95+ Vacation Rentals Near Times Square |
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Castle In Hawaii - Vacation Rentals in Times Square

"ParrotEyes FMB" North Island Beauty! Pvt Heated Pool, TOTAL RENOVATION From US $490
         

10.0 (152 Reviews)
Villa
"ParrotEyes FMB" North Island Beauty! Pvt Heated Pool, TOTAL RENOVATION
  • Air Conditioner
  • Parking
  • Pool

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Estero Island Beach Villas 401, 2 Bedrooms, Beach Front, WiFi, Sleeps 6 From US $642
         

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New
Apartment
Estero Island Beach Villas 401, 2 Bedrooms, Beach Front, WiFi, Sleeps 6
  • Air Conditioner
  • Pool
  • View

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Pink Shell Beach Resort and Marina From US $400
         

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9.4 (1234 Reviews)
Resort
Pink Shell Beach Resort and Marina
  • Air Conditioner
  • Pool
  • TV

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Island Villa with 33 Foot Infinity Pool, Dock and Boat Access, Dolphin Visits From US $355
         

10.0 (62 Reviews)
Villa
Island Villa with 33 Foot Infinity Pool, Dock and Boat Access, Dolphin Visits
  • Air Conditioner
  • Parking
  • Pool

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Gateway Villa 796, 2 Bedrooms, Sleeps 6, 7th Floor, Gulf Front, Heated Pool From US $330
         

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7.7 (3 Reviews)
Apartment
Gateway Villa 796, 2 Bedrooms, Sleeps 6, 7th Floor, Gulf Front, Heated Pool
  • Air Conditioner
  • Pool
  • View

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Casa Playa Beach Resort From US $390
         

9.4 (140 Reviews)
Resort
Casa Playa Beach Resort
  • Air Conditioner
  • Parking
  • Pool

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Seaside Villa Aqua luxury 4-bedroom villa in Fort Myers Beach incredible view From US $770
         

10.0 (3 Reviews)
Villa
Seaside Villa Aqua luxury 4-bedroom villa in Fort Myers Beach incredible view
  • Air Conditioner
  • Parking
  • Pool

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Estero Island Beach Villas 304, Sleeps 6, 2 Bedrooms, Gulf Front, Heated Pool From US $277
         

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New
Apartment
Estero Island Beach Villas 304, Sleeps 6, 2 Bedrooms, Gulf Front, Heated Pool
  • Air Conditioner
  • Parking
  • Pool

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DiamondHead Beach Resort From US $349
         

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9.2 (1026 Reviews)
Resort
DiamondHead Beach Resort
  • Air Conditioner
  • Parking
  • Pool

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Palmview Villa New 2025 One bedroom One bath! 55+ Resort Fort Myers Beach Weekly From US $141
         

New
Villa
Palmview Villa New 2025 One bedroom One bath! 55+ Resort Fort Myers Beach Weekly
  • Air Conditioner
  • Parking
  • Pool

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Tropical Romantic Getaway Steps Away from Sand w/Exclusive Beach Club Access From US $417
         

10.0 (22 Reviews)
Resort
Tropical Romantic Getaway Steps Away from Sand w/Exclusive Beach Club Access
  • Air Conditioner
  • Parking
  • Pool

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Sun-Kissed Beach Resort w/Spectacular Sunset Views - 3 Units From US $1,553
         

10.0 (1 Review)
Resort
Sun-Kissed Beach Resort w/Spectacular Sunset Views - 3 Units
  • Air Conditioner
  • Parking
  • Pool

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Welcoming Beach Hideaway Perfect for Sunny Relaxation From US $518
         

9.0 (12 Reviews)
Resort
Welcoming Beach Hideaway Perfect for Sunny Relaxation
  • Air Conditioner
  • Parking
  • Pool

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1BR unit at Windward Passage Resort From US $2,230
         

New
Resort
1BR unit at Windward Passage Resort
  • Air Conditioner
  • Parking
  • Pool

