Bailey Hall Vacations from $381
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Bailey Hall Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Residences at Siesta Key Beach by Hyatt Vacation Club
South Village
Save 100% on your flight
Price was $2,735, price is now $1,506 per person
$1,506
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
9.6/10 Exceptional! (294 reviews)
Suite 601 is an exceptional ocean front room with views of sunrise and sunset. The room has top notch appliances and was sparkling clean!
Reviewed on Nov 24, 2025
Kompose Boutique Hotel
Save 100% on your flight
Price was $1,183, price is now $667 per person
$667
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (4,624 reviews)
The room was really nice! Comparable to other modern boutique hotels we've stayed at in Europe, except this one is more spacious. Friendly, attentive staff. Great price! Thank you!
Reviewed on Dec 4, 2025
Compass Hotel by Margaritaville Anna Maria Sound
Save 100% on your flight
Price was $762, price is now $431 per person
$431
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
9.4/10 Exceptional! (1,843 reviews)
Prooerty was very clean. Staff were very friendly and able to answerr questions. Pool is amazing and very clean.
Reviewed on Dec 3, 2025
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(282 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
$78 nightly
The price is $88 total per night from Dec 9 to Dec 10
$88 total
Dec 9 - Dec 10
Total with taxes and fees
9/10 Wonderful! (4,748 reviews)
Beautiful hotel with well kept rooms. Immaculate pool and hot tub area with ping pong, fire, and other activities. Great breakfast, friendly staff. WELL worth your money.
Reviewed on Dec 2, 2025
Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $148 total per night from Dec 7 to Dec 8
$148 total
Dec 7 - Dec 8
Total with taxes and fees
9.2/10 Wonderful! (5,129 reviews)
Courteous staff. Nice room, short stroll to beach for sunset.
Reviewed on Dec 3, 2025
Carlisle Inn
3727 Bahia Vista Sarasota FL
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $192 total per night from Dec 8 to Dec 9
$192 total
Dec 8 - Dec 9
Total with taxes and fees
9.8/10 Exceptional! (2,131 reviews)
Everything was perfect.
Reviewed on Dec 2, 2025
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.