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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.
Arvilla

Arvilla

2 out of 5
Save 100% on your flight
Price was $518, price is now $345 per person
$345
per person
Feb 20 - Feb 22
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. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $733, price is now $440 per person
$440
per person
Feb 11 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Safety Harbor. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Philippe Park and Chi Chi Rodriguez Golf Club are located nearby.
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was $1,845, price is now $1,124 per person
$1,124
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a private beach, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $1,396, price is now $867 per person
$867
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach hotel in St. Pete Beach. Enjoy 2 outdoor pools, a beach locale, and a nightclub. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Pass-a-Grille Beach are located nearby.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $846, price is now $541 per person
$541
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip non-stop 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 Lido Beach and St. Armands Circle are located nearby.
BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney

3.5 out of 5
Price was $787, price is now $510 per person
$510
per person
Feb 7 - Feb 14
found 1 hour ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Stay at this vacation home in Winter Haven. Enjoy free WiFi, free parking, and a garden. Popular attractions LEGOLAND® Florida and Bartow Airbase History Museum are located nearby.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,914, price is now $1,242 per person
$1,242
per person
Feb 12 - Feb 19
found 1 day 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.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,939, price is now $1,278 per person
$1,278
per person
Feb 7 - Feb 13
found 24 hours 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.

Winter Haven Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Lake Wales N-Winter Haven by IHG

Holiday Inn Express Lake Wales N-Winter Haven by IHG

2.5 out of 5
Save 100% on your flight
Price was $546, price is now $326 per person
$326
per person
Feb 20 - Feb 24
found 15 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $733, price is now $440 per person
$440
per person
Feb 11 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $1,396, price is now $867 per person
$867
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,364, price is now $1,501 per person
$1,501
per person
Mar 3 - Mar 7
found 21 hours ago
Roundtrip non-stop 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.
The Beach Haven Resort

The Beach Haven Resort

2 out of 5
Save 100% on your flight
Price was $855, price is now $486 per person
$486
per person
Jan 29 - Feb 3
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $981, price is now $548 per person
$548
per person
Jan 29 - Feb 3
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was $1,845, price is now $1,124 per person
$1,124
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was $1,532, price is now $934 per person
$934
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip 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.

Frontier Airlines
Wed, Jan 21 - Fri, Feb 6
TTN
Mercer
TPA
Tampa Intl.
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jan 21 from Mercer to Tampa Intl., returning Fri, Feb 6, priced at $58 found 1 day ago
Frontier Airlines
Sun, Mar 1 - Wed, Mar 4
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Mar 1 from Philadelphia Intl. to Tampa Intl., returning Wed, Mar 4, priced at $58 found 1 day ago
Frontier Airlines
Sun, Jan 25 - Thu, Jan 29
ORD
O'Hare Intl.
TPA
Tampa Intl.
$59 Roundtrip, found 1 day ago
$59
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Jan 25 from O'Hare Intl. to Tampa Intl., returning Thu, Jan 29, priced at $59 found 1 day ago
Spirit Airlines
Tue, Jan 13 - Tue, Jan 27
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$59 Roundtrip, found 14 hours ago
$59
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Tue, Jan 13 from Detroit Metropolitan Wayne County to Tampa Intl., returning Tue, Jan 27, priced at $59 found 14 hours ago