Search Deals onMadeira Beach Vacation Packages
Madeira Beach Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key
Save 100% on your flight
Price was $688, price is now $436 per person
$436
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly aparthotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Cedar Cove Resort and Cottages
Save 100% on your flight
Price was $2,082, price is now $1,242 per person
$1,242
per person
Dec 8 - Dec 15
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
voco Sarasota by IHG
Save 100% on your flight
Price was $1,452, price is now $936 per person
$936
per person
Dec 8 - Dec 15
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 Lido Beach and Siesta Key Beach are located nearby.
It was very comfortable.
I love the fact you have transportation to go to the beach and that you gave us the umbrella, towels and chairs.
The front desk personnel were very nice and helpful.
Thanks
Reviewed on Sep 23, 2026
The Avalon Club
Save 100% on your flight
Price was $1,412, price is now $925 per person
$925
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this aparthotel in Clearwater Beach. Enjoy a fitness center, parking (surcharge), and in-room massages. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Our family had a wonderful stay. The location was perfect. We also loved being able to use the hotels umbrellas, chairs & towels at the beach. The suite was more spacious than we expected! The sofa bed was not comfortable, but the regular beds were. Can’t beat the price for the room & view we had. We would absolutely come back!
Reviewed on Sep 21, 2026
Seaside at Anna Maria Island Inn
Save 100% on your flight
Price was $3,066, price is now $2,034 per person
$2,034
per person
Dec 8 - Dec 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach hotel in Bradenton Beach. Enjoy a beach locale, daily housekeeping, and cable TV channels. Popular attractions Coquina Beach and Bradenton Beach are located nearby.
Great place to stay! Friendly staff and beautiful ocean front rooms.
Reviewed on Sep 18, 2026
Ocean Club Treasure Island Hotel
Save 100% on your flight
Price was $1,497, price is now $999 per person
$999
per person
Dec 16 - Dec 21
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.
It was very nice. My husband is ready to return
Reviewed on Sep 23, 2026
VIinoy House
Save 100% on your flight
Price was $1,230, price is now $826 per person
$826
per person
Nov 9 - Nov 15
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Stay at this B&B in St. Petersburg. Enjoy free WiFi, free parking, and bathrobes. Popular attractions Tampa Bay and Vinoy Park are located nearby.
CW Resort
Save 100% on your flight
Price was $992, price is now $674 per person
$674
per person
Dec 3 - Dec 8
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.
Madeira Beach Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Madeira Beach Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Oct 2 - Mon, Oct 5
PHL
Philadelphia Intl.
PIE
St. Petersburg-Clearwater Intl.
$98 Roundtrip, found 5 days ago
$98
Roundtrip
found 5 days ago
Tue, Nov 17 - Wed, Dec 2
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$111 Roundtrip, found 13 hours ago
$111
Roundtrip
found 13 hours ago
Mon, Oct 26 - Fri, Oct 30
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$112 Roundtrip, found 12 hours ago
$112
Roundtrip
found 12 hours ago
Tue, Oct 20 - Wed, Oct 28
MSP
Minneapolis - St. Paul Intl.
TPA
Tampa Intl.
$117 Roundtrip, found 3 days ago
$117
Roundtrip
found 3 days ago
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