A beach at sunset with birds flying and a person walking.

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

Our top choices for Oldsmar bed & breakfast

A dining area with a table and chairs, a decorative tree design on the glass partition, and a view of an outdoor swimming pool.

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

Master BR private full bath,private entrance, exlusive use of pool, safe, quiet!
Greater Northdale
9.6 out of 10, Exceptional, (75 reviews)
"Second time we stayed! We enjoyed it thanks"
United States
Jennifer
The price is CA $98
CA $195 total
includes taxes & fees
Sep 27 - Sep 28
Master BR private full bath,private entrance, exlusive use of pool, safe, quiet!
A beach with clear shallow water and a sandy shore.

2. Tampa Heights Bungalow

Tampa Heights Bungalow
3.0 star property
Tampa Heights
9.6 out of 10, Exceptional, (210 reviews)
"Very cozy and comfortable stay. Very close to the highway and other parts of Tampa. Host was very communicative - I recommend this stay!"
United States
Rebekah
The price is CA $71
CA $105 total
includes taxes & fees
Sep 30 - Oct 1
Tampa Heights Bungalow
A swimming pool with a hot tub, surrounded by a brick deck and a building with large windows and a balcony.

3. Poolside Guest Suite in Mansion with Private Entrance & Bathroom. 4 Guest Max

Poolside Guest Suite in Mansion with Private Entrance & Bathroom. 4 Guest Max
Old Seminole Heights
9.8 out of 10, Exceptional, (6 reviews)
"Clean and cozy, close to airport, great communication with host"
United States
Olga B.
The price is CA $227
CA $286 total
includes taxes & fees
Sep 27 - Sep 28
Poolside Guest Suite in Mansion with Private Entrance & Bathroom. 4 Guest Max
A hotel room with a bed, a desk, a television displaying a menu, a wardrobe, and a door.

4. The Knickerbocker by Delphius

The Knickerbocker by Delphius
3.0 star property
Hyde Park
The price is CA $315
CA $358 total
includes taxes & fees
Sep 27 - Sep 28
The Knickerbocker by Delphius
A cozy lounge area with a neon sign, plush seating, and potted plants.

5. The 1888 Hotel (204) Digital Nomad Queen Suite

The 1888 Hotel (204) Digital Nomad Queen Suite
Downtown St. Petersburg
8.0 out of 10, Very good, (2 reviews)
"Loved being able to connect with a friendly and helpful person when I had questions. Location was excellent and it was great to have parking included at the Museum - which made me go see the Museum too. The room was clean, convenient, and well equipped."
United States
Beate B.
The price is CA $178
CA $230 total
includes taxes & fees
Sep 27 - Sep 28
The 1888 Hotel (204) Digital Nomad Queen Suite
A modern outdoor lounge area with sun loungers, a covered seating area, and a canopy bed.

6. Cabanas of Treasure Island #4

Cabanas of Treasure Island #4
Sunshine Beach
10.0 out of 10, Exceptional, (1 review)
"Such a beautiful quaint place to stay while in Treasure Island. Everything was perfect.I will Highly recommended to all my friends and family."
United States
Susan S.
The price is CA $123
CA $240 total
includes taxes & fees
Sep 30 - Oct 1
Cabanas of Treasure Island #4
A cozy lounge area with a neon sign, plush seating, and potted plants.

7. The 1888 Hotel 302 (A/B/C) 2 Bed/1 Bath King Suite

The 1888 Hotel 302 (A/B/C) 2 Bed/1 Bath King Suite
Downtown St. Petersburg
10.0 out of 10, Exceptional, (2 reviews)
"Very well thought out rooms. Very clean. Had conversation with the GM several times as he was going around personally attending to things. And he found my keys I misplaced. Had a great time there"
United States
Hillary B.
The price is CA $236
CA $296 total
includes taxes & fees
Sep 27 - Sep 28
The 1888 Hotel 302 (A/B/C) 2 Bed/1 Bath King Suite
A covered outdoor seating area with wicker furniture, a central table with a lit candle, and lush greenery in the background.

