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Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

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 $252
CA $469 total
includes taxes & fees
Aug 11 - Aug 12
The Purple Flower - 30 Second walk to the Beach. Free parking.
Charming Beach Cottage just steps away from Beautiful Clearwater Beach!!
Exterior

Charming Beach Cottage just steps away from Beautiful Clearwater Beach!!

10.0 out of 10, Exceptional, (10)
"A newly remodeled and great place! "
Charming Beach Cottage just steps away from Beautiful Clearwater Beach!!
Key West Style Cottage - with pool/hot-tub
Property grounds

Key West Style Cottage - with pool/hot-tub

8.8 out of 10, Excellent, (15)
"Close to downtown very lovely looking location "
The price is CA $90
CA $238 total
includes taxes & fees
Aug 10 - Aug 11
Key West Style Cottage - with pool/hot-tub
Downtown Dunedin Cottage Near Beaches + Breweries
Exterior

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
Perfect Cottage In Art District of Gulfport
Exterior

Perfect Cottage In Art District of Gulfport

9.6 out of 10, Exceptional, (94)
"This place was absolutely amazing. Such a perfect location. Quiet, serene, clean, and lovely. If I can, I will definitely stay here again. Hosts were responsive to questions. And cottage binder had great suggestions for restaurants. "
Perfect Cottage In Art District of Gulfport
Frenchy's Cottage 490 in Clearwater Beach
Exterior

Frenchy's Cottage 490 in Clearwater Beach

9.8 out of 10, Exceptional, (32)
"Very good property and quick to respond "
Frenchy's Cottage 490 in Clearwater Beach
Adorable Waterfront Cottage
Terrace/patio

Adorable Waterfront Cottage

9.8 out of 10, Exceptional, (17)
"Michael’s place was great and he was super accommodating! "
Adorable Waterfront Cottage
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
Property grounds

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

9.6 out of 10, Exceptional, (109)
"Place was well furnished and looked just like pictures online. Small issue with sink but handled quickly the next morning. Location perfect with short walk to beautiful beach. "
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
The Flip Flop Waterfront Beach Retreat - Close to Beaches
Terrace/patio

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 $131
CA $301 total
includes taxes & fees
Aug 10 - Aug 11
The Flip Flop Waterfront Beach Retreat - Close to Beaches
Welcome to the Jungle- Triplex across the street from the beach, heated pool
Property grounds

Welcome to the Jungle- Triplex across the street from the beach, heated pool

Welcome to the Jungle- Triplex across the street from the beach, heated pool
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, (8)
"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!
Historic Tarpon Springs Abode ~ 3 Mi to Beach
Exterior

Historic Tarpon Springs Abode ~ 3 Mi to Beach

10.0 out of 10, Exceptional, (41)
"Beautiful place, plenty of space and easy access to everything!"
Historic Tarpon Springs Abode ~ 3 Mi to Beach
Grove Keeper Cottage unit has a tree house atmosphere
Property grounds

Grove Keeper Cottage unit has a tree house atmosphere

10.0 out of 10, Exceptional, (37)
"Nicely landscaped grounds, walkable to downtown and beaches. Will stay again..."
Grove Keeper Cottage unit has a tree house atmosphere
Private Surf Shack Less Than 5 Minutes to Indian Rocks Beach Bikes Included!
Property grounds

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

10.0 out of 10, Exceptional, (21)
"Beautiful option for the beach."
Private Surf Shack Less Than 5 Minutes to Indian Rocks Beach Bikes Included!
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!
100 Steps to Beach. Pets Ok, Real Beach House, Daily Rentals
Exterior

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 $256
CA $844 total
includes taxes & fees
Aug 11 - Aug 12
100 Steps to Beach. Pets Ok, Real Beach House, Daily Rentals
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, (140)
"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!
Private family waterfront beach cottage. Best location step out to bay and gulf
Exterior

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

9.0 out of 10, Wonderful, (91)
"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
Cozy and roomy cottage
Outdoor pool

Cozy and roomy cottage

10.0 out of 10, Exceptional, (56)
"We absolutely loved our stay here!The pool area was a tropical paradise (just wish the pool had been heated)! It was so relaxing and peaceful. Our unit was beautifully decorated and very comfortable.The location was perfect for us - Dunedin is a quaint little town, close to Clearwater, but off the beaten path."
Cozy and roomy cottage
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
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

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

10/10 Excellent
"There was only one elevator working throughout our entire stay, therefore very long lines getting to our room at night. Otherwise, everything was great "
Emily 3-night trip
Posted 18 hours ago
Wyndham Grand Clearwater Beach