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

Book Oldsmar Bed & Breakfast

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

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

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
$124 nightly
The price is $138
Sep 28 - Sep 29
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, (212 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
$73 nightly
The price is $83
Sep 30 - Oct 1
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.
$181 nightly
The price is $202
Sep 28 - Sep 29
Total with taxes and fees
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
$299 nightly
The price is $339
Sep 28 - Sep 29
Total with taxes and fees
The Knickerbocker by Delphius
A cozy lounge area with a neon sign, plush seating, and potted plants.

5. 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.
$146 nightly
The price is $162
Sep 28 - Sep 29
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.

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.
$152 nightly
The price is $169
Sep 29 - Sep 30
Total with taxes and fees
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.
$187 nightly
The price is $208
Sep 28 - Sep 29
Total with taxes and fees
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
$250 nightly
The price is $282
Oct 28 - Oct 29
Total with taxes and fees
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.
$199 nightly
The price is $222
Sep 30 - Oct 1
Total with taxes and fees
The 1888 Hotel (Casita) 2Bed/1Bath Detached
A cozy lounge area with a neon sign, plush seating, and potted plants.

10. The 1888 Hotel (205) Honeymoon King Studio

The 1888 Hotel (205) Honeymoon King Studio
Downtown St. Petersburg
$170 nightly
The price is $190
Oct 4 - Oct 5
Total with taxes and fees
The 1888 Hotel (205) Honeymoon King Studio
A cozy lounge area with a neon sign, plush seating, and potted plants.

11. 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.
$146 nightly
The price is $162
Sep 28 - Sep 29
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.

12. 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
Sep 29 - Sep 30
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.

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
Sep 29 - Sep 30
Total with taxes and fees
Las Olas of Treasure Island #7
A cozy lounge area with a neon sign, plush seating, and potted plants.

14. The 1888 Hotel (206) Queen Studio Suite

The 1888 Hotel (206) Queen Studio Suite
Downtown St. Petersburg
$146 nightly
The price is $162
Sep 28 - Sep 29
Total with taxes and fees
The 1888 Hotel (206) Queen Studio Suite
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
Sep 29 - Sep 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 (102) ADA

The 1888 Hotel (102) ADA
Downtown St. Petersburg
$146 nightly
The price is $162
Sep 28 - Sep 29
Total with taxes and fees
The 1888 Hotel (102) ADA
A modern outdoor lounge area with sun loungers, a covered seating area, and a canopy bed.

17. 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 1 - Oct 2
Total with taxes and fees
Las Olas of Treasure Island #3
A cozy lounge area with a neon sign, plush seating, and potted plants.

18. The 1888 Hotel (305) Honeymoon King Studio

The 1888 Hotel (305) Honeymoon King Studio
Downtown St. Petersburg
$157 nightly
The price is $175
Sep 28 - Sep 29
Total with taxes and fees
The 1888 Hotel (305) Honeymoon King Studio
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.
$160 nightly
The price is $179
Oct 4 - Oct 5
Total with taxes and fees
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
$175 nightly
The price is $195
Sep 28 - Sep 29
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oldsmar Hotel Reviews

Mint House St. Petersburg Downtown by Kasa

Mint House St. Petersburg Downtown by Kasa

10/10 Excellent
"The best fairly priced place I’ve ever stayed! The pool was the perfect temperature."
Kaitlyn 2-night trip
Posted 12 hours ago
Mint House St. Petersburg Downtown by Kasa

Find out more about Oldsmar

Oldsmar B&B information

Number of reviews
305
Accommodation
48 B&B
Lowest Price
$83
Highest Price
$339

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 $83 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.

Explore a world of travel with Expedia