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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.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Price was $726, price is now $342 per person
$342
per person
Feb 13 - Feb 16
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this spa resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Saddlebrook Golf Course and KRATE Shopping Center are located nearby.
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Save 100% on your flight
Price was $1,141, price is now $519 per person
$519
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this spa vacation home in Tampa. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Seminole Hard Rock Casino Tampa and Port of Tampa are located nearby.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $1,023, price is now $493 per person
$493
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Family Home Tampa

Family Home Tampa

2 out of 5
Price was $1,373, price is now $681 per person
$681
per person
Mar 15 - Mar 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Stay at this guesthouse in Tampa. Enjoy free WiFi, free parking, and a garden. Popular attractions Busch Gardens Tampa Bay and Raymond James Stadium are located nearby.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,306, price is now $766 per person
$766
per person
Mar 17 - Mar 23
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 Lido Beach and St. Armands Circle are located nearby.
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $2,292, price is now $1,357 per person
$1,357
per person
Mar 17 - Mar 23
found 1 day ago
Roundtrip 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.
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 $860, price is now $539 per person
$539
per person
Mar 4 - Mar 9
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this business-friendly hotel in Lake Wales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions LEGOLAND® Florida and Eagle Ridge Mall are located nearby.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,899, price is now $1,205 per person
$1,205
per person
Mar 17 - Mar 23
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 Lido Beach and Siesta Key Beach are located nearby.

Winter Haven Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Safety Harbor - Clearwater NE by IHG

Candlewood Suites Safety Harbor - Clearwater NE by IHG

2.5 out of 5
Save 100% on your flight
Price was $465, price is now $282 per person
$282
per person
Feb 20 - Feb 23
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was $726, price is now $342 per person
$342
per person
Feb 13 - Feb 16
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Palm River-Clair Mel
Save 100% on your flight
Price was $867, price is now $452 per person
$452
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $813, price is now $497 per person
$497
per person
Mar 5 - Mar 8
found 1 day 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.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Save 100% on your flight
Price was $968, price is now $478 per person
$478
per person
Feb 24 - Mar 1
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Palm River-Clair Mel
Save 100% on your flight
Price was $1,141, price is now $519 per person
$519
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $1,023, price is now $493 per person
$493
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
Family Home Tampa

Family Home Tampa

2 out of 5
Forest Hills
Price was $1,373, price is now $681 per person
$681
per person
Mar 15 - Mar 21
found 1 day 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.

Frontier Airlines
Tue, Jan 20 - Thu, Feb 5
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$68 Roundtrip, found 15 hours ago
$68
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Tue, Jan 20 from Philadelphia Intl. to Tampa Intl., returning Thu, Feb 5, priced at $68 found 15 hours ago
Frontier Airlines
Thu, Jan 22 - Thu, Jan 29
ORD
O'Hare Intl.
TPA
Tampa Intl.
$72 Roundtrip, found 1 day ago
$72
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jan 22 from O'Hare Intl. to Tampa Intl., returning Thu, Jan 29, priced at $72 found 1 day ago
Frontier Airlines
Sat, Feb 14 - Tue, Feb 24
CLE
Hopkins Intl.
TPA
Tampa Intl.
$83 Roundtrip, found 3 days ago
$83
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Feb 14 from Hopkins Intl. to Tampa Intl., returning Tue, Feb 24, priced at $83 found 3 days ago
Spirit Airlines
Tue, Feb 3 - Wed, Feb 11
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$84 Roundtrip, found 2 days ago
$84
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Feb 3 from Detroit Metropolitan Wayne County to Tampa Intl., returning Wed, Feb 11, priced at $84 found 2 days ago