Search Oldsmar Cottage Rentals from CA $127

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Oldsmar Cottages

The Purple Flower - 30 Second walk to the Beach. Free parking.
Outdoor dining

The Purple Flower - 30 Second walk to the Beach. Free parking.

9.8 out of 10, Exceptional, (189)
"Very smooth process the whole way through. Very clean and cozy stay. Loved that we could get up and walk straight to the beach. Driveway parking was a bonus! "
The price is CA $212
CA $416 total
includes taxes & fees
Aug 18 - Aug 19
The Purple Flower - 30 Second walk to the Beach. Free parking.
Perfect Cottage In Art District of Gulfport
Fridge, microwave, oven, stovetop

Perfect Cottage In Art District of Gulfport

9.6 out of 10, Exceptional, (94)
"Very Clean and plenty of room for 2."
Perfect Cottage In Art District of Gulfport
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, (92)
"This was the most lovely rustic little beach house. Just perfect. I’d live here. "
Private family waterfront beach cottage. Best location step out to bay and gulf
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, (109)
"Great location and amenities! The place was cozy and the short walk to the beach was amazing. The bed was a little stiff and was a little warm being on the upper floor of the house but still a great stay overall!"
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
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, (61)
"The little touches made this stay great perfect for people traveling with a dog very dog friendly"
The price is CA $197
CA $500 total
includes taxes & fees
Aug 12 - Aug 13
Cozy Cottage - Close to Everything, Nature Lovers Dream!
The Flip Flop Waterfront Beach Retreat - Close to Beaches
Smart TV

The Flip Flop Waterfront Beach Retreat - Close to Beaches

10.0 out of 10, Exceptional, (1)
"Loved our stay, super cute house! Very clean, beds were comfortable. We fished in the pond at the back of the property and caught a few fish! The T.V. doesn't work good, but internet was great. Very close to honeymoon island beach and beautiful park at the end of the road you can walk to and watch the sun set. Local restaurants are great and a dunkin right around the corner. Very quiet neighborhood. We'll definitely come back. "
The price is CA $127
CA $295 total
includes taxes & fees
Aug 10 - Aug 11
The Flip Flop Waterfront Beach Retreat - Close to Beaches
Two-bedroom bungalow - Old FL Cottage - Gulf Side - Ground Level
Beach nearby, sun loungers, beach towels

Two-bedroom bungalow - Old FL Cottage - Gulf Side - Ground Level

10.0 out of 10, Exceptional, (28)
"One of our favorite places to stay"
Two-bedroom bungalow - Old FL Cottage - Gulf Side - Ground Level
The Seaside Cottages are located just across the street from Indian Rocks Beach!
Outdoor dining

The Seaside Cottages are located just across the street from Indian Rocks Beach!

9.6 out of 10, Exceptional, (9)
"This cottage was the perfect place for relaxing and enjoying the beach, as well as visiting friends and family in Tampa."
The Seaside Cottages are located just across the street from Indian Rocks Beach!
Downtown Dunedin Keylime Cottages 4, right in Downtown Dunedin
Sun loungers, beach towels

Downtown Dunedin Keylime Cottages 4, right in Downtown Dunedin

10.0 out of 10, Exceptional, (30)
"Great experience!! Will definitely stay there again!"
Downtown Dunedin Keylime Cottages 4, right in Downtown Dunedin
Canary Beach Cottage - steps to the sand!
Exterior

Canary Beach Cottage - steps to the sand!

9.6 out of 10, Exceptional, (45)
"Cute cottage in a great location for our beach getaway. Great staff and place was perfect. Would stay again. "
Canary Beach Cottage - steps to the sand!
Downtown Dunedin Cottage Near Beaches + Breweries
Beach

Downtown Dunedin Cottage Near Beaches + Breweries

10.0 out of 10, Exceptional, (67)
"Great cottage. Very clean and property Manager was great. Location to downtown bars and breweries was awesome. Would definitely stay there in the future. "
Downtown Dunedin Cottage Near Beaches + Breweries
100 Steps to Beach. Pets Ok, Real Beach House, Daily Rentals
Beach nearby, sun loungers, beach towels

100 Steps to Beach. Pets Ok, Real Beach House, Daily Rentals

9.0 out of 10, Wonderful, (76)
"Cute quiet place Fair price and close to beach and restaurants. Would stay again"
The price is CA $255
CA $845 total
includes taxes & fees
Aug 11 - Aug 12
100 Steps to Beach. Pets Ok, Real Beach House, Daily Rentals
Beachside Historic Cottage – Steps to Sand!
On the beach, sun loungers, beach towels

Beachside Historic Cottage – Steps to Sand!

