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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Oldsmar bed & breakfast

Beach
Tampa Heights Bungalow

Tampa Heights Bungalow

Tampa Heights Bungalow
3.0 star property
Tampa Heights
9.6 out of 10, Exceptional, (155)
"Beautiful bungalow. Host was very friendly along with her wonderful dog George. Highly recommend to stay. Very close to cruise port"
United States
kimberly
The price is AED 241
AED 336 total
includes taxes & fees
21 Dec - 22 Dec
Tampa Heights Bungalow
Outdoor pool
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!

Master BR private full bath,private entrance, exlusive use of pool, safe, quiet!
Greater Northdale
9.6 out of 10, Exceptional, (66)
"Clean room and great location. "
United States
Danny M.
The price is AED 253
AED 507 total
includes taxes & fees
13 Dec - 14 Dec
Master BR private full bath,private entrance, exlusive use of pool, safe, quiet!
Interior
PRIVATE STUDIO NEAR BUSCH GARDENS

PRIVATE STUDIO NEAR BUSCH GARDENS

PRIVATE STUDIO NEAR BUSCH GARDENS
University
The price is AED 179
AED 401 total
includes taxes & fees
15 Dec - 16 Dec
PRIVATE STUDIO NEAR BUSCH GARDENS
Terrace/patio
Las Olas of Treasure Island #5

Las Olas of Treasure Island #5

Las Olas of Treasure Island #5
2.0 star property
Sunshine Beach
The price is AED 374
AED 683 total
includes taxes & fees
15 Dec - 16 Dec
Las Olas of Treasure Island #5
Outdoor dining
Diamond room 2

Diamond room 2

Diamond room 2
Citrus Park
The price is AED 228
AED 536 total
includes taxes & fees
1 Jan - 2 January 2026
Diamond room 2
Lobby sitting area
The Kenwood Gables Boutique Bed & Breakfast

The Kenwood Gables Boutique Bed & Breakfast

The Kenwood Gables Boutique Bed & Breakfast
3.5 star property
Historic Kenwood
10.0 out of 10, Exceptional, (40)
"What a great property run by a great team providing excellent service. I cannot wait to go back."
United States
Joseph
The price is AED 804
AED 908 total
includes taxes & fees
4 Jan - 5 January 2026
The Kenwood Gables Boutique Bed & Breakfast
Terrace/patio
Las Olas of Treasure Island #3

Las Olas of Treasure Island #3

Las Olas of Treasure Island #3
Sunshine Beach
9.4 out of 10, Exceptional, (3)
"Bath a little small but ok"
United States
Wade C.
Las Olas of Treasure Island #3
Terrace/patio
Cabanas of Treasure Island #4

Cabanas of Treasure Island #4

Cabanas of Treasure Island #4
Sunshine Beach
Cabanas of Treasure Island #4
Terrace/patio
Las Olas of Treasure Island #7

Las Olas of Treasure Island #7

Las Olas of Treasure Island #7
Sunshine Beach
The price is AED 370
AED 679 total
includes taxes & fees
11 Jan - 12 January 2026
Las Olas of Treasure Island #7
Terrace/patio
Las Olas of Treasure Island #9

Las Olas of Treasure Island #9

Las Olas of Treasure Island #9
Sunshine Beach
10.0 out of 10, Exceptional, (1)
"Worked great for us!"
United States
Amy M.
Las Olas of Treasure Island #9
Terrace/patio
Las Olas of Treasure Island #8

Las Olas of Treasure Island #8

Las Olas of Treasure Island #8
Sunshine Beach
The price is AED 407
AED 720 total
includes taxes & fees
14 Dec - 15 Dec
Las Olas of Treasure Island #8
Terrace/patio
Las Olas of Treasure Island No 2

Las Olas of Treasure Island No 2

Las Olas of Treasure Island No 2
Sunshine Beach
Las Olas of Treasure Island No 2
Terrace/patio
Las Olas of Treasure Island No. 10

Las Olas of Treasure Island No. 10

Las Olas of Treasure Island No. 10
Sunshine Beach
Las Olas of Treasure Island No. 10
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

Hotel South Tampa & Suites

Hotel South Tampa & Suites

10/10 Excellent
"Great room, very clean! The staff were super friendly."
Dominic Christian 4-night trip
Posted 1 day ago
Hotel South Tampa & Suites

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 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. Master BR private full bath,private entrance, exlusive use of pool, safe, quiet!: Situated 9.1 mi (14.6 km) from the heart of Oldsmar. Enjoy the in-room pools and outdoor swimming pool. Private bedroom and private bath at separate end of home with water views.: 13.5 mi (21.6 km) from the heart of downtown. PRIVATE STUDIO NEAR BUSCH GARDENS: Located 13.2 mi (21.3 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 Port of Tampa 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.