Search Oldsmar Cottages

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Aug 15 - Aug 17
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Cottages in Oldsmar

The Purple Flower - 30 Second walk to the Beach. Free parking.
Enjoy al fresco dining on the patio with a table and chairs surrounded by a fence, grill, and lush greenery.

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! "
$296 nightly
The price is $330
Aug 18 - Aug 19
Total includes taxes and fees
The Purple Flower - 30 Second walk to the Beach. Free parking.
Charming Beach Cottage just steps away from Beautiful Clearwater Beach!!
473 Residential Building with a charming porch and a palm tree in a quiet neighborhood.

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
Stunning two-story building with a central entrance and beautifully manicured grounds.

Key West Style Cottage - with pool/hot-tub

8.8 out of 10, Excellent, (15)
"We really enjoyed our stay and the cottage was very clean and quiet! It is within walking distance of shops and restaurants! We would definitely like to stay here again! The pool area and common area were very nice as well!"
$155 nightly
The price is $173
Aug 10 - Aug 11
Total includes taxes and fees
Key West Style Cottage - with pool/hot-tub
Downtown Dunedin Cottage Near Beaches + Breweries
Situated in a quiet neighborhood, this two-story home offers a covered outdoor seating area with a bench and table.

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
Step into the vibrant Gulfport Casino, where the entrance beckons with a bold sign.

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
Stunning ocean views and modern architecture define this coastal hotel's sleek design.

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
Yachtsman*OCEAN FRONT COTTAGE*Right on the sand*sleeps up to 6*Heated Pool
Relax in a beachfront setting with a gabled roof and a circular window, surrounded by palm trees and a white picket fence.

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
Adorable Waterfront Cottage
Step into a charming entrance, where a paved pathway leads to a cozy bench and a welcoming porch with a wreath.

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
Relax in a serene outdoor space with a table and chair, overlooking a tranquil water view.

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. "
$191 nightly
The price is $213
Aug 10 - Aug 11
Total includes taxes and fees
The Flip Flop Waterfront Beach Retreat - Close to Beaches
Welcome to the Jungle- Triplex across the street from the beach, heated pool
Guests may enjoy a backyard with a shed, wooden fence, and artificial turf, perfect for relaxation and recreation.

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

$292 nightly
The price is $326
Aug 12 - Aug 13
Total includes taxes and fees
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!
Enjoy dining under a thatched roof with friends and family in this tropical setting.

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
Surrounded by mature trees, this charming house features a wrap-around porch and a front yard.

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
Enjoy a serene living environment surrounded by lush tropical plants and a well-maintained lawn.

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!
Stroll along the paved walkway, lined with lush greenery and palm trees, to the serene beach.

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!
Stroll along the beachfront pathway to a charming collection of houses, each with its own unique style and character.

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
Guests can enjoy a patio area with seating and a table.

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"
$551 nightly
The price is $614
Aug 11 - Aug 12
Total includes taxes and fees
100 Steps to Beach. Pets Ok, Real Beach House, Daily Rentals
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
Enjoy cooking in this well-lit kitchen with a stainless steel refrigerator, microwave, and toaster.

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

9.8 out of 10, Exceptional, (141)
"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!
Beach Lodge:2 Story Sleeps up to 12* Beach front pavilion* heated pool
Relax on the front porch with two Adirondack chairs and a small table.

Beach Lodge:2 Story Sleeps up to 12* Beach front pavilion* heated pool

9.2 out of 10, Wonderful, (23)
"Beautiful place and great location! Highly recommend staying at this rental property!"
Beach Lodge:2 Story Sleeps up to 12* Beach front pavilion* heated pool
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, (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
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

Hotel South Tampa & Suites

Hotel South Tampa & Suites

10/10 Excellent
"Perfect for our quick trip. The rooms were clean, beds comfortable, and staff was friendly."
Courtney 1-night trip
Posted 8 hours ago
Hotel South Tampa & Suites