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Cottages in Oldsmar

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

9.0 out of 10, Wonderful, (94)
"10/10 exactly what was advertised. Beautiful beach. "
Private family waterfront beach cottage. Best location step out to bay and gulf

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

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

9.8 out of 10, Exceptional, (60)
"The house is right across the street from beach access. It was the perfect place to stay for our trip"
“A” Beachy Keen Cottage! Just Steps From Indian Rocks Beach!

THE COTTAGE - 32 Steps to the Beach - Sleeps 2, drive to your door, Wifi, Grill.

9.8 out of 10, Exceptional, (144)
"Very nice cottage. Great location. "
THE COTTAGE - 32 Steps to the Beach - Sleeps 2, drive to your door, Wifi, Grill.

Historic Beach Cottage steps from beach. Pet friendly!

9.2 out of 10, Wonderful, (122)
"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 AED 493
AED 1,311 total
includes taxes & fees
3 Sep - 4 Sep
Historic Beach Cottage steps from beach. Pet friendly!

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

9.8 out of 10, Exceptional, (192)
"Loved this place! Perfect with all the needed amenities. Will definitely stay here again if in the area."
The price is AED 507
AED 1,039 total
includes taxes & fees
3 Sep - 4 Sep
The Purple Flower - 30 Second walk to the Beach. Free parking.

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

9.6 out of 10, Exceptional, (112)
"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!

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!

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 AED 261
AED 704 total
includes taxes & fees
3 Sep - 4 Sep
The Flip Flop Waterfront Beach Retreat - Close to Beaches

Canary Beach Cottage - steps to the sand!

9.6 out of 10, Exceptional, (47)
"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!

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

9.8 out of 10, Exceptional, (145)
"We loved the stay there. It is very close to the beach. One of the best places I’ve stayed at in a long time. "
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!!

9.8 out of 10, Exceptional, (217)
"My wife & I totally enjoyed our stay in Linda’s little bungalow on the ocean. Perfect beach location."
BEACHFRONT COTTAGE! Step out the door and into the sand! On the Gulf of Mexico!!

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

9.8 out of 10, Exceptional, (55)
"Perfect beach house for a single family! The kids loved the convenience of being on the beach and the heated pool. "
Yachtsman*OCEAN FRONT COTTAGE*Right on the sand*sleeps up to 6*Heated Pool

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

10.0 out of 10, Exceptional, (160)
"We had the greatest time thanks to Myrtle! Perfect little getaway in the best location and so close to the airport!"
Beachfront Cottages (Patio) at Beautiful Sandy Shores on Gulf of Mexico

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

10.0 out of 10, Exceptional, (78)
"It was a great little slice of heaven on the river. Loved the experience."
Riverside Casita: semi-private pool, spa, dock, garden oasis, 5 min to downtown!

Grove Keeper Cottage unit has a tree house atmosphere

10.0 out of 10, Exceptional, (38)
"Really enjoyed the privacy that this spot gave us from the area. The landscaping was beautiful. There are a lot of great places to eat right around the corner. "
Grove Keeper Cottage unit has a tree house atmosphere

Kayaks, Canoe, Private Lake Community

9.2 out of 10, Wonderful, (15)
"Great place and hosts! "
The price is AED 393
AED 834 total
includes taxes & fees
3 Sep - 4 Sep
Kayaks, Canoe, Private Lake Community

Charming Upstairs Unit in a Cottage, steps to the beach. Across from John's Pass

9.4 out of 10, Exceptional, (148)
"Comfortable, no-frills stay for one or a couple. Easy access to beach as well as restaurants and shopping at John’s Pass. Handy parking, nice deck and patio with grill. A few basic items that would be helpful: kitchen linens, basic storage containers and hand soap. "
Charming Upstairs Unit in a Cottage, steps to the beach. Across from John's Pass

Beautiful luxury 2 bedroom private Cottage

10.0 out of 10, Exceptional, (23)
"Had an absolutely glorious stay. Property is gorgeous and tranquil. Thank you for creating this haven and sharing it 3"
Beautiful luxury 2 bedroom private Cottage

Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes

10.0 out of 10, Exceptional, (3)
"The property was so well appointed with a cute decor. Everything was clean and well stocked with necessities. Enjoyed our visit, highly recommend!"
The price is AED 754
AED 1,572 total
includes taxes & fees
3 Sep - 4 Sep
Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
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

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