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Beach Bliss: Enjoy 4 Spacious Rooms w/Sunset & Ocean Views Nearby From US $2,077
         

New
Resort
Beach Bliss: Enjoy 4 Spacious Rooms w/Sunset & Ocean Views Nearby
  • Air Conditioner
  • Parking
  • Pool

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Watch the Waves in 4 Oceanfront Rooms with Balcony, Pool & Spa Amenities From US $1,759
         

New
Resort
Watch the Waves in 4 Oceanfront Rooms with Balcony, Pool & Spa Amenities
  • Air Conditioner
  • Parking
  • Pool

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4 Pet-Friendly Rooms with Balcony & Outdoor Pool Near Crescent Beach Park From US $1,657
         

New
Resort
4 Pet-Friendly Rooms with Balcony & Outdoor Pool Near Crescent Beach Park
  • Air Conditioner
  • Parking
  • Pool

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4 Oceanfront Rooms w/Outdoor Pool, Firepits + Near Fort Myers Beach From US $1,657
         

New
Resort
4 Oceanfront Rooms w/Outdoor Pool, Firepits + Near Fort Myers Beach
  • Air Conditioner
  • Parking
  • Pool

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3 Family-Friendly Rooms | Sun, Shops & Surf | Walk to Pier + Relax by the Pool From US $1,320
         

New
Resort
3 Family-Friendly Rooms | Sun, Shops & Surf | Walk to Pier + Relax by the Pool
  • Air Conditioner
  • Parking
  • Pool

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3 Family-Friendly Rooms | Outdoor Swimming Pool + Steps to Fort Myers Beach Pier From US $1,243
         

New
Resort
3 Family-Friendly Rooms | Outdoor Swimming Pool + Steps to Fort Myers Beach Pier
  • Air Conditioner
  • Parking
  • Pool

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Sun, Sand & Pool Views in 3 Beachfront Rooms Near Crescent Beach Family Park From US $1,243
         

New
Resort
Sun, Sand & Pool Views in 3 Beachfront Rooms Near Crescent Beach Family Park
  • Air Conditioner
  • Parking
  • Pool

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Gorgeous Beach Retreat w/Private Balcony & Outdoor Swimming Pool | 2 Rooms From US $1,061
         

New
Resort
Gorgeous Beach Retreat w/Private Balcony & Outdoor Swimming Pool | 2 Rooms
  • Air Conditioner
  • Parking
  • Pool

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2 Vibrant Rooms with Outdoor Pool & Balcony Near Crescent Beach Park From US $1,061
         

New
Resort
2 Vibrant Rooms with Outdoor Pool & Balcony Near Crescent Beach Park
  • Air Conditioner
  • Parking
  • Pool

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2 Oceanview Resort Stays w/Live Entertainment & Bar - Parking From US $1,035
         

New
Resort
2 Oceanview Resort Stays w/Live Entertainment & Bar - Parking
  • Air Conditioner
  • Parking
  • Pool

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★ Pro Tip: Castleinhawaii makes it easy to compare the best listings on Castleinhawaii homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Castleinhawaii homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Times Square.

Weather in Times Square

View the weather forecast for Times Square before booking your Times Square Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Times Square, FL

Castleinhawaii offers a large selection of top attractions around Times Square. Research things to do on your vacation before you visit Times Square.


Barefoot Beach Florida Gulf Coast University Bonita Springs Public Beach Coconut Point Mall Sanibel Island Southern Beach Hertz Arena Fishing Pier Fort Myers Beach Bowman's Beach Gulf Coast Town Center Sanibel Island Lighthouse Bell Tower Shops Miromar Outlets Fort Myers Country Club CenturyLink Sports Complex Bonita Beach Park Sanibel Island Golf Club San Carlos Island Bunche Beach Florida Southwestern State College Tanger Outlets

Times Square Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Times Square?

There are a lot of options in Times Square. If you plan on staying in the Times Square area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Times Square:

How many vacation rentals are available in Times Square?

Currently, the total number of properties listed in 2026 is over 95 in the Times Square area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Times Square.