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Winter Haven Vacation Packages

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Winter Haven
Florida
United States of America
North America
Hotwire.com

Winter Haven Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

ChartHouse Clearwater Beach Marina Hotel

2 out of 5

Save 100% on your flight

Price was $357, price is now $206 per person

$206

per person

Sep 15 - Sep 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)

Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a rooftop terrace, and a 24-hour fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.

Ocean Club Treasure Island Hotel

4 out of 5

Save 100% on your flight

Price was $1,521, price is now $815 per person

$815

per person

Sep 9 - Sep 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.

Everything was great. The beds are not the most comfortable, but we were fine

Reviewed on Aug 9, 2026

Cedar Cove Resort and Cottages

3 out of 5

Price was $1,095, price is now $602 per person

$602

per person

Sep 24 - Sep 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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 Coquina Beach and Bean Point Beach are located nearby.

Todo muy limpio

Reviewed on Aug 9, 2026

CW Hotel

4 out of 5

Price was $1,628, price is now $992 per person

$992

per person

Oct 15 - Oct 22

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.

Twin Palms at Siesta

3 out of 5

Save 100% on your flight

Price was $474, price is now $296 per person

$296

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)

Book a stay at this beach hotel in Siesta Key. Enjoy free WiFi, free parking, and private pools. Our guests praise the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Cómoda limpia y bien equipada Muy tranquila el sector

Reviewed on Aug 2, 2026

The Westin Sarasota

4 out of 5

Price was $1,311, price is now $827 per person

$827

per person

Oct 17 - Oct 23

found 23 hours 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.

Todo muy bien

Reviewed on Aug 9, 2026

Saddlebrook Resort

4 out of 5

Save 100% on your flight

Price was $889, price is now $567 per person

$567

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)

Book a stay at this golf resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and 3 restaurants. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Saddlebrook Golf Course and KRATE Shopping Center are located nearby.

Very nice and quiet, staff were helpful, will come back

Reviewed on Aug 8, 2026

Holiday Inn Tampa North by IHG

3 out of 5

Save 100% on your flight

Price was $537, price is now $350 per person

$350

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)

Book a stay at this business-friendly hotel in Tampa. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Tampa Bay and Seminole Hard Rock Casino Tampa are located nearby.

Overall, the hotel was very clean and cleaning staff was friendly when we asked them for extra towels. However, our room wasn’t cleaned on the second day when it says rooms get cleaned daily. Staff was not available at the counter on multiple occasions.

Reviewed on Aug 9, 2026