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Dec 12 - Dec 14
In two months
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In three months
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In four months
Mar 20 - Mar 22

Cottages in Oldsmar

House (2 Bedrooms) | Interior
Family-friendly Tampa Home < 3 Mi to Ocean!

Family-friendly Tampa Home < 3 Mi to Ocean!

3.0 star property
Port Tampa City
10.0 out of 10, Exceptional, (3)
"Located in a quiet, Safe area. The Duplex was clean and had adequate amenities."
United States
David
$342 nightly
The price is $384
Nov 29 - Nov 30
Total with taxes and fees
Family-friendly Tampa Home < 3 Mi to Ocean!
Property grounds
Adorable Waterfront Cottage

Adorable Waterfront Cottage

Odessa
9.6 out of 10, Exceptional, (20)
"Very cute little cottage. If going to the area again, will definitely stay again. "
United States
Pauline O.
$256 nightly
The price is $287
Nov 29 - Nov 30
Total with taxes and fees
Adorable Waterfront Cottage
Exterior
The White Door Studio.

The White Door Studio.

2.0 star property
Lutz
$105 nightly
The price is $115
Dec 1 - Dec 2
Total with taxes and fees
The White Door Studio.
Exterior
Fabulous 2-bedroom cottage with AC in Largo

Fabulous 2-bedroom cottage with AC in Largo

Largo
10.0 out of 10, Exceptional, (3)
"Polly is an amazing host, doing everything possible to accommodate our requests during our stay in this cute little cottage. "
United States
Amy A.
$283 nightly
The price is $316
Nov 28 - Nov 29
Total with taxes and fees
Fabulous 2-bedroom cottage with AC in Largo
Terrace/patio
Cozy Cottage - Close to Everything, Nature Lovers Dream!

Cozy Cottage - Close to Everything, Nature Lovers Dream!

Odessa
10.0 out of 10, Exceptional, (64)
"The property was clean and located near where we needed to be. The horses were adorable. Will definitely stay again. "
United States
Janet T.
$331 nightly
The price is $371
Nov 29 - Nov 30
Total with taxes and fees
Cozy Cottage - Close to Everything, Nature Lovers Dream!
Property grounds
Key West Style Cottage - with pool/hot-tub

Key West Style Cottage - with pool/hot-tub

Dunedin
10.0 out of 10, Exceptional, (4)
"In the heart of Dunedin. Clean and lovely place to stay. Met all our needs. "
United States
sharon h.
$155 nightly
The price is $173
Dec 1 - Dec 2
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
Property grounds
"The Salty Lime" Walk to Restaurant/bars, park.

"The Salty Lime" Walk to Restaurant/bars, park.

Port Richey
10.0 out of 10, Exceptional, (1)
"So well stocked! Thank you, James. We so enjoyed our stay. We two octogenarians loved this place; spotless, super equipped and tasteful. Outside patio was perfect.Nice job, James!"
United States
Theresa B.
$292 nightly
The price is $323
Dec 8 - Dec 9
Total with taxes and fees
"The Salty Lime" Walk to Restaurant/bars, park.
Exterior
Charming 1-bedroom Cottage - Close to Downtown/Sponge Docks/Beaches/Trails

Charming 1-bedroom Cottage - Close to Downtown/Sponge Docks/Beaches/Trails

Tarpon Springs
10.0 out of 10, Exceptional, (3)
"Excellent property close to the Sponge Docks area. The host is very responsive and I will definitely stay here again."
United States
Dee S.
$233 nightly
The price is $259
Dec 1 - Dec 2
Total with taxes and fees
Charming 1-bedroom Cottage - Close to Downtown/Sponge Docks/Beaches/Trails
Terrace/patio
Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub

Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub

Palm Harbor
10.0 out of 10, Exceptional, (16)
"Home was exactly as advertised. Will stay here again when in the area."
United Kingdom
Michelle H.
$263 nightly
The price is $292
Nov 30 - Dec 1
Total with taxes and fees
Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub
Exterior
St Pete/gulfport Tiny little small home

St Pete/gulfport Tiny little small home

St. Petersburg
10.0 out of 10, Exceptional, (3)
"The house was decorated nicely, it was clean, and inside/outside was well kept. The hosts were lovely and responded quickly to questions with precise information. If I need a place to stay in Gulfport again, I would not hesitate to stay!"
United States
Karen J.
$395 nightly
The price is $441
Nov 26 - Nov 27
Total with taxes and fees
St Pete/gulfport Tiny little small home
House (2 Bedrooms) | Interior
Tampa House w/ Patio, Near Downtown & Beaches!

Tampa House w/ Patio, Near Downtown & Beaches!

3.0 star property
Port Tampa City
9.0 out of 10, Wonderful, (2)
"Our quick getaway staying here was amazing. This place is exactly as described and the owner is very responsive. It is a beautiful place, near shopping, food and beaches. I would stay here again! "
United States
Keia
$342 nightly
The price is $384
Nov 29 - Nov 30
Total with taxes and fees
Tampa House w/ Patio, Near Downtown & Beaches!
Exterior
Blushing Flamingo- Triplex with heated pool, across the street from the beach

Blushing Flamingo- Triplex with heated pool, across the street from the beach

Indian Rocks Beach
10.0 out of 10, Exceptional, (1)
"We were happy with rental. Everything was clean. The unit was very well stocked with everything. A lot of beach gear. LocaPlenty of parking "
United States
Wayne F.
$284 nightly
The price is $317
Nov 26 - Nov 27
Total with taxes and fees
Blushing Flamingo- Triplex with heated pool, across the street from the beach
Outdoor dining
The Seaside Cottages are located just across the street from Indian Rocks Beach!

