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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

B&B in Oldsmar

Tampa Heights Bungalow
Guests can enjoy a peaceful evening on the beach with a palm tree nearby.

Tampa Heights Bungalow

3.0 star property
9.4 out of 10, Exceptional, (130)
"Nice quiet clean relaxing "
$88 nightly
The price is $100
Aug 11 - Aug 12
Total includes taxes and fees
Tampa Heights Bungalow
Modern One-Bed High-Rise Oasis in Downtown Tampa
Relax by the rectangular pool surrounded by lounge chairs and take in the city views.

Modern One-Bed High-Rise Oasis in Downtown Tampa

9.8 out of 10, Exceptional, (7)
"Great location close to the Tampa Riverwalk and lots of restaurants. Place was very clean and exactly what we were expecting based on the listing. Pool area was also great. Would highly recommend this place."
Modern One-Bed High-Rise Oasis in Downtown Tampa
Private bedroom and private bath at separate end of home with water views.
Enjoy outdoor seating on the porch with a small table and two chairs.

Private bedroom and private bath at separate end of home with water views.

9.6 out of 10, Exceptional, (36)
" just looking for a place to sleep , we were gone all day ,small but worked for us , thanks"
Private bedroom and private bath at separate end of home with water views.
The Kenwood Gables Boutique Bed & Breakfast
Experience the classic elegance of this stately living room, featuring a high ceiling, ornate chandelier, and cozy fireplace.

The Kenwood Gables Boutique Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (39)
"What a great property run by a great team providing excellent service. I cannot wait to go back."
The Kenwood Gables Boutique Bed & Breakfast
Family Retreats 5 minutes to the beach
Enjoy cooking in this well-equipped kitchen with a central island and modern appliances.

Family Retreats 5 minutes to the beach

2.0 star property
Family Retreats 5 minutes to the beach
Oak Room at ONE Inn, steps to Downtown St. Pete: Ideal for all guests!
Enter a grand space with a polished floor, white columns, and a stunning chandelier.

Oak Room at ONE Inn, steps to Downtown St. Pete: Ideal for all guests!

10.0 out of 10, Exceptional, (4)
"A very loving property in a nice part of town"
Oak Room at ONE Inn, steps to Downtown St. Pete: Ideal for all guests!
Master BR private full bath,private entrance, exlusive use of pool, safe, quiet!
Relax in a casual dining area with a round table and comfortable chairs, overlooking a pool with a slide.

Master BR private full bath,private entrance, exlusive use of pool, safe, quiet!

9.6 out of 10, Exceptional, (64)
"Pictures doesn't do it justice. Very nice owners that responded quickly to any questions, you will be glad you chose Beach More Worry Less"
$124 nightly
The price is $138
Aug 11 - Aug 12
Total includes taxes and fees
Master BR private full bath,private entrance, exlusive use of pool, safe, quiet!
VIinoy House
Relax in a serene outdoor seating area surrounded by lush greenery and a historic landmark.

VIinoy House

3.5 star property
10.0 out of 10, Exceptional, (1)
"Great property. Close to everything in downtown St. Pete"
VIinoy House
Bayshore Room at ONE Inn, near Downtown St. Pete: Ideal for all guests
Enter a grand space with a polished floor, a grand door, and a chandelier.

Bayshore Room at ONE Inn, near Downtown St. Pete: Ideal for all guests

10.0 out of 10, Exceptional, (2)
"Lovely historic property easy walk to all the downtown shops, restaurants, bars, museums and more."
Bayshore Room at ONE Inn, near Downtown St. Pete: Ideal for all guests
Northshore Room at ONE Inn, steps to Downtown St. Pete: Ideal for all guests!
Enter a beautifully designed entryway with a high ceiling, decorative chandelier, and elegant columns.

Northshore Room at ONE Inn, steps to Downtown St. Pete: Ideal for all guests!

9.4 out of 10, Exceptional, (3)
"Just one comment (very personal), I would have liked a harder mattress."
Northshore Room at ONE Inn, steps to Downtown St. Pete: Ideal for all guests!
Poplar Room at ONE Inn, Cozy, steps to Downtown St. Pete: Ideal for all guests
Classic entryway with a chandelier, polished floors, and white columns.

Poplar Room at ONE Inn, Cozy, steps to Downtown St. Pete: Ideal for all guests

9.4 out of 10, Exceptional, (3)
"Clean and located within walking distance to the St Pete Pier."
Poplar Room at ONE Inn, Cozy, steps to Downtown St. Pete: Ideal for all guests
Luxury Bay Room at ONE Inn, steps to Downtown St. Pete: Ideal for all guests
Enter a grand space with a high ceiling, polished floors, and a stunning chandelier.

