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Island Players Vacation Packages

Island Players Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Save 100% on your flight
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Book a stay at this golf 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.
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Stay at this 4-star historic hotel in Tampa. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tampa Riverwalk and Port of Tampa are located nearby.
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Raymond James Stadium and Tampa Riverwalk are located nearby.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Nov 22 - Nov 28
found 13 hours ago
Roundtrip flight included
Raleigh (RDU) to Sarasota (SRQ)
Stay at this 3-star beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Bradenton Beach and Coquina Beach are located nearby.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
per person
Nov 22 - Nov 28
found 15 hours ago
Roundtrip flight included
Raleigh (RDU) to Tampa (TPA)
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and St. Armands Circle are located nearby.
Captiva Beach Resort

Captiva Beach Resort

2 out of 5
Save 100% on your flight
per person
Nov 22 - Nov 28
found 15 hours ago
Roundtrip flight included
Raleigh (RDU) to Sarasota (SRQ)
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
per person
Nov 22 - Nov 28
found 15 hours ago
Roundtrip flight included
Raleigh (RDU) to Tampa (TPA)
Book a stay at this business-friendly aparthotel in Sarasota. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Save 100% on your flight
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy free parking, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Raymond James Stadium and Tampa Riverwalk are located nearby.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Nov 2 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to Tampa (TPA)
Stay at this 4-star 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.
SPOT X Hotel Tampa Bay by The Red Collection

SPOT X Hotel Tampa Bay by The Red Collection

3 out of 5
Save 100% on your flight
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Stay at this 3-star business-friendly hotel in Wesley Chapel. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions KRATE Shopping Center and The Grove at Wesley Chapel are located nearby.
Siesta Palms By the Beach

Siesta Palms By the Beach

3.5 out of 5
Save 100% on your flight
per person
Nov 22 - Nov 28
found 13 hours ago
Roundtrip flight included
Raleigh (RDU) to Sarasota (SRQ)
Stay at this 3.5-star aparthotel in Siesta Key. Enjoy free WiFi, free parking, and a garden. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Holiday Inn Tampa Westshore - Airport Area, an IHG Hotel

Holiday Inn Tampa Westshore - Airport Area, an IHG Hotel

3 out of 5
Save 100% on your flight
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Stay at this 3-star business-friendly hotel in Tampa. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Raymond James Stadium and Tampa Riverwalk are located nearby.

3-4 Night Vacations in Island Players

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
Save 100% on your flight
per person
Nov 8 - Nov 11
found 20 hours ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Downtown Tampa
Save 100% on your flight
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Beach Park
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)

5-7 Night Vacations in Island Players

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Wesley Chapel South
Save 100% on your flight
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Downtown Tampa
Save 100% on your flight
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
Save 100% on your flight
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Nov 22 - Nov 28
found 13 hours ago
Roundtrip flight included
Raleigh (RDU) to Sarasota (SRQ)

Book the perfect getaway to Island Players

With Hotwire, booking your next trip to Anna Maria is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Island Players while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Island Players flight and hotel package for as low as $386.

Living it up in Anna Maria means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Island Players, Anna Maria vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Island Players for some of the best accommodations and flight deals.

FAQs about cheap Island Players packages:

How to get cheap vacation deals to Island Players?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as .

How much are Island Players packages?

Vacation packages to Island Players vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $386.

How to find cheap car rentals near Island Players?

Hotwire partners with some of the most reliable car rental companies in Anna Maria to bring you the best car rental deals in Island Players for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Island Players now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Island Players right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.