Bailey Hall Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Bailey Hall Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Haley's at The Anna Maria Island Inn
Save 100% on your flight
Price was $1,081, price is now $707 per person
$707
per person
Dec 5 - Dec 11
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this 3-star apartment in Holmes Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Anna Maria Beach and Bean Point Beach are located nearby.
voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
Price was $1,204, price is now $722 per person
$722
per person
Dec 5 - Dec 11
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Stay at this 3.5-star business-friendly hotel in Sarasota. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.
The Residences at Siesta Key Beach by Hyatt Vacation Club
South Village
Save 100% on your flight
Price was $2,158, price is now $1,305 per person
$1,305
per person
Dec 5 - Dec 11
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free breakfast, free WiFi, and free valet parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Tropic Isle at Anna Maria Island Inn
Save 100% on your flight
Price was $1,759, price is now $1,100 per person
$1,100
per person
Dec 5 - Dec 11
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this 4-star hotel in Bradenton Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Coquina Beach and Bean Point Beach are located nearby.
Pelican Post at Anna Maria Island Inn
Save 100% on your flight
Price was $1,450, price is now $915 per person
$915
per person
Dec 5 - Dec 11
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this 3-star apartment in Bradenton Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Coquina Beach and Bean Point Beach are located nearby.
Bali Hai Beachfront Resort and Spa
Save 100% on your flight
Price was $1,509, price is now $989 per person
$989
per person
Dec 5 - Dec 11
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this 3.5-star beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Anna Maria Beach and Bean Point Beach are located nearby.
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Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
11.09 km from Bailey Hall
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
Tropical Beach Resorts
6717 Sara Sea Circle, Siesta Key, FL
4.75 km from Bailey Hall
Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff ...
Spark by Hilton Sarasota Siesta Key Gateway
6600 S Tamiami Trl, Sarasota, FL
4.76 km from Bailey Hall
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Tropical Breeze Resort
140 Columbus Blvd., Siesta Key, FL
0.91 km from Bailey Hall
Stay at this 3-star beach hotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in ...
The Westin Sarasota
100 Marina View Drive, Sarasota, FL
6.07 km from Bailey Hall
Stay at this 4-star spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our ...
Carlisle Inn
3727 Bahia Vista, Sarasota, FL
7.96 km from Bailey Hall
Stay at this 3.5-star hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West, Bradenton, FL
26.78 km from Bailey Hall
Stay at this 4-star hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
Golden Host Resort - Sarasota
4675 N Tamiami Trl, Sarasota, FL
10.05 km from Bailey Hall
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the bar in our ...
DoubleTree by Hilton Sarasota Bradenton Airport
8009 15th Street E, Sarasota, FL
12.8 km from Bailey Hall
Stay at this 4-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hyatt Place Sarasota/Bradenton Airport
950 University Parkway, Sarasota, FL
10.91 km from Bailey Hall
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Extended Stay America Premier Suites - Bradenton
4550 53rd Ave E, Bradenton, FL
18.86 km from Bailey Hall
Stay at this hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mall at University Town Center and Rosedale Golf and ...
Comfort Suites Sarasota - Siesta Key
5690 Honore Ave, Sarasota, FL
9.68 km from Bailey Hall
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Anna Maria Beach Resort
6306 Gulf Dr, Holmes Beach, FL
29.81 km from Bailey Hall
Stay at this 3.5-star beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sun, Nov 9 - Fri, Nov 14
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days ago
Mon, Nov 10 - Mon, Nov 17
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Tue, Nov 4 - Thu, Nov 6
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$165 Roundtrip, found 2 days ago
$165
Roundtrip
found 2 days ago
Fri, Nov 7 - Thu, Nov 13
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$173 Roundtrip, found 4 days ago
$173
Roundtrip
found 4 days ago
Sat, Feb 28 - Sat, Mar 7
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$277 Roundtrip, found 4 days ago
$277
Roundtrip
found 4 days ago