10.0 out of 10, Exceptional, (13)
"Great location. Beautiful beach. I’d like to visit again "
Beachside Historic Cottage – Steps to Sand!
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, (120)
"We LOVED staying at Capt. Al's corner cottage. It was such a cute place and perfect for what we were looking for. Walking distance to everything, steps away from the beach and so relaxing! We especially loved the hot tub that was just out the back door and the atmosphere was so "beachy"....5 stars is not enough for this little gem of a place!"
The price is CA $184
CA $484 total
includes taxes & fees
Aug 10 - Aug 11
Historic Beach Cottage steps from beach. Pet friendly!
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!

9.8 out of 10, Exceptional, (142)
"Location and house were great! Adorable house close to beach! Exactly what we needed!!"
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, (214)
"My wife & I totally enjoyed our stay in Linda’s little bungalow on the ocean. Perfect beach location."
The price is CA $344
CA $609 total
includes taxes & fees
Aug 13 - Aug 14
BEACHFRONT COTTAGE! Step out the door and into the sand! On the Gulf of Mexico!!
Island Vibes Cottage | Amazing Location
Beach nearby

Island Vibes Cottage | Amazing Location

9.0 out of 10, Wonderful, (35)
"We had a beautiful stay in Clearwater. The cottage was perfect for two and great walk to the beach as well as downtown. Great food everywhere we turned! We will be back!"
Island Vibes Cottage | Amazing Location
Beachfront Cottages (Patio) at Beautiful Sandy Shores on Gulf of Mexico
Property grounds

Beachfront Cottages (Patio) at Beautiful Sandy Shores on Gulf of Mexico

10.0 out of 10, Exceptional, (159)
"Sandy Shores was a perfect place to soak up the sun and enjoy a balance of peace and quiet and activities. The Patio Cottage was clean and comfortable with all the amenities we needed. A king size bed, cable tv, internet, kitchen, bath, grill, patio and right next to the beach. Good restaurants within walking distance. Our hostess, Myrtle responded to emails and texts and really made us feel welcome. Our area did not feel overly commercial and had a nice neighborhood feel. It was great and we...
Beachfront Cottages (Patio) at Beautiful Sandy Shores on Gulf of Mexico
“A” Beachy Keen Cottage! Just Steps From Indian Rocks Beach!
Beach nearby, sun loungers, beach towels

“A” Beachy Keen Cottage! Just Steps From Indian Rocks Beach!

9.8 out of 10, Exceptional, (55)
"Great location! One block from beach. Host provided all the beach necessities including chairs, towels, umbrellas, coolers, & boogie boards. Walking distance to restaurants, bars, coffee shops & ice cream. And then you can relax at night in the hot tub. We loved our stay!"
“A” Beachy Keen Cottage! Just Steps From Indian Rocks Beach!
A 2 BR, 2 BA Downstairs Unit right across the street from John's Pass Village!
Beach

A 2 BR, 2 BA Downstairs Unit right across the street from John's Pass Village!

9.6 out of 10, Exceptional, (129)
"We have stayed here two years in a row and love it every time"
A 2 BR, 2 BA Downstairs Unit right across the street from John's Pass Village!
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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Top Oldsmar Hotel Reviews

Grand Hyatt Tampa Bay

Grand Hyatt Tampa Bay

10/10 Excellent
"The place is lovely and the staff was very helpful especially the guys at entrance. Accessibility was not pleasant. The downside of our stay: requested bay view didn’t get and reservations made well in advance, the AC unit was faulty and noisy and the sink slow to empty probably needed a cleaning. Otherwise the hotel was nice. "
Helen 3-night trip
Posted 14 hours ago
Grand Hyatt Tampa Bay