Bailey Hall Vacations
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- Mar Bay Motel &Suites
Aug 16 - Aug 21Mar Bay Motel &Suites + Flight
Safety Harbor5 nights8.6/10 - Excellent (79 reviews)"Great for older people who want an easily accessible room in a quiet setting. We will be back!"Reviewed May 7, 2026Roundtrip • New York (EWR) - Tampa (TPA)EWR - TPA • 1 stop TPA - JFK • 1 stop - Cedar Cove Resort and Cottages
Aug 6 - Aug 10Cedar Cove Resort and Cottages + Flight
Holmes Beach4 nights9.2/10 - Wonderful (517 reviews)"It was amazing, we stayed at the Flamingo Suite, all was clean and tidy. The cottage has a great location close to all restaurants either south or north of the island since it is situated kind of in the middle of the island. The staff was so nice and understanding. So conveniently located right on the beach. Overall a great experience."Reviewed May 25, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • Nonstop$1,227$770found 1 day agoper traveler - Landing St. Petersburg Near South Branch Potomac River
Aug 8 - Aug 15Landing St. Petersburg Near South Branch Potomac River + Flight
St. Petersburg7 nightsRoundtrip • Trenton (TTN) - Tampa (TPA)TTN - TPA • Nonstop TPA - TTN • Nonstop - The Westin Sarasota
Aug 15 - Aug 22The Westin Sarasota + Flight
Central Sarasota7 nights9.0/10 - Wonderful (1,195 reviews)"We had a wonderful stay! The hotel was very clean, comfortable, and well-maintained. The staff was friendly, welcoming, and always willing to help with anything we needed. The room was spotless, the beds were comfortable, and the overall atmosphere made us feel relaxed from the moment we arrived. We truly enjoyed our stay and would definitely return in the future. Highly recommend!"Reviewed May 25, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • Nonstop$1,133$762found 1 day agoper traveler - The Residences at Siesta Key Beach by Hyatt Vacation Club
Aug 13 - Aug 16The Residences at Siesta Key Beach by Hyatt Vacation Club + Flight
South Village3 nights9.6/10 - Exceptional (353 reviews)"Our room was very clean and very nice with a great layout. The beach was beautiful, but unfortunately we booked late, so beach views weren't available. We faced the front of the hotel which was a poor view. The complimentary breakfast was not good and unavailable or late opening 2 of the 7 days we were there. I requested a discount due to this and they did give me one. There were resort fees added on that was not disclosed by Expedia and not in our initial total. They removed the beach..."Reviewed May 25, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • Nonstop$2,124$1,429found 1 day agoper traveler
Where to stay in Bailey Hall
Find the best Bailey Hall areas and neighborhoods for the activities you enjoy most. Learn more about Bailey Hall
Siesta Key Village
1 out of top 10 points of interest in this area
4.5/5(283 area reviews)
Tropical colored buildings, lots of sandy beaches and a compact shopping area make this village a good choice to visit and stay. Enjoy an on-going social life too.
Bailey Hall Hotel Deals
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from May 27 to May 28
$114 total
May 27 - May 28
Total with taxes and fees
9.2/10 Wonderful! (5,419 reviews)
"The bathroom setup in the rooms was not convenient for families traveling with older kids."
Reviewed on May 26, 2026
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $229 total per night from Jun 1 to Jun 2
$229 total
Jun 1 - Jun 2
Total with taxes and fees
9.4/10 Exceptional! (2,187 reviews)
"Facility and room were in like new condition though the property is over 6 years old. Decor/furnishings were tasteful. Property well maintained and functioning. Front desk staff often seemed bored or disinterested. Not too helpful. The coffee, breakfast bar and snack station in Lobby were not well ..."
Reviewed on May 25, 2026
Golden Host Resort - Sarasota
4675 N Tamiami Trl Sarasota FL
Fully refundable
$75 nightly
The price is $85 total per night from May 31 to Jun 1
$85 total
May 31 - Jun 1
Total with taxes and fees
8.6/10 Excellent! (2,517 reviews)
"The place was so tranquil and fun stuff was wonderful. Definitely a place to check out."
Reviewed on May 26, 2026
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.