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Winter Haven Vacation Packages

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Winter Haven Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $765, price is now $485 per person
$485
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $3,254, price is now $1,951 per person
$1,951
per person
Dec 25 - Jan 1
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.
Property was great. Loved the location. On the quieter side but close to everything

Reviewed on Oct 13, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,491, price is now $894 per person
$894
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Siesta Key Inn

Siesta Key Inn

2 out of 5
Save 100% on your flight
Price was $1,571, price is now $1,031 per person
$1,031
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Siesta Key. Enjoy free WiFi, free parking, and a garden. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Great place to stay close to the beach. The apartment is fully equipped, very clean, new appliances. Excellent communication! I definitely recommend this place, you won’t be disappointed.

Reviewed on Oct 16, 2026

Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,611, price is now $1,729 per person
$1,729
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bradenton Beach and Anna Maria Beach are located nearby.
We loved the Anna Maria Beach Resort and plan on returning for another vacation!

Reviewed on Oct 15, 2026

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $824, price is now $553 per person
$553
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

CW Resort

CW Resort

4 out of 5
Save 100% on your flight
Price was $1,183, price is now $797 per person
$797
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $942, price is now $637 per person
$637
per person
Nov 27 - Dec 2
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach hotel in Clearwater Beach. Enjoy a full-service spa, 3 restaurants, and a beach locale. Our guests praise the breakfast and the pool in our reviews. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
Clean room nice friendly staff and great atmosphere.

Reviewed on Oct 17, 2026

Winter Haven Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $765, price is now $485 per person
$485
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,491, price is now $894 per person
$894
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,795, price is now $1,183 per person
$1,183
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,212, price is now $1,480 per person
$1,480
per person
Dec 4 - Dec 8
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)

Winter Haven 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 $1,427, price is now $867 per person
$867
per person
Nov 27 - Dec 2
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $3,254, price is now $1,951 per person
$1,951
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Siesta Key Inn

Siesta Key Inn

2 out of 5
South Village
Save 100% on your flight
Price was $1,571, price is now $1,031 per person
$1,031
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
La Tortuga Historic Downtown Pass A Grille

La Tortuga Historic Downtown Pass A Grille

4 out of 5
Pass-a-Grille
Save 100% on your flight
Price was $1,599, price is now $1,055 per person
$1,055
per person
Jan 5 - Jan 11
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)

Top Flight Deals

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

Allegiant Air
Mon, Jan 11 - Fri, Jan 15
PHL
Philadelphia Intl.
PIE
St. Petersburg-Clearwater Intl.
$78 Roundtrip, found 4 hours ago
$78
Roundtrip
found 4 hours ago
Select Allegiant Air flight, departing Mon, Jan 11 from Philadelphia Intl. to St. Petersburg-Clearwater Intl., returning Fri, Jan 15, priced at $78 found 4 hours ago
Frontier Airlines
Tue, Nov 17 - Sun, Dec 6
CLE
Hopkins Intl.
TPA
Tampa Intl.
$98 Roundtrip, found 1 hour ago
$98
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Hopkins Intl. to Tampa Intl., returning Sun, Dec 6, priced at $98 found 1 hour ago
Frontier Airlines
Tue, Dec 1 - Fri, Dec 4
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$110 Roundtrip, found 4 hours ago
$110
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Dec 1 from Detroit Metropolitan Wayne County to Tampa Intl., returning Fri, Dec 4, priced at $110 found 4 hours ago
Frontier Airlines
Tue, Nov 17 - Wed, Dec 2
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$116 Roundtrip, found 4 hours ago
$116
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Philadelphia Intl. to Tampa Intl., returning Wed, Dec 2, priced at $116 found 4 hours ago