Search Deals onTimes Square Vacation Packages
Times Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites
Save 100% on your flight
per person
May 12 - May 17
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Port Charlotte. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Deep Creek Golf Club and Lake Betty Park are located nearby.
Private Pool + Sunroom Beach Escape at Manatee
Save 100% on your flight
per person
Apr 30 - May 7
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3-star cottage in Naples. Enjoy free parking, patios, and air conditioning. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
Embassy Suites by Hilton Fort Myers Estero
Save 100% on your flight
per person
May 12 - May 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3.5-star business-friendly hotel in Estero. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Hertz Arena and Coconut Point Mall are located nearby.
The Lighthouse Resort Inn & Suites
Save 100% on your flight
per person
May 12 - May 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
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 attractions Key West Express and Times Square are located nearby.
Villa Marco Island
Save 100% on your flight
per person
Apr 30 - May 7
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3.5-star beach villa in Marco Island. Enjoy free WiFi, free parking, and private pools. Popular attractions City of Marco Island Racquet Center and Marco Island Historical Museum are located nearby.
Sleep Inn & Suites Port Charlotte - Punta Gorda
per person
May 15 - May 22
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Port Charlotte. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Deep Creek Golf Club and Lake Betty Park are located nearby.
Bellasera Resort
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Green Bay (GRB) 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 Pier are located nearby.
Sanibel Island Beach Resort
Save 100% on your flight
per person
May 15 - May 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3-star beach hotel in Sanibel. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular attractions Sanibel Island Southern Beach and Sanibel Island Golf Club are located nearby.
Country Inn & Suites by Radisson, Port Charlotte, FL
per person
May 15 - May 22
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Port Charlotte. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Deep Creek Golf Club and Lake Betty Park are located nearby.
The Perry Hotel Naples
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Green Bay (GRB) to Fort Myers (RSW)
Stay at this 4.5-star luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
THE Palmview AND Sandpiper Inns
Save 100% on your flight
per person
May 12 - May 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3.5-star motel in Sanibel. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Sanibel Island Southern Beach and Sanibel Island Golf Club are located nearby.
Marco Polo by Avantstay Waterfront 5bdr, Pool, Spa, Fire Pit, Walk to Beach
Save 100% on your flight
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3-star cottage in Marco Island. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Mackle Park and Marco Island Historical Museum are located nearby.
3-4 Night Vacations in Times Square
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Times Square
Price found within the past 48 hours. Click for updated prices.
Times Square Last Minute Hotel Deals
Margaritaville Beach Resort Fort Myers
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 ...
Lani Kai Beachfront Resort
1400 Estero Blvd, Fort Myers Beach, FL
Stay at this 3.5-star beach hotel in Fort Myers Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Popular attractions Key West Express and Times Square ...
Edison Beach House
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 ...
Pink Shell Beach Resort and Marina
275 Estero Blvd, Fort Myers Beach, FL
Stay at this 4-star beach resort in Fort Myers Beach. Enjoy free breakfast, 3 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the pool ...
The Lighthouse Resort Inn & Suites
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 ...
DiamondHead Beach Resort
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 ...
Harbour House At The Inn
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 ...
Matanzas Inn Bayside Resort and Marina
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 ...
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.
Discover Other Travel Deals
- Legoland Florida
- Universal Studios Hollywood®
- Legoland California
- Broadway New York
- The Wizarding World of Harry Potter
- Sanibel Captiva Island
- Paseo de España
- Universal Studios Florida
- San Antonio SeaWorld
- Siargao Island
- Australia Zoo
- Busch Gardens Tampa Bay
- SeaWorld® Orlando
- Tolantongo Caves
- Eleuthera and Harbour Island
- Biltmore Estate
- Blue Lagoon
- Swiss Alps
- Silver Dollar City
- Lackland Air Force Base
- Grand Teton National Park
- San Diego Zoo
- Holy Land Experience
- Grand Ole Opry
- Ark Encounter
- Levi's Stadium
- Breckenridge Ski Resort
- Alcatraz Island
- Six Flags Magic Mountain
- Walt Disney World®
- Dollywood
- Kalahari Waterpark Resort
- Giza Pyramid Complex
- Casino at Don Laughlin's Riverside Resort
- Hoover Dam
- Hollywood Beach
- Faisalabad Clock Tower
- Venice Beach Boardwalk
- Blue Lagoon Beach
- Moraine Lake
- Apartment Hotel in Fort Myers Beach
- Hotels with a Pool in Fort Myers Beach
- Beach Hotels in Fort Myers Beach
- Hotels with Free Parking in Fort Myers Beach
- Family Hotels in Fort Myers Beach
- Historic Hotels in Fort Myers Beach
- Romantic Hotels in Fort Myers Beach
- Hotels with Hot Tubs in Fort Myers Beach
- Resorts & Hotels with Spas in Fort Myers Beach
- Luxury Hotels in Fort Myers Beach
- Naples Hotels
- Fort Myers Beach Hotels
- Fort Myers Hotels
- Cape Coral Hotels
- Sanibel Hotels
- Bonita Springs Hotels
- Sanibel Captiva Island Hotels
- North Naples Hotels
- Captiva Hotels
- Estero Hotels
- South Florida Hotels
- Saint James City Hotels
- North Fort Myers Hotels
- Gulf Coast Hotels
- Lehigh Acres Hotels
- Bokeelia Hotels
Hotels Near Points of Interest in Times Square
- Hotels near Key West Express
- Hotels near Florida Gulf Coast University
- Hotels near Barefoot Beach
- Hotels near Coconut Point Mall
- Hotels near Bonita Springs Public Beach
- Hotels near Hertz Arena
- Hotels near Edison Mall
- Hotels near Gulf Coast Town Center
- Hotels near Bell Tower Shops
- Hotels near Estero Boulevard Beach
- Hotels near Lee Health Sports Complex
- Hotels near Bowman's Beach
- Hotels near Bunche Beach
- Hotels near Lynn Hall Memorial Park
- Hotels near Sanibel Island Lighthouse
- Hotels near Miromar Outlets
Car Rentals in Times Square
- Car rentals in Naples
- Car rentals in Fort Myers Beach
- Car rentals in Fort Myers
- Car rentals in Cape Coral
- Car rentals in Sanibel
- Car rentals in Bonita Springs
- Car rentals in Sanibel Captiva Island
- Car rentals in North Naples
- Car rentals in Captiva
- Car rentals in Estero
- Car rentals in South Florida
- Car rentals in Saint James City
- Car rentals in North Fort Myers
- Car rentals in Gulf Coast
- Car rentals in Lehigh Acres
- Car rentals in Bokeelia
Book a Vacation to Times Square
Prices are always lower in the app!
Book and go: Last-minute deals and trip details all in one place
Exclusive prices: Hot Rate® Hotels always cost less in the app
Fresh features: So slick you’ll never go back to desktop
