Search Deals on
Winter Haven Vacation Packages

Build your package with 2 more options

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
Save 100% on your flight
Price was $303, price is now $198 per person
$198
per person
Sep 5 - Sep 8
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 St. Armands Circle and Lido Beach are located nearby.
Very nice staff. Very clean.

Reviewed on Jul 19, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,020, price is now $590 per person
$590
per person
Sep 5 - Sep 8
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 Bean Point Beach and Anna Maria Beach are located nearby.
Loved this property. Perfect place for a quiet vacation. Sits right on the beach and the views were amazing. The owner and staff were very nice. Booked through Expedia and it was a little expensive but would stay there again.

Reviewed on Jul 17, 2026

CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $779, price is now $455 per person
$455
per person
Oct 13 - Oct 17
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 Clearwater Beach and Pier 60 Park are located nearby.
Excellent

Reviewed on Jul 19, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,258, price is now $743 per person
$743
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 so nice! We had an issue with a shower not draining and they had someone there to fix it within 20 mins. It was a great experience. The only gripe is the $85 per day pet fee. I understand a resort fee but the pet fee being that much is wild.

Reviewed on Jul 19, 2026

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $690, price is now $428 per person
$428
per person
Oct 13 - Oct 17
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.
Thanks. Great Location

Reviewed on Jul 19, 2026

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,608, price is now $999 per person
$999
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach aparthotel in Clearwater Beach. Enjoy a beach locale, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Just the parking fee is expensive I paid like almost 300 for two cars in 2 days

Reviewed on Jul 17, 2026

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $909, price is now $584 per person
$584
per person
Oct 13 - Oct 17
found 1 day 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 Clearwater Beach and Pier 60 Park are located nearby.

The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
Price was $937, price is now $625 per person
$625
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a marina, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Fort De Soto Park and John's Pass Village & Boardwalk are located nearby.

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 $690, price is now $428 per person
$428
per person
Oct 13 - Oct 17
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 $1,020, price is now $590 per person
$590
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $779, price is now $455 per person
$455
per person
Oct 13 - Oct 17
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 $1,258, price is now $743 per person
$743
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)

Winter Haven Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Save 100% on your flight
Price was $1,359, price is now $820 per person
$820
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was $2,207, price is now $1,152 per person
$1,152
per person
Sep 6 - Sep 13
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
Save 100% on your flight
Price was $1,481, price is now $832 per person
$832
per person
Aug 29 - Sep 5
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
CW Hotel

CW Hotel

4 out of 5
Save 100% on your flight
Price was $1,628, price is now $963 per person
$963
per person
Oct 5 - Oct 12
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, Sep 23 - Wed, Sep 30
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$58 Roundtrip, found 5 hours ago
$58
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Sep 23 from Detroit Metropolitan Wayne County to Tampa Intl., returning Wed, Sep 30, priced at $58 found 5 hours ago
Frontier Airlines
Mon, Oct 12 - Thu, Nov 5
TTN
Mercer
TPA
Tampa Intl.
$76 Roundtrip, found 2 hours ago
$76
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Oct 12 from Mercer to Tampa Intl., returning Thu, Nov 5, priced at $76 found 2 hours ago
Frontier Airlines
Mon, Oct 12 - Thu, Nov 5
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$76 Roundtrip, found 2 hours ago
$76
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Oct 12 from Philadelphia Intl. to Tampa Intl., returning Thu, Nov 5, priced at $76 found 2 hours ago
Allegiant Air
Thu, Oct 15 - Thu, Nov 5
TTN
Mercer
PIE
St. Petersburg-Clearwater Intl.
$78 Roundtrip, found 5 hours ago
$78
Roundtrip
found 5 hours ago
Select Allegiant Air flight, departing Thu, Oct 15 from Mercer to St. Petersburg-Clearwater Intl., returning Thu, Nov 5, priced at $78 found 5 hours ago