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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Oldsmar cottages

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

Cottage in Port Tampa City

Family-friendly Tampa Home < 3 Mi to Ocean!
3.0 star property
10.0 out of 10, Exceptional, (4)
"Located in a quiet, Safe area. The Duplex was clean and had adequate amenities."
United States
David
The price is AED 496
AED 1,352 total
includes taxes & fees
11 Dec - 12 Dec
Family-friendly Tampa Home < 3 Mi to Ocean!
Exterior
The White Door Studio.

Cottage in Lutz

The White Door Studio.
2.0 star property
The price is AED 327
AED 440 total
includes taxes & fees
6 Jan - 7 January 2026
The White Door Studio.
Property grounds
Adorable Waterfront Cottage

Cottage in Odessa

Adorable Waterfront Cottage
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.
The price is AED 459
AED 1,045 total
includes taxes & fees
11 Dec - 12 Dec
Adorable Waterfront Cottage
Exterior
Peaceful cottage with AC in St. Petersburg - Close to Everything!

Cottage in St. Petersburg

Peaceful cottage with AC in St. Petersburg - Close to Everything!
10.0 out of 10, Exceptional, (1)
"Excellent host - Very customer service oriented."
United States
Linda C.
The price is AED 364
AED 907 total
includes taxes & fees
11 Dec - 12 Dec
Peaceful cottage with AC in St. Petersburg - Close to Everything!
Property grounds
Key West Style Cottage - with pool/hot-tub

Cottage in Dunedin

Key West Style Cottage - with pool/hot-tub
10.0 out of 10, Exceptional, (10)
"The property was amazing, beautiful and well thought out! We will be back for sure."
United States
James T.
The price is AED 500
AED 928 total
includes taxes & fees
10 Jan - 11 January 2026
Key West Style Cottage - with pool/hot-tub
Terrace/patio
Cozy Cottage - Close to Everything, Nature Lovers Dream!

Cottage in Odessa

Cozy Cottage - Close to Everything, Nature Lovers Dream!
10.0 out of 10, Exceptional, (65)
"The property was clean and located near where we needed to be. The horses were adorable. Will definitely stay again. "
United States
Janet T.
The price is AED 526
AED 1,361 total
includes taxes & fees
15 Dec - 16 Dec
Cozy Cottage - Close to Everything, Nature Lovers Dream!
Exterior
St Pete/gulfport Tiny little small home

Cottage in St. Petersburg

St Pete/gulfport Tiny little small home
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.
The price is AED 584
AED 1,500 total
includes taxes & fees
9 Jan - 10 January 2026
St Pete/gulfport Tiny little small home
Terrace/patio
Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub

Cottage in Palm Harbor

Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub
10.0 out of 10, Exceptional, (17)
"Home was exactly as advertised. Will stay here again when in the area."
United Kingdom
Michelle H.
The price is AED 494
AED 1,144 total
includes taxes & fees
13 Dec - 14 Dec
Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub
Outdoor dining
Amazing cottage in sunny Tampa close to everything.

Cottage in Lowry Park Central

Amazing cottage in sunny Tampa close to everything.
2.0 star property
The price is AED 441
AED 1,027 total
includes taxes & fees
11 Dec - 12 Dec
Amazing cottage in sunny Tampa close to everything.
Terrace/patio
Sea-clusion: Private Poolside Cottage by the Beach

Cottage in Clearwater

Sea-clusion: Private Poolside Cottage by the Beach
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.
The price is AED 283
AED 823 total
includes taxes & fees
17 Dec - 18 Dec
Sea-clusion: Private Poolside Cottage by the Beach
House (1 Bedroom) | Interior
Cozy St Pete Home ~ 2 Mi to Madeira Beach!

Cottage in Bay Pines

Cozy St Pete Home ~ 2 Mi to Madeira Beach!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Spacious for a one bedroom flat. Exceptionally quiet. Would stay there again. A good value. "
United States
HELEN
The price is AED 294
AED 893 total
includes taxes & fees
11 Dec - 12 Dec
Cozy St Pete Home ~ 2 Mi to Madeira Beach!
Outdoor dining
The Seaside Cottages are located just across the street from Indian Rocks Beach!