8. VIinoy House

VIinoy House
3.5 star property
Historic Old Northeast
7.2 out of 10, Good, (5 reviews)
"Beautiful decor and excellent location."
United States
Monica
The price is CA $253
CA $405 total
includes taxes & fees
Oct 27 - Oct 28
VIinoy House
A cozy lounge area with a neon sign, plush seating, and potted plants.

9. The 1888 Hotel (Casita) 2Bed/1Bath Detached

The 1888 Hotel (Casita) 2Bed/1Bath Detached
Downtown St. Petersburg
8.0 out of 10, Very good, (1 review)
"The 1888 is an unconventional “hotel,” really an unmanned guest house but one supported by 24 hour service by phone and text as needed. The reps were extremely responsive to any query and they keep in touch with multiple texts throughout the stay. The Casita is a private cottage at the rear of the property with two bedrooms to sleep 4 and a couch that doubles as a single bed; this place would not sleep 3 couples but it worked out fine for our group of 5. It is nicely appointed with a kitchen...
United States
Rob S.
The price is CA $253
CA $320 total
includes taxes & fees
Sep 30 - Oct 1
The 1888 Hotel (Casita) 2Bed/1Bath Detached
A cozy lounge area with a neon sign, plush seating, and potted plants.

10. The 1888 Hotel (206) Queen Studio Suite

The 1888 Hotel (206) Queen Studio Suite
Downtown St. Petersburg
The price is CA $178
CA $230 total
includes taxes & fees
Sep 27 - Sep 28
The 1888 Hotel (206) Queen Studio Suite
A modern outdoor lounge area with sun loungers, a covered seating area, and a canopy bed.

11. Las Olas of Treasure Island #8

Las Olas of Treasure Island #8
Sunshine Beach
10.0 out of 10, Exceptional, (2 reviews)
"This is my second time staying at this property. Unfortunately, this entire area was hit very hard by the two hurricanes couple of years ago. They have completely renovated the entire place and changed the color scheme and it is just as fantastic, if not better than it was the first time I stayed here!!! The room again was clean and everything was in place.The outside courtyard area had the same kind of furnishings from when i stayed here in 2024.I can tell you that this place is very, very...
United States
Emmitt F.
The price is CA $123
CA $240 total
includes taxes & fees
Sep 30 - Oct 1
Las Olas of Treasure Island #8
A modern outdoor lounge area with sun loungers, a covered seating area, and a canopy bed.

12. Las Olas of Treasure Island #7

Las Olas of Treasure Island #7
Sunshine Beach
10.0 out of 10, Exceptional, (1 review)
"As with the laat 2 visuts, the stay were again spectacular!Veey clean room, quiet, except for the thunderstorm and rain, but ill be using this property again!As stated with a couple of my other reviews, the location couldn't be better. Near everything! Food, entertainment, shopping, sunset views, the beach."
United States
Emmitt F.
The price is CA $123
CA $240 total
includes taxes & fees
Sep 30 - Oct 1
Las Olas of Treasure Island #7
A cozy lounge area with a neon sign, plush seating, and potted plants.

13. The 1888 Hotel (102) ADA

The 1888 Hotel (102) ADA
Downtown St. Petersburg
The price is CA $178
CA $230 total
includes taxes & fees
Sep 27 - Sep 28
The 1888 Hotel (102) ADA
A modern outdoor patio with lounge chairs and a covered seating area, surrounded by palm trees and a building with a white exterior.

14. Las Olas of Treasure Island #9

Las Olas of Treasure Island #9
Sunshine Beach
10.0 out of 10, Exceptional, (2 reviews)
"Worked great for us!"
United States
Amy M.
The price is CA $131
CA $281 total
includes taxes & fees
Sep 28 - Sep 29
Las Olas of Treasure Island #9
A cozy lounge area with a neon sign, plush seating, and potted plants.

