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

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    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

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, (77 reviews)
"Second time we stayed! We enjoyed it thanks"
United States
Jennifer
$124 nightly
The price is $138
Nov 1 - Nov 2
Total with taxes and fees
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, (214 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
$84 nightly
The price is $95
Nov 16 - Nov 17
Total with taxes and fees
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.
$182 nightly
The price is $203
Oct 25 - Oct 26
Total with taxes and fees
Poolside Guest Suite in Mansion with Private Entrance & Bathroom. 4 Guest Max
A hot tub with built-in lighting, a wooden deck, and a window with a shutter.

4. The Knickerbocker by Delphius

The Knickerbocker by Delphius
3.0 star property
Hyde Park
$240 nightly
The price is $272
Oct 29 - Oct 30
Total with taxes and fees
The Knickerbocker by Delphius
A modern outdoor lounge area with sun loungers, a covered seating area, and a canopy bed.

5. Las Olas of Treasure Island #5

Las Olas of Treasure Island #5
Sunshine Beach
$152 nightly
The price is $169
Oct 25 - Oct 26
Total with taxes and fees
Las Olas of Treasure Island #5
A cozy lounge area with a neon sign, plush seating, and potted plants.

6. 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.
$152 nightly
The price is $169
Nov 2 - Nov 3
Total with taxes and fees
The 1888 Hotel (103) Queen Studio Suite
A covered outdoor seating area with wicker furniture, a central table with a lit candle, and lush greenery in the background.

7. VIinoy House

VIinoy House
3.5 star property
Historic Old Northeast
7.0 out of 10, Good, (6 reviews)
"Bed, bedding and pillows were the highlight of the stay. Very comfortable."
United States
eric
$343 nightly
The price is $387
Nov 1 - Nov 2
Total with taxes and fees
VIinoy House
A cozy lounge area with a neon sign, plush seating, and potted plants.

8. The 1888 Hotel 202 (A/B/C) 2 Bed/1 Bath King Suite

The 1888 Hotel 202 (A/B/C) 2 Bed/1 Bath King Suite
Downtown St. Petersburg
$199 nightly
The price is $222
Oct 29 - Oct 30
Total with taxes and fees
The 1888 Hotel 202 (A/B/C) 2 Bed/1 Bath King Suite
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.
$204 nightly
The price is $227
Nov 1 - Nov 2
Total with taxes and fees
The 1888 Hotel (Casita) 2Bed/1Bath Detached
A modern outdoor lounge area with sun loungers, a covered seating area, and a canopy bed.

10. 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.
$152 nightly
The price is $169
Oct 29 - Oct 30
Total with taxes and fees
Cabanas of Treasure Island #4
A modern outdoor lounge area with sun loungers, a covered seating area, and a canopy bed.

11. Las Olas of Treasure Island No. 1

Las Olas of Treasure Island No. 1
Sunshine Beach
$183 nightly
The price is $205
Nov 2 - Nov 3
Total with taxes and fees
Las Olas of Treasure Island No. 1
A modern outdoor lounge area with sun loungers, a covered seating area, and a canopy bed.

12. 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.
$152 nightly
The price is $169
Oct 26 - Oct 27
Total with taxes and fees
Las Olas of Treasure Island #3
A modern outdoor lounge area with sun loungers, a covered seating area, and a canopy bed.

13. 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.
$152 nightly
The price is $169
Oct 27 - Oct 28
Total with taxes and fees
Las Olas of Treasure Island #7
The exterior of The 1888 Hotel, featuring a classic facade with a balcony, potted plants, and a prominent entrance.

14. The 1888 Hotel (205) Honeymoon King Studio

The 1888 Hotel (205) Honeymoon King Studio
Downtown St. Petersburg
8.0 out of 10, Very good, (1 review)
"This is a nicely maintained, old hotel within walking distance to all of downtown St Pete. The suite was well equipped and very clean."
United States
JULI
$165 nightly
The price is $184
Nov 2 - Nov 3
Total with taxes and fees
The 1888 Hotel (205) Honeymoon King Studio
A modern outdoor patio with lounge chairs and a covered seating area, surrounded by palm trees and a building with a white exterior.

15. 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.
$177 nightly
The price is $198
Oct 29 - Oct 30
Total with taxes and fees
Las Olas of Treasure Island #9
A cozy lounge area with a neon sign, plush seating, and potted plants.

16. 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.
$160 nightly
The price is $179
Oct 29 - Oct 30
Total with taxes and fees
The 1888 Hotel (204) Digital Nomad Queen Suite
A modern outdoor lounge area with sun loungers, a covered seating area, and a canopy bed.

17. Las Olas of Treasure Island No. 10

Las Olas of Treasure Island No. 10
Sunshine Beach
$177 nightly
The price is $198
Oct 29 - Oct 30
Total with taxes and fees
Las Olas of Treasure Island No. 10
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.
$152 nightly
The price is $169
Nov 2 - Nov 3
Total with taxes and fees
The 1888 Hotel (306) Queen Studio Suite
A modern outdoor lounge area with sun loungers, a covered seating area, and a canopy bed.

19. 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.
$152 nightly
The price is $169
Oct 27 - Oct 28
Total with taxes and fees
Las Olas of Treasure Island #8
A modern outdoor lounge area with sun loungers, a covered seating area, and a canopy bed.

20. Las Olas of Treasure Island No 2

Las Olas of Treasure Island No 2
Sunshine Beach
$177 nightly
The price is $198
Oct 29 - Oct 30
Total with taxes and fees
Las Olas of Treasure Island No 2
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 Westshore Grand, Tampa, A Tribute Portfolio Hotel

The Westshore Grand, Tampa, A Tribute Portfolio Hotel

8/10 Good
"The rooms were pretty clean but a little old. The bar staff were amazing and front desk was helpful as well. Breakfast was gross, do not recommend. Only good thing there at the buffet was the fresh omelet."
Amber 1-night trip
Posted 12 hours ago
The Westshore Grand, Tampa, A Tribute Portfolio Hotel

Find out more about Oldsmar

Oldsmar B&B information

Number of reviews
237
Accommodation
39 B&B
Lowest Price
$95
Highest Price
$387

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 $95 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.

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