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

Indian Rocks Beach
9.8 out of 10, Exceptional, (11)
"My husband and I enjoyed our time at The Seaside Cottages (#3). The cottage was clean and updated. Short walk to the beach and the pool was nice. We would highly recommend to stay here for a getaway!"
United States
Lacey M.
$283 nightly
The price is $316
Nov 30 - Dec 1
Total with taxes and fees
The Seaside Cottages are located just across the street from Indian Rocks Beach!
Exterior
Peaceful cottage with AC in St. Petersburg - Close to Everything!

Peaceful cottage with AC in St. Petersburg - Close to Everything!

St. Petersburg
10.0 out of 10, Exceptional, (1)
"Excellent host - Very customer service oriented."
United States
Linda C.
$278 nightly
The price is $310
Nov 26 - Nov 27
Total with taxes and fees
Peaceful cottage with AC in St. Petersburg - Close to Everything!
Outdoor dining
The Purple Flower - 30 Second walk to the Beach. Free parking.

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

Clearwater
9.8 out of 10, Exceptional, (199)
"Fabulous location, and the accommodation had everything we needed as a family of 4 to enjoy Clearwater Beach."
United Kingdom
Martin H.
$206 nightly
The price is $230
Nov 26 - Nov 27
Total with taxes and fees
The Purple Flower - 30 Second walk to the Beach. Free parking.
Outdoor dining
Amazing cottage in sunny Tampa close to everything.

Amazing cottage in sunny Tampa close to everything.

2.0 star property
Lowry Park Central
$250 nightly
The price is $280
Nov 26 - Nov 27
Total with taxes and fees
Amazing cottage in sunny Tampa close to everything.
Property grounds
Rave Reviews Walk to Downtown Dunedin & Waterfront Pets Ok -Barefoot Parrot 1

Rave Reviews Walk to Downtown Dunedin & Waterfront Pets Ok -Barefoot Parrot 1

Downtown Dunedin
10.0 out of 10, Exceptional, (15)
"Great location! Clean, dog friendly, great communication and tips from owner!"
United States
Dawn H.
$306 nightly
The price is $342
Dec 3 - Dec 4
Total with taxes and fees
Rave Reviews Walk to Downtown Dunedin & Waterfront Pets Ok -Barefoot Parrot 1
Exterior
100 Steps to the Beach, Family and Pet friendly Real Beach Cottage

100 Steps to the Beach, Family and Pet friendly Real Beach Cottage

Clearwater
9.2 out of 10, Wonderful, (58)
"Very friendly staff. Capt Al was very accommodating. Highly recommend for a family vacation. "
United States
Char D.
$524 nightly
The price is $585
Dec 13 - Dec 14
Total with taxes and fees
100 Steps to the Beach, Family and Pet friendly Real Beach Cottage
Terrace/patio
Sea-clusion: Private Poolside Cottage by the Beach

Sea-clusion: Private Poolside Cottage by the Beach

Clearwater
9.0 out of 10, Wonderful, (4)
"We absolutely loved staying here and cant wait to book it again. It was very clean and nicely decorated. We were close to everything we needed within walking distance! The pool was nice and warm also. Highly recommend staying here."
United States
Amanda S.
$210 nightly
The price is $235
Dec 7 - Dec 8
Total with taxes and fees
Sea-clusion: Private Poolside Cottage by the Beach
Outdoor dining
Stay steps from the sand in this charming single-family home. Enjoy exclusive beach access at Sunburst Inn, featured on HGTV. Cozy comfort for up to 4, and an unbeatable location on the Gulf. Perfect for a romantic escape or small family getaway.

Stay steps from the sand in this charming single-family home. Enjoy exclusive beach access at Sunburst Inn, featured on HGTV. Cozy comfort for up to 4, and an unbeatable location on the Gulf. Perfect for a romantic escape or small family getaway.

Indian Shores
9.8 out of 10, Exceptional, (22)
"Had a great time no complaints"
United States
Jarrod P.
$383 nightly
The price is $419
Nov 28 - Nov 29
Total with taxes and fees
Stay steps from the sand in this charming single-family home. Enjoy exclusive beach access at Sunburst Inn, featured on HGTV. Cozy comfort for up to 4, and an unbeatable location on the Gulf. Perfect for a romantic escape or small family getaway.
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

Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

10/10 Excellent
"Room was extremely clean, loved the very large tv. Check in staff was very accommodating "
Carol 1-night trip
Posted 12 hours ago
Hilton Tampa Airport Westshore

Find out more about Oldsmar

Oldsmar Cottages information

Number of reviews
414
Accommodation
500 Cottages
Lowest Price
$115
Highest Price
$585

Frequently asked questions

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We think that a vacation should be simple, so if you're looking for cottages in Oldsmar at an affordable rate, Expedia has you covered. Stick to the budget and select a cheap option surrounded by wilderness, or book an upscale cottage to spoil your loved ones.
How can I find cheap cottages in Oldsmar?
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What is there to do in Oldsmar near my cottage?
If you're ready to discover the sights of Oldsmar, be sure to visit Oldsmar Flea Market. It's a winner with locals and travelers alike.

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