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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

Tampa Heights Bungalow - Bed & Breakfast
Kayaking

Tampa Heights Bungalow - Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (102)
"We have never stayed at a bed and breakfast place before, ww was very pleased with the place we would definitely rebook. Bed is super comfy. "
The price is AED 207
AED 295 total
includes taxes & fees
18 May - 19 May
Tampa Heights Bungalow - Bed & Breakfast
Private bedroom and private bath at separate end of home with water views.

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

9.6 out of 10, Exceptional, (36)
"Anna is a wonderful host. Very comfortable stay! "
Private bedroom and private bath at separate end of home with water views.
Downtown Hideaway - Spring Savings
Beach

Downtown Hideaway - Spring Savings

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...
Downtown Hideaway - Spring Savings
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, (60)
"Quiet and safe stay!"
The price is AED 327
AED 586 total
includes taxes & fees
27 May - 28 May
Master BR private full bath,private entrance, exlusive use of pool, safe, quiet!
Bloom & Relax Retreat – Save Big 20% off!
Beach

Bloom & Relax Retreat – Save Big 20% off!

2.0 star property
Bloom & Relax Retreat – Save Big 20% off!
Sunset Serenade - 20% Spring Discount
Beach

Sunset Serenade - 20% Spring Discount

2.0 star property
6.6 out of 10, (4)
"Unit was clean and perfect size for 2 people. Loved that we were able to take our fur babies with us. Walls are a little thin so you can hear people upstairs above unit but not too bad. Great location access to highway and all the downtown spots. Very accommodating and responsive host. "
Sunset Serenade - 20% Spring Discount
St Pete Serenity – Spring Special!
Beach

St Pete Serenity – Spring Special!

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 Serenity – Spring Special!
Serene Oasis Tampa Home /Pool /Hot Tub/Game Room
Outdoor dining

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
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."
The price is AED 602
AED 680 total
includes taxes & fees
1 Jun - 2 Jun
The Kenwood Gables Boutique Bed & Breakfast
Downtown Oasis – Spring Savings!
Beach

Downtown Oasis – Spring Savings!

6.6 out of 10, (4)
"Perfect for the stay that I was looking for. "
Downtown Oasis – Spring Savings!
Sunshine Escape – Limited-Time Discount!
Beach

Sunshine Escape – Limited-Time Discount!

2.0 star property
2.0 out of 10, (1)
"Black mold, bugs (both dead and alive!), leaking AC units, windows that don’t lock. Terrible. Not making this up… I have photos and videos. Just don’t stay here - it’s cheap for a reason! Did I mention visible black mold!?!? Not clean, not healthy, not safe. "
Sunshine Escape – Limited-Time Discount!
Vibrant Vibes Getaway – Up to 20% Off!
Beach

Vibrant Vibes Getaway – Up to 20% Off!

6.0 out of 10, (2)
"My husband and I stayed for a music festival at Vinoy. Location was great, easy to find, and easy check in."
Vibrant Vibes Getaway – Up to 20% Off!
Coastal Bliss Retreat – Discount Awaits!
Beach

Coastal Bliss Retreat – Discount Awaits!

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"
Coastal Bliss Retreat – Discount Awaits!
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
Shower, hair dryer, towels, soap

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
St. Pete Spring Getaway - Up to 20% Off
Beach

St. Pete Spring Getaway - Up to 20% Off

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 Spring Getaway - Up to 20% Off
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, (3)
"Place is really quaint and in a great neighborhood. Two blocks from anything you wanna do in downtown Saint Pete. Great spot for anything you’re doing on a short term basis."
Oak Room at ONE Inn, steps to Downtown St. Pete: Ideal for all guests!
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
Walnut Room at ONE Inn, Comfy, Steps to Downtown St. Pete: Ideal for all guests!
Interior

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!
Family Retreats 5 minutes to the beach
Private kitchen

Family Retreats 5 minutes to the beach

2.0 star property
Family Retreats 5 minutes to the beach
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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Other property types in Oldsmar

Sailport Waterfront Suites
Beach nearby, beach volleyball, fishing

Sailport Waterfront Suites

3.5 star property
8.4 out of 10, Very Good, (4498)
"This is a very nice resort. We really enjoyed our stay."
The price is AED 369
AED 482 total
includes taxes & fees
1 Jun - 2 Jun
Sailport Waterfront Suites
Sunset Vistas Two Bedroom Beachfront Suites
2 outdoor pools, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers

Sunset Vistas Two Bedroom Beachfront Suites

3.5 star property
8.8 out of 10, Excellent, (3199)
"Amazing location views gorgeous!!!!"
The price is AED 632
AED 806 total
includes taxes & fees
19 May - 20 May
Sunset Vistas Two Bedroom Beachfront Suites
Chase Suite Hotel Rocky Point Tampa
Front of property

Chase Suite Hotel Rocky Point Tampa

3.0 star property
7.6 out of 10, Good, (4923)
"Great stay"
The price is AED 470
AED 529 total
includes taxes & fees
4 May - 5 May
Chase Suite Hotel Rocky Point 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.

Frequently asked questions

Searching for B&Bs in Oldsmar?
Whether you’re on a family vacation and want a small, cozy place to stay, or you’re traveling solo and hoping to get some tips from locals, a B&B can be a good choice for many different types of travelers. When you want to venture out to explore Oldsmar, consider browsing the exhibits at Oldsmar Historical Society Museum.
Why choose a B&B versus a traditional hotel?
With attentive service, an atmosphere suited to mingling with other guests, and of course a full breakfast to start the day, B&Bs offer a unique setting.
What are the best B&Bs in Oldsmar?
Below are some well-liked B&Bs in the surrounding area: Tampa Heights Bungalow - Bed & Breakfast: 3 rooms. 13 mi (21 km) from the heart of Oldsmar. Enjoy the massage services and private yard. The Kenwood Gables Boutique Bed & Breakfast: 5 rooms. 17.6 mi (28.3 km) from the downtown core. Enjoy the free full breakfast and in-room pools. Spring in the City - Downtown St. Pete: Situated 17.8 mi (28.7 km) from the heart of Oldsmar. Private bedroom and private bath at separate end of home with water views.: 13.5 mi (21.6 km) from the heart of downtown. Coastal Bliss Retreat – Discount Awaits!: Located 17.9 mi (28.8 km) from the core of Oldsmar.
What's the best time of year to stay at a B&B in Oldsmar?
When you’re dreaming of a getaway to Oldsmar, be sure to take into account the year-round temperatures. The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 64°F. Average annual precipitation for Oldsmar is 45 inches.
What is there to do in Oldsmar?
Travelers enjoy Oldsmar for its beaches and restaurants. When you want to explore some things to do in town, Tampa Bay and Oldsmar Flea Market are some notable sights to visit. You might check out Oldsmar Historical Society Museum if you have time to see more of the area.
How can I get to and around Oldsmar?
Planning your excursions in and around Oldsmar is easier with these transportation options. Fly into Tampa Intl. Airport (TPA), which is located 8.8 mi (14.2 km) away from the city center. Otherwise, you can search for flights to St. Petersburg-Clearwater Intl. Airport (PIE), which is 9 mi (14.4 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.