1,278 total
includes taxes & fees
6 Mar - 7 Mar
Bright, Clean and Cozy Coastal Cottage in Ozona
Riverside Casita: semi-private pool, spa, dock, garden oasis, 5 min to downtown!
Beach towels

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

10.0 out of 10, Exceptional, (60)
"Very nice. Quiet we enjoyed our stay"
Riverside Casita: semi-private pool, spa, dock, garden oasis, 5 min to downtown!
Old world Florida cottage
Miscellaneous

Old world Florida cottage

9.6 out of 10, Exceptional, (14)
"This place was just what I was looking for small and comfortable, but had all the conveniences coffee maker, microwave, etc. loved it. It was also nice and clean and close to the bike trail, which was awesome."
Old world Florida cottage
Frenchy's Cottage 482 in Clearwater Beach
Aerial view

Frenchy's Cottage 482 in Clearwater Beach

10.0 out of 10, Exceptional, (11)
"My family (3 adult couples) stayed in this property to attend a wedding. Very clean and new! We loved having coffee on the back patio. Very walkable to the beach and restaurants - dinner, coffee shops, bars! Beach chair rental place right on the beach was convenient. Would love to come back!!"
Frenchy's Cottage 482 in Clearwater Beach
Frenchy's Cottage 486 in Clearwater Beach
Aerial view

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
Charming cottage in old Florida Odessa lake community with AC, WiFi, kayak
Exterior

Charming cottage in old Florida Odessa lake community with AC, WiFi, kayak

9.4 out of 10, Exceptional, (3)
"It was great. Wonderful accommodations and location."
Charming cottage in old Florida Odessa lake community with AC, WiFi, kayak
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
Beach nearby, sun loungers, beach towels

Sleeps 6 Daily Rentals, Pets OK, Hot Tub

8.8 out of 10, Excellent, (48)
"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 1,686
AED 2,847 total
includes taxes & fees
4 Mar - 5 Mar
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
Historic Beach Cottage steps from beach. Pet friendly!
On the beach, sun loungers, beach towels

Historic Beach Cottage steps from beach. Pet friendly!

9.2 out of 10, Wonderful, (116)
"The place was exactly as advertised. It needs a little love but the location is excellent and the staff very nice. The weather didn't cooperate so I didn't have the opportunity to enjoy the property as much as I would have liked. . Cap Al has lots of beach items, chairs, beach towels for your use. Once again the location is excellent for beach walks and sunsets. It is walking distance to everything. I enjoyed my visit . Thank you "
The price is AED 1,355
AED 2,426 total
includes taxes & fees
18 Mar - 19 Mar
Historic Beach Cottage steps from beach. Pet friendly!
Downtown Dunedin Cottage Near Beaches + Breweries
Beach

Downtown Dunedin Cottage Near Beaches + Breweries

10.0 out of 10, Exceptional, (51)
"Everything was perfect. Great little place with a good location."
Downtown Dunedin Cottage Near Beaches + Breweries
Private family waterfront beach cottage. Best location step out to bay and gulf
On the beach

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

9.0 out of 10, Wonderful, (81)
"Very cute and quaint quite cottage "
The price is AED 1,099
AED 2,079 total
includes taxes & fees
4 Mar - 5 Mar
Private family waterfront beach cottage. Best location step out to bay and gulf
Private Studio Just two block to Lassing park waterfront
Aerial view

Private Studio Just two block to Lassing park waterfront

10.0 out of 10, Exceptional, (34)
"Had a very comfortable leg stay for a week long work trip. The cottage had everything I need to cook a bit. The bed and bedding were insanely comfy. Getting there and checking in were a breeze. "
Private Studio Just two block to Lassing park waterfront
Tropical Coquina Cove Studio #5 Heated POOL. 5 Min Walk to Beach
A heated pool

Tropical Coquina Cove Studio #5 Heated POOL. 5 Min Walk to Beach

9.6 out of 10, Exceptional, (11)
"Lovely, tropical, and serene. Very relaxing. Just disappointed that local channels/TV were not available. Yes, had roku TV however, local channels weren't available. i.e. unable to watch the grammys this past weekend, nor morning local news, wheel of fortune or jeopardy in the evenings. If want to watch super bowl this weekend you won't be able to, unless you have a way to get Fox channel yourself. When inquired to get, was informed that booking description did not say provide local...
Tropical Coquina Cove Studio #5 Heated POOL. 5 Min Walk to Beach
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
Beach nearby, sun loungers, beach towels

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!
Perfect Cottage In Art District of Gulfport
Property grounds

Perfect Cottage In Art District of Gulfport

9.6 out of 10, Exceptional, (88)
"The house was clean, sweetly decorated, and located perfectly for enjoying downtown Gulfport. We had everything we needed, and loved our stay! Thank you!"
Perfect Cottage In Art District of Gulfport
Close to Sponge docks,private separate entrance, in the heart of Tarpon Spring!
Terrace/patio

Close to Sponge docks,private separate entrance, in the heart of Tarpon Spring!

9.0 out of 10, Wonderful, (2)
"Good "
Close to Sponge docks,private separate entrance, in the heart of Tarpon Spring!
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
Beach nearby, beach volleyball, fishing

Sailport Waterfront Suites

3.5 star property
8.4 out of 10, Very Good, (4410)
"This is my go to for my vacations, quick midweek/weekend get away. I love that it's close to fishing spots, grocery, entertainment. Only thing, they need to made thst elevator move faster 😂 "
The price is AED 723
AED 879 total
includes taxes & fees
3 Apr - 4 Apr
Sailport Waterfront Suites
Chase Suite Hotel Rocky Point Tampa
Front of property

Chase Suite Hotel Rocky Point Tampa

3.0 star property
7.6 out of 10, Good, (4834)
"Very very peaceful. Hotel was more like a apartment. Stove and fridge as well as utensils and plates. Staff was very nice "
The price is AED 650
AED 731 total
includes taxes & fees
4 Mar - 5 Mar
Chase Suite Hotel Rocky Point Tampa
Sunset Vistas Two Bedroom Beachfront Suites
2 outdoor pools, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers

Sunset Vistas Two Bedroom Beachfront Suites

3.5 star property
8.8 out of 10, Excellent, (3161)
"Nice beach access large rooms and nice pool areas"
The price is AED 1,209
AED 1,458 total
includes taxes & fees
4 Mar - 5 Mar
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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