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Longboat Key Vacation Packages

Build your package with 2 more options

Longboat Key Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was $1,006, price is now $603 per person
$603
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this golf hotel in Bradenton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Coquina Beach and IMG Golf Academy are located nearby.

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,336, price is now $793 per person
$793
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bradenton Beach and Coquina Beach are located nearby.
What a treat for us Minnesotans!!! Special place to stay. Clean, comfy, and cozy! We stayed in the Violet Cottage. Staff allowed us to hang for a bit on the beach (plus parking for our rental) after check-out. There is even a shower available for this exact purpose, which is extra handy and appreciated. Thank you! We hope to be back some day!

Reviewed on Nov 9, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,146, price is now $684 per person
$684
per person
Jan 11 - Jan 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
Nice property, clean pool. Units were not sound roof at all, you could hear every little noise from each room and other units, but it did not ruin our time there.

Reviewed on Nov 10, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $1,057, price is now $654 per person
$654
per person
Feb 3 - Feb 7
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this 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 St. Armands Circle and Lido Beach are located nearby.

Crystal Palms Beach Resort

Crystal Palms Beach Resort

3.5 out of 5
Price was $1,207, price is now $751 per person
$751
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this aparthotel in Treasure Island. Enjoy a 24-hour front desk, dry cleaning or laundry services, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
It was amazing I felt like I got a whole apartment In one . It’s literally across the street from the beach 2-5 min walk you can see the water from hotel. It has a pool and hot tub .Everything was clean, the check in to get the keys in a lock box was different but I didn’t mind it . It felt like top secret underground location lol. 15/10 rating

Reviewed on Nov 7, 2026

Stylish Treasure Island Escape

Stylish Treasure Island Escape

3 out of 5
Price was $6,437, price is now $4,077 per person
$4,077
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Stay at this apartment in Treasure Island. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

CW Resort

CW Resort

4 out of 5
Price was $1,431, price is now $907 per person
$907
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.

The Roth Hotel

The Roth Hotel

2 out of 5
Price was $1,349, price is now $855 per person
$855
per person
Jan 24 - Jan 31
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Treasure Island. Enjoy free WiFi, free parking, and a free beach shuttle. Our guests praise the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Sunset Beach Pavilion are located nearby.
Truly a treasure!!! Don’t miss the opportunity to stay here. Love the proximity to the beach. The dock was so tranquil and great for sipping coffee in the mornings and my son loved to fish and watch for dolphins & manatees!

Reviewed on Sep 12, 2026

Longboat Key Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was $921, price is now $530 per person
$530
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $1,336, price is now $793 per person
$793
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Price was $1,006, price is now $603 per person
$603
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Price was $1,057, price is now $654 per person
$654
per person
Feb 3 - Feb 7
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)

Longboat Key Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,146, price is now $684 per person
$684
per person
Jan 11 - Jan 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Crystal Palms Beach Resort

Crystal Palms Beach Resort

3.5 out of 5
Sunshine Beach
Price was $1,207, price is now $751 per person
$751
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was $1,532, price is now $964 per person
$964
per person
Jan 24 - Jan 31
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stylish Treasure Island Escape

Stylish Treasure Island Escape

3 out of 5
Sunshine Beach
Price was $6,437, price is now $4,077 per person
$4,077
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Delta
Tue, Feb 2 - Sat, Feb 6
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$209 Roundtrip, found 4 hours ago
$209
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Feb 2 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Sat, Feb 6, priced at $209 found 4 hours ago
Delta
Tue, Jan 19 - Tue, Feb 2
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$209 Roundtrip, just found
$209
Roundtrip
just found
Select Delta flight, departing Tue, Jan 19 from LaGuardia to Sarasota-Bradenton Intl., returning Tue, Feb 2, priced at $209 just found
Delta
Tue, Jan 5 - Sat, Jan 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$219 Roundtrip, found 1 hour ago
$219
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jan 5 from Logan Intl. to Sarasota-Bradenton Intl., returning Sat, Jan 9, priced at $219 found 1 hour ago
Delta
Sun, Dec 20 - Sat, Dec 26
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$289 Roundtrip, found 1 hour ago
$289
Roundtrip
found 1 hour ago
Select Delta flight, departing Sun, Dec 20 from Hartsfield-Jackson Atlanta Intl. to Sarasota-Bradenton Intl., returning Sat, Dec 26, priced at $289 found 1 hour ago