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Times Square Vacation Packages

Times Square Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Swiftwater Apartments By Barsala

Swiftwater Apartments By Barsala

3.5 out of 5
Save 100% on your flight
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3.5-star aparthotel in Port Charlotte. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions North Charlotte Regional Park and Charlotte Sports Park are located nearby.
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Save 100% on your flight
per person
Jan 6 - Jan 12
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3.5-star beach condo in Fort Myers. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Key West Express and Sanibel Island Southern Beach are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this beach resort in Naples. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
Bellasera Resort

Bellasera Resort

4 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this business-friendly condo in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Fifth Avenue South and Naples Beach are located nearby.
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 4.5-star luxury resort in Naples. Enjoy 3 outdoor pools, a full-service spa, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Naples Zoo at Caribbean Gardens are located nearby.
Southseas

Southseas

3 out of 5
Save 100% on your flight
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
Stay at this 3-star beach apartment in Marco Island. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions Tigertail Beach and Sand Dollar Island Beach and Landing are located nearby.
Inn on Fifth

Inn on Fifth

4 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 4-star spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and a free beach shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Fifth Avenue South and Naples Beach are located nearby.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this beach resort in Captiva. Enjoy 2 outdoor pools, a full-service spa, and 3 restaurants. Popular attractions Captiva Beach and Captiva Chapel By the Sea are located nearby.
Coco Mango by Avantstay Chic and Private Captiva Escape

Coco Mango by Avantstay Chic and Private Captiva Escape

3 out of 5
Save 100% on your flight
per person
Jan 6 - Jan 12
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3-star cottage in Captiva. Enjoy a pool table, balconies, and in-room washers/dryers. Popular attractions McCarthy's Marina and Jungle Drums are located nearby.
Innovation Hotel

Innovation Hotel

4 out of 5
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 4-star business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Tiburon Golf Club and Vanderbilt Beach are located nearby.
Bayfront Inn Fifth Avenue

Bayfront Inn Fifth Avenue

3.5 out of 5
Save 100% on your flight
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Naples. Enjoy free WiFi, free parking, and a marina. Our guests praise the restaurant and the bar in our reviews. Popular attractions Fifth Avenue South and Naples Beach are located nearby.
Edison Beach House

Edison Beach House

3.5 out of 5
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Times Square are located nearby.

3-4 Night Vacations in Times Square

Price found within the past 48 hours. Click for updated prices.
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
Save 100% on your flight
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
Park Shore
Save 100% on your flight
per person
Jan 4 - Jan 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
per person
Jan 4 - Jan 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
per person
Jan 4 - Jan 7
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)

5-7 Night Vacations in Times Square

Price found within the past 48 hours. Click for updated prices.
Swiftwater Apartments By Barsala

Swiftwater Apartments By Barsala

3.5 out of 5
Save 100% on your flight
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Punta Rassa
Save 100% on your flight
per person
Jan 6 - Jan 12
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)

Times Square Last Minute Hotel Deals

Margaritaville Beach Resort Fort Myers
Margaritaville Beach Resort Fort Myers
4 out of 5
251 Crescent Street, Fort Myers Beach, FL
Stay at this 4-star beach hotel in Fort Myers Beach. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Margaritaville Beach Resort Fort Myers
The Lighthouse Resort Inn & Suites
The Lighthouse Resort Inn & Suites
3 out of 5
1051 5th St, Fort Myers Beach, FL
Stay at this 3-star hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the bar in our reviews. Popular ...
The Lighthouse Resort Inn & Suites
Pink Shell Beach Resort and Marina
Pink Shell Beach Resort and Marina
4 out of 5
275 Estero Blvd, Fort Myers Beach, FL
Stay at this 4-star beach resort in Fort Myers Beach. Enjoy free breakfast, 2 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the pool ...
Pink Shell Beach Resort and Marina
Edison Beach House
Edison Beach House
3.5 out of 5
830 Estero Blvd., Fort Myers Beach, FL
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff and ...
Edison Beach House
DiamondHead Beach Resort
DiamondHead Beach Resort
3.5 out of 5
2000 Estero Blvd, Fort Myers Beach, FL
Stay at this 3.5-star beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in ...
DiamondHead Beach Resort
Matanzas Inn Bayside Resort and Marina
Matanzas Inn Bayside Resort and Marina
3 out of 5
414 Crescent Street, Fort Myers Beach, FL
Stay at this 3-star hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms ...
Matanzas Inn Bayside Resort and Marina
Harbour House At The Inn
Harbour House At The Inn
3 out of 5
450 Old San Carlos Blvd, Fort Myers Beach, FL
Stay at this 3-star hotel in Fort Myers Beach. Enjoy free WiFi, a marina, and a business center. Our guests praise the clean rooms in our reviews. Popular attractions ...
Harbour House At The Inn
Latitude 26 Waterfront Boutique Resort - Fort Myers Beach
Latitude 26 Waterfront Boutique Resort - Fort Myers Beach
2.5 out of 5
17990 San Carlos Blvd, Fort Myers Beach, FL
Stay at this hotel in Fort Myers Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
Latitude 26 Waterfront Boutique Resort - Fort Myers Beach
See all 10,317 properties in Times Square
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Thu, Jan 9 - Thu, Jan 16
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$70 Roundtrip, found 10 hours ago
$70
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Thu, Jan 9 from Logan Intl. to Southwest Florida Intl., returning Thu, Jan 16, priced at $70 found 10 hours ago
Frontier Airlines
Sat, Jan 4 - Wed, Jan 8
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$83 Roundtrip, found 2 days ago
$83
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Jan 4 from Hopkins Intl. to Southwest Florida Intl., returning Wed, Jan 8, priced at $83 found 2 days ago
Frontier Airlines
Wed, Dec 18 - Tue, Dec 24
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$93 Roundtrip, found 1 day ago
$93
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Dec 18 from Philadelphia Intl. to Southwest Florida Intl., returning Tue, Dec 24, priced at $93 found 1 day ago
Frontier Airlines
Sun, Jan 12 - Sun, Jan 19
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$95 Roundtrip, found 2 days ago
$95
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Jan 12 from O'Hare Intl. to Southwest Florida Intl., returning Sun, Jan 19, priced at $95 found 2 days ago

Book the perfect getaway to Times Square

With Hotwire, booking your next trip to Downtown Fort Myers Beach 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 Times Square 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 Times Square flight and hotel package for as low as $615.

Living it up in Downtown Fort Myers Beach means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Times Square, Downtown Fort Myers Beach 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 Times Square for some of the best accommodations and flight deals.

FAQs about cheap Times Square packages:

How to get cheap vacation deals to Times Square?

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 $125.

How much are Times Square packages?

Vacation packages to Times Square 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 $615.

How to find cheap car rentals near Times Square?

Hotwire partners with some of the most reliable car rental companies in Downtown Fort Myers Beach to bring you the best car rental deals in Times Square 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 Times Square now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Times Square 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.

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