Holiday rentals near Times Square
We found 14,015 holiday rentals — enter your dates for availability
If you'd like to stay close to Times Square, scroll through and discover private holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, such as air conditioning and a TV. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Times Square
Showing deals for:7 Nov - 14 Nov
Image gallery for 1940 Luxury 6BR Home: Heated Pool, Spa, Near Beach!
8.88.8 out of 10 rating
Excellent
(6 reviews)
1940 Luxury 6BR Home: Heated Pool, Spa, Near Beach!
Fort Myers Beach, FL
6% off
Price is NZ$10,400
NZ$10,400
NZ$1,486 per night
includes taxes & fees
Image gallery for Seahorse Suites #4. A Perfect Beach Getaway!
8.08.0 out of 10 rating
Very good
(6 reviews)
Seahorse Suites #4. A Perfect Beach Getaway!
Sanibel, FL
15% off
Price is NZ$4,766
NZ$4,766
NZ$681 per night
includes taxes & fees
Image gallery for Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts
9.09.0 out of 10 rating
Wonderful
(16 reviews)
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts
Captiva, FL
7% off
Price is NZ$11,097
NZ$11,097
NZ$1,585 per night
includes taxes & fees
Image gallery for RELAX and Unwind on Fort Myers Beach in a 2BR/2BA Gorgeous Gulf views and Pool
9.89.8 out of 10 rating
Exceptional
(64 reviews)
RELAX and Unwind on Fort Myers Beach in a 2BR/2BA Gorgeous Gulf views and Pool
Fort Myers Beach, FL
8% off
Price is NZ$3,511
NZ$3,511
NZ$502 per night
includes taxes & fees
Image gallery for Toes In the Sand: 3Br/2BA with Pool,Bikes&Games- 4 min walk to Beach & Publix!
9.89.8 out of 10 rating
Exceptional
(108 reviews)
Toes In the Sand: 3Br/2BA with Pool,Bikes&Games- 4 min walk to Beach & Publix!
Fort Myers Beach, FL
8% off
Price is NZ$5,064
NZ$5,064
NZ$723 per night
includes taxes & fees
Image gallery for SANTA CLARA! Coastal, modern 3BR ESCAPE, harbor view, boat slip, CLUB access
1010 out of 10 rating
Exceptional
(6 reviews)
SANTA CLARA! Coastal, modern 3BR ESCAPE, harbor view, boat slip, CLUB access
Captiva, FL
7% off
Price is NZ$4,560
NZ$4,560
NZ$651 per night
includes taxes & fees
Image gallery for Steps from Bonita Beach! Great family home with a pool on salt water canal!
9.69.6 out of 10 rating
Exceptional
(46 reviews)
Steps from Bonita Beach! Great family home with a pool on salt water canal!
Bonita Springs, FL
8% off
Price is NZ$6,949
NZ$6,949
NZ$993 per night
includes taxes & fees
Image gallery for Relax in Paradise: 2-Bedroom Island Retreat with private Pool & Golf Cart!
1010 out of 10 rating
Exceptional
(15 reviews)
Relax in Paradise: 2-Bedroom Island Retreat with private Pool & Golf Cart!
Captiva, FL
12% off
Price is NZ$5,701
NZ$5,701
NZ$814 per night
includes taxes & fees
Image gallery for Waterfront House with Heated Pool, Jacuzzi & Private Dock
1010 out of 10 rating
Exceptional
(12 reviews)
Waterfront House with Heated Pool, Jacuzzi & Private Dock
Fort Myers, FL
16% off
Price is NZ$8,068
NZ$8,068
NZ$1,153 per night
includes taxes & fees
Image gallery for Luxurious 4100 SqFt. 5BR Poolside Home with Heated pool, 6 Beds, 12 Sleeps.
1010 out of 10 rating
Exceptional
(6 reviews)
Luxurious 4100 SqFt. 5BR Poolside Home with Heated pool, 6 Beds, 12 Sleeps.
Fort Myers, FL
11% off
Price is NZ$9,811
NZ$9,811
NZ$1,402 per night
includes taxes & fees
Image gallery for Cape Villa Family Friendly Canal front 4 Bedroom Southern Facing Heated Pool Spa
1010 out of 10 rating
Exceptional
(29 reviews)
Cape Villa Family Friendly Canal front 4 Bedroom Southern Facing Heated Pool Spa
Cape Coral, FL
8% off
Price is NZ$5,415
NZ$5,415
NZ$774 per night
includes taxes & fees
Image gallery for Waterfront home with a POOL in Cape Coral! 12 miles to Fort Myers Beach!
1010 out of 10 rating
Exceptional
(14 reviews)
Waterfront home with a POOL in Cape Coral! 12 miles to Fort Myers Beach!
Cape Coral, FL
8% off
Price is NZ$3,946
NZ$3,946
NZ$564 per night
includes taxes & fees
Image gallery for Cozy and warm 3-bedroom cottage with a pool in the island
8.28.2 out of 10 rating
Very good
(11 reviews)
Cozy and warm 3-bedroom cottage with a pool in the island
Saint James City, FL
7% off
Price is NZ$2,683
NZ$2,683
NZ$383 per night
includes taxes & fees
Image gallery for 3134 Gulf-Front 5BR: Pool, Spa, Stunning Views
9.49.4 out of 10 rating
Exceptional
(11 reviews)
3134 Gulf-Front 5BR: Pool, Spa, Stunning Views
Fort Myers Beach, FL
7% off
Price is NZ$14,661
NZ$14,661
NZ$2,094 per night
includes taxes & fees
Image gallