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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Compare 41 B&B in Oldsmar with updated reviews, rates, and availability.

Tampa Heights Bungalow
Beach

Tampa Heights Bungalow

3.0 star property
9.6 out of 10, Exceptional, (121)
"Thank you for the great stay!"
$88 nightly
The price is $100
Jun 25 - Jun 26
Total includes taxes and fees
Tampa Heights Bungalow
VIinoy House
Exterior

VIinoy House

3.5 star property
10.0 out of 10, Exceptional, (1)
"Great property. Close to everything in downtown St. Pete"
VIinoy House
The Kenwood Gables Boutique Bed & Breakfast
Lobby sitting area

The Kenwood Gables Boutique Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (36)
"What a great property run by a great team providing excellent service. I cannot wait to go back."
$164 nightly
The price is $185
Jun 30 - Jul 1
Total includes taxes and fees
The Kenwood Gables Boutique Bed & Breakfast
Tropical Breeze Suite – Save 20% This Season
Beach

Tropical Breeze Suite – Save 20% This Season

Tropical Breeze Suite – Save 20% This Season
Private bedroom and private bath at separate end of home with water views.
Exterior

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.
St. Pete Cozy Nook – Up to 20% Off Now
Beach

St. Pete Cozy Nook – Up to 20% Off Now

2.0 star property
6.0 out of 10, (1)
"Easy checkinBathroom was old and could use an update Outdoor area was very dirty and neglected - not as appeared in photos Parking is a pain. Location was great "
St. Pete Cozy Nook – Up to 20% Off Now
Bayside Bliss Escape – Book Early, Save 20%
Beach

Bayside Bliss Escape – Book Early, Save 20%

2.0 star property
10.0 out of 10, Exceptional, (1)
"Very cute, compfy, clean and close to everything that we needed..Bed was very comfy..Enjoyed our stay"
Bayside Bliss Escape – Book Early, Save 20%
Family Retreats 5 minutes to the beach
Private kitchen

Family Retreats 5 minutes to the beach

2.0 star property
$430 nightly
The price is $487
Jul 1 - Jul 2
Total includes taxes and fees
Family Retreats 5 minutes to the beach
The Harbor View Loft – Limited 20% Off Deal
Beach

The Harbor View Loft – Limited 20% Off Deal

2.0 star property
4.8 out of 10, (3)
"We arrived late after our flight was delayed only to find that the door code provided would not work to gain us entry. After hours on the phone with VRBO we gave up. This was around 3am at this point after traveling all day. We couldnt get anyone from the property management company on the phone until the following day at which time they acknowledged that their keypad software was malfunctioning and they offered us less than we paid for the night back as a refund. Whatever you do, stay clear of...
The Harbor View Loft – Limited 20% Off Deal
Urban Comfort Retreat – Save Big, 20% Off
Beach

Urban Comfort Retreat – Save Big, 20% Off

2.0 star property
7.2 out of 10, Good, (5)
"My partner and I stayed here for four nights. We enjoyed the location's closeness to downtown/Central Avenue and ability to walk there.The property itself is okay. It's a bit of a cobbled together building. Parking in the adjacent lot is super convenient but the cigarette butts all over the ground were disgusting.The inside itself is thoughtfully styled and was cleaned well when we arrived. The bed was decently comfortable; I think was memory foam. Tiny seating area is okay, though don't bump...
Urban Comfort Retreat – Save Big, 20% Off
Bayshore Room at ONE Inn, near Downtown St. Pete: Ideal for all guests
Interior

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
Rainy Season Relaxation – Book & Save 20%
Beach

Rainy Season Relaxation – Book & Save 20%

2.0 out of 10, (1)
"This is a 2nd floor unit with no ramp and no elevator. (that was NOT disclosed in the listing) The stairway is steep and has an uneven, unmarked lip at the bottom. I broke my foot on that uneven lip within 12 hours of arriving. I have not heard ONE word from the owner about this. The unit is not as advertised... it is not a fully functioning kitchen. The kitchen had no running water. It took 5 days for the owner to respond and tell me there is a sensor somewhere to make the water run. I...
Rainy Season Relaxation – Book & Save 20%
St. Pete Urban Oasis – Hot 20% Savings Inside
Beach

St. Pete Urban Oasis – Hot 20% Savings Inside

6.6 out of 10, (4)
"Perfect for the stay that I was looking for. "
St. Pete Urban Oasis – Hot 20% Savings Inside
Master BR private full bath,private entrance, exlusive use of pool, safe, quiet!
Outdoor pool

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

9.6 out of 10, Exceptional, (63)
"We stayed for a couple nights. All the little extras like snacks and drinks were appreciated! Totally private -we didnt really see or hear the hosts. Definitely will stay again when in the area. Thanks again!"
$144 nightly
The price is $161
Jun 25 - Jun 26
Total includes taxes and fees
Master BR private full bath,private entrance, exlusive use of pool, safe, quiet!
St. Pete Chill Spot – Hot 20% Discount Today
Beach

St. Pete Chill Spot – Hot 20% Discount Today

2.0 star property
10.0 out of 10, Exceptional, (1)
"I really enjoyed my stay. Check in process was smooth and easy. The place was very clean. The bed was very comfortable and the shower was so luxurious after a long day. "
St. Pete Chill Spot – Hot 20% Discount Today
Bright Bayside Loft – Limited 20% Off Deal
Beach

Bright Bayside Loft – Limited 20% Off Deal

2.0 star property
8.0 out of 10, Very Good, (1)
Bright Bayside Loft – Limited 20% Off Deal
Oak Room at ONE Inn, steps to Downtown St. Pete: Ideal for all guests!
Interior

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

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!
Modern One-Bed High-Rise Oasis in Downtown Tampa
Pool

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."
$266 nightly
The price is $298
Jun 29 - Jun 30
Total includes taxes and fees
Modern One-Bed High-Rise Oasis in Downtown Tampa
St. Pete Sunshine Loft – Big Savings, 20% Off
Beach

St. Pete Sunshine Loft – Big Savings, 20% Off

2.0 star property
7.0 out of 10, Good, (2)
"Cute place! It doesn't look like much from the outside, but the room itself was cute, very clean, and had a really comfortable bed. There was a slight snafu with the door code, and when I called they immediately picked up and took care of it. Great service. Walkable to a lot of great restaurants, parks, and museums."
St. Pete Sunshine Loft – Big Savings, 20% Off
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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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.