15. The 1888 Hotel (205) Honeymoon King Studio

The 1888 Hotel (205) Honeymoon King Studio
Downtown St. Petersburg
The price is CA $212
CA $268 total
includes taxes & fees
Oct 4 - Oct 5
The 1888 Hotel (205) Honeymoon King Studio
A modern outdoor lounge area with sun loungers, a covered seating area, and a canopy bed.

16. Las Olas of Treasure Island #3

Las Olas of Treasure Island #3
Sunshine Beach
7.6 out of 10, Good, (4 reviews)
"Bath a little small but ok"
United States
Wade C.
The price is CA $123
CA $240 total
includes taxes & fees
Sep 28 - Sep 29
Las Olas of Treasure Island #3
A cozy lounge area with a neon sign, plush seating, and potted plants.

17. The 1888 Hotel (305) Honeymoon King Studio

The 1888 Hotel (305) Honeymoon King Studio
Downtown St. Petersburg
The price is CA $193
CA $247 total
includes taxes & fees
Sep 27 - Sep 28
The 1888 Hotel (305) Honeymoon King Studio
A cozy lounge area with a neon sign, plush seating, and potted plants.

18. The 1888 Hotel (306) Queen Studio Suite

The 1888 Hotel (306) Queen Studio Suite
Downtown St. Petersburg
10.0 out of 10, Exceptional, (1 review)
"Cool room and a great location. Pier and beach a short walk away."
United States
Kevin O.
The price is CA $178
CA $230 total
includes taxes & fees
Sep 27 - Sep 28
The 1888 Hotel (306) Queen Studio Suite
A cozy lounge area with a neon sign, plush seating, and potted plants.

19. The 1888 Hotel (103) Queen Studio Suite

The 1888 Hotel (103) Queen Studio Suite
Downtown St. Petersburg
10.0 out of 10, Exceptional, (2 reviews)
"What an awesome stay!! Loved the place and its cleanliness and convenience! Thank you and looking forward to booking again for next year’s event!!"
United States
Jersey O.
The price is CA $199
CA $253 total
includes taxes & fees
Oct 4 - Oct 5
The 1888 Hotel (103) Queen Studio Suite
A cozy lounge area with a neon sign, plush seating, and potted plants.

20. The 1888 Hotel 201(A/B) Lux King 1Bed/Bath

The 1888 Hotel 201(A/B) Lux King 1Bed/Bath
Downtown St. Petersburg
The price is CA $219
CA $276 total
includes taxes & fees
Sep 27 - Sep 28
The 1888 Hotel 201(A/B) Lux King 1Bed/Bath
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

Barefoot Beach Club

Barefoot Beach Club

8/10 Good
"Property was well kept, staff was great, only thing I didn't like was the mattress needed to be replaced felt like I was sleeping in hole."
Craig 3-night trip
Posted 8 hours ago
Barefoot Beach Club

Find out more about Oldsmar

Oldsmar B&B information

Number of reviews
303
Accommodation
39 B&B
Lowest Price
CA $105
Highest Price
CA $405

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 venture out to explore Oldsmar, Tampa Bay is a some popular sight to visit.
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: 3 rooms. 13 mi (21 km) from the heart of Oldsmar. Enjoy the private yard and unique décor. The Knickerbocker by Delphius: 5 rooms. 13.8 mi (22.1 km) from the downtown core. The Kenwood Gables B&B: 5 rooms. Situated 17.6 mi (28.3 km) from the heart of Oldsmar. Enjoy the free full breakfast and patio area. Master BR private full bath,private entrance, exlusive use of pool, safe, quiet!: 9.1 mi (14.6 km) from the heart of downtown. Enjoy the in-room pools and outdoor swimming pool. Poolside Guest Suite in Mansion with Private Entrance & Bathroom. 4 Guest Max: Located 12.3 mi (19.8 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 also consider a trip to sites like Raymond James Stadium or Busch Gardens Tampa Bay 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.

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