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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.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Price was $683, price is now $464 per person
$464
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip 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 St. Armands Circle and Lido Beach are located nearby.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $857, price is now $532 per person
$532
per person
Jun 10 - Jun 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Safety Harbor. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions BayCare Ballpark and Philippe Park are located nearby.
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $1,634, price is now $1,025 per person
$1,025
per person
May 7 - May 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this 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 reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,756, price is now $1,140 per person
$1,140
per person
May 9 - May 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.
Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort

3 out of 5
Save 100% on your flight
Price was $2,253, price is now $1,490 per person
$1,490
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this beach aparthotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,294, price is now $858 per person
$858
per person
May 7 - May 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Save 100% on your flight
Price was $1,114, price is now $755 per person
$755
per person
May 31 - Jun 7
found 13 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, 3 outdoor pools, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.
Embassy Suites by Hilton Sarasota, FL

Embassy Suites by Hilton Sarasota, FL

3.5 out of 5
Save 100% on your flight
Price was $1,441, price is now $985 per person
$985
per person
May 7 - May 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.

Winter Haven Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $665, price is now $435 per person
$435
per person
Apr 30 - May 4
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Price was $683, price is now $464 per person
$464
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,328, price is now $935 per person
$935
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,112, price is now $799 per person
$799
per person
Apr 27 - May 1
found 1 day 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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $857, price is now $532 per person
$532
per person
Jun 10 - Jun 15
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,824, price is now $1,093 per person
$1,093
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,196, price is now $722 per person
$722
per person
May 23 - May 30
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,601, price is now $1,028 per person
$1,028
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)

Top Flight Deals

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

Frontier Airlines
Mon, Apr 13 - Thu, Apr 16
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$78 Roundtrip, just found
$78
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Apr 13 from Philadelphia Intl. to Tampa Intl., returning Thu, Apr 16, priced at $78 just found
Frontier Airlines
Tue, Aug 4 - Tue, Aug 18
CLE
Hopkins Intl.
TPA
Tampa Intl.
$111 Roundtrip, found 3 hours ago
$111
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, Aug 4 from Hopkins Intl. to Tampa Intl., returning Tue, Aug 18, priced at $111 found 3 hours ago
Frontier Airlines
Sat, Apr 25 - Mon, May 4
ORD
O'Hare Intl.
TPA
Tampa Intl.
$119 Roundtrip, just found
$119
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Apr 25 from O'Hare Intl. to Tampa Intl., returning Mon, May 4, priced at $119 just found
Frontier Airlines
Fri, Apr 3 - Fri, Apr 10
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$122 Roundtrip, found 1 hour ago
$122
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Apr 3 from Detroit Metropolitan Wayne County to Tampa Intl., returning Fri, Apr 10, priced at $122 found 1 hour ago