Cottage in Indian Rocks Beach

The Seaside Cottages are located just across the street from 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.
The price is AED 433
AED 1,133 total
includes taxes & fees
11 Dec - 12 Dec
The Seaside Cottages are located just across the street from Indian Rocks Beach!
Exterior
Charming 1-bedroom Cottage - Close to Downtown/Sponge Docks/Beaches/Trails

Cottage in Tarpon Springs

Charming 1-bedroom Cottage - Close to Downtown/Sponge Docks/Beaches/Trails
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.
The price is AED 459
AED 1,040 total
includes taxes & fees
16 Dec - 17 Dec
Charming 1-bedroom Cottage - Close to Downtown/Sponge Docks/Beaches/Trails
Property grounds
The Cook Cottage sleeps 4 in Dunedin

Cottage in Downtown Dunedin

The Cook Cottage sleeps 4 in Dunedin
10.0 out of 10, Exceptional, (32)
"Really great hidden gem!"
United States
Greggory
The price is AED 422
AED 1,481 total
includes taxes & fees
11 Dec - 12 Dec
The Cook Cottage sleeps 4 in Dunedin
Terrace/patio
Sleeps 6 Daily Rentals, Pets OK, Hot Tub

Cottage in Clearwater

Sleeps 6 Daily Rentals, Pets OK, Hot Tub
8.6 out of 10, Excellent, (55)
"Great stay. Place was clean and me, my family and my pets enjoyed the stay. Host was really communicative and nice. Definitely coming back."
United States
Alejandro C.
The price is AED 526
AED 1,356 total
includes taxes & fees
11 Dec - 12 Dec
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
Exterior
Openings for October and November at our Beach Cottage-3 minutes to the Gulf!

Cottage in Largo

Openings for October and November at our Beach Cottage-3 minutes to the Gulf!
9.6 out of 10, Exceptional, (5)
"The property was beautiful and beachy! So many small special touches! Wish we had more time, and could have stayed longer! I will definitely be back on my next trip down!"
United States
Brandy
The price is AED 533
AED 1,431 total
includes taxes & fees
5 Jan - 6 January 2026
Openings for October and November at our Beach Cottage-3 minutes to the Gulf!
Exterior
Blushing Flamingo- Triplex with heated pool, across the street from the beach

Cottage in Indian Rocks Beach

Blushing Flamingo- Triplex with heated pool, across the street from the 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.
The price is AED 657
AED 1,508 total
includes taxes & fees
22 Dec - 23 Dec
Blushing Flamingo- Triplex with heated pool, across the street from the beach
Property grounds
Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes

Cottage in Historic Old Northeast

Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
10.0 out of 10, Exceptional, (4)
"The location is great. in a few minutes you are in North Shore Park walking along Tampa Bay. The cottage was clean and cozy. We just might rent it again next time we visit family in the area."
United States
Cynthia S.
Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
Exterior
100 Steps to the Beach, Family and Pet friendly Real Beach Cottage

Cottage in Clearwater

100 Steps to the Beach, Family and Pet friendly Real Beach Cottage
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.
The price is AED 459
AED 1,933 total
includes taxes & fees
13 Dec - 14 Dec
100 Steps to the Beach, Family and Pet friendly Real Beach Cottage
Outdoor dining
The Purple Flower - 30 Second walk to the Beach. Free parking.

Cottage in Clearwater

The Purple Flower - 30 Second walk to the Beach. Free parking.
9.8 out of 10, Exceptional, (203)
"Fabulous location, and the accommodation had everything we needed as a family of 4 to enjoy Clearwater Beach."
United Kingdom
Martin H.
The price is AED 360
AED 837 total
includes taxes & fees
18 Dec - 19 Dec
The Purple Flower - 30 Second walk to the Beach. Free parking.
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

OASIS BAY SUITES, Tampa, Busch Gardens, USF

OASIS BAY SUITES, Tampa, Busch Gardens, USF

10/10 Excellent
"The room was clean, and the staff were extraordinarily kind at the front desk. What a wonderful experience all around. "
Kimberly 1-night trip
Posted 2 days ago
OASIS BAY SUITES, Tampa, Busch Gardens, USF

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