Luxury Bay Room at ONE Inn, steps to Downtown St. Pete: Ideal for all guests

9.6 out of 10, Exceptional, (5)
"Very peaceful place to stay during the holidays. Location was excellent."
Luxury Bay Room at ONE Inn, steps to Downtown St. Pete: Ideal for all guests
Elm Room Bay at ONE Inn, steps to Downtown St. Pete: Ideal for all guests
Classic entryway with a high ceiling, white columns, and a central chandelier.

Elm Room Bay at ONE Inn, steps to Downtown St. Pete: Ideal for all guests

9.0 out of 10, Wonderful, (2)
"1 sink in our room doesn't drain. And 1 pillow case had a look like blood stain. "
Elm Room Bay at ONE Inn, steps to Downtown St. Pete: Ideal for all guests
Exquisite Home near Tampa/Orlando sleeps 14-20.
Relax in comfort with a cozy sofa, a neatly made bed, and a dining area.

Exquisite Home near Tampa/Orlando sleeps 14-20.

Exquisite Home near Tampa/Orlando sleeps 14-20.
Walnut Room at ONE Inn, Comfy, Steps to Downtown St. Pete: Ideal for all guests!
Enter a beautifully designed entryway with polished floors, tall columns, and a stunning chandelier.

Walnut Room at ONE Inn, Comfy, Steps to Downtown St. Pete: Ideal for all guests!

9.0 out of 10, Wonderful, (2)
"Beautiful, clean and comfortable property. Host was very responsive and helpful. You can bring your favorite coffee or teas and use the fully equipped kitchen. Parking passes were helpful and the neighborhood was very safe and quiet. "
Walnut Room at ONE Inn, Comfy, Steps to Downtown St. Pete: Ideal for all guests!
Serene Oasis Tampa Home /Pool /Hot Tub/Game Room
Stunning home with a garage, lush greenery, and a charming front porch.

Serene Oasis Tampa Home /Pool /Hot Tub/Game Room

8.0 out of 10, Very Good, (2)
"We had an amazing stay! Everything was as advertised. The house was clean and it was in a very nice quiet neighborhood in a great location close to lots of attractions.The house had everything we needed including plenty of towels for a family of 6. We opted to have the pool heated and we are so glad we did. The days were warm but the nights were chilly. We would definitely stay here again! "
Serene Oasis Tampa Home /Pool /Hot Tub/Game Room
Diamond room 2
Enjoy a peaceful outdoor space with a deck, table, and chairs, surrounded by a picket fence and a beautiful tree.

Diamond room 2

$131 nightly
The price is $146
Aug 18 - Aug 19
Total includes taxes and fees
Diamond room 2
Lovely 2 bedroom 1 bath house near the beach
Fully equipped kitchen with microwave, stove, and coffee maker.

Lovely 2 bedroom 1 bath house near the beach

Lovely 2 bedroom 1 bath house near the beach
nice space to relaxing
Enter a charming home with a welcoming entrance featuring a white door, black shutters, and a cozy seating area.

nice space to relaxing

nice space to relaxing
4306 C - Enchanting Home in Tampa
Interior

4306 C - Enchanting Home in Tampa

4306 C - Enchanting Home in Tampa
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

The Westin Tampa Bay

The Westin Tampa Bay

10/10 Excellent
"Our hotel room was very spacious with amazing views. The bed was very comfortable, slept awesome! I love the private beach to relax on and soak up some sun. Everything was clean and updated. Only down side was that the restaurant was being renovated. More limited and crowded trying to eat in the lobby area. "
Michele 1-night trip
Posted 10 hours ago
The Westin Tampa Bay

Frequently asked questions

What is the nightly rate for a B&B in Oldsmar?
Prices for B&Bs in Oldsmar often vary, but you can find a great deal from $100 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Oldsmar B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Oldsmar?
The best time to book a B&B in Oldsmar is during the peak season from February to April, when the weather is pleasantly warm and outdoor activities abound. This timeframe attracts visitors looking to enjoy the beautiful parks and recreational opportunities that the area has to offer, including hiking and biking along scenic trails.

During these months, temperatures typically range from the low 50s to mid-80s Fahrenheit, creating ideal conditions for exploring the lush surroundings. Visitors can take advantage of the comfortable climate for activities such as kayaking on nearby waters or enjoying picnics in the parks, all while soaking in the vibrant local atmosphere.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter experience, allowing you to enjoy the peaceful ambiance of Oldsmar without the crowds. The weather remains pleasant, making it a wonderful time for leisurely strolls and visits to local attractions at a more relaxed pace.
What is the difference between a Oldsmar Bed and Breakfast and a hotel?
Every Oldsmar B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Oldsmar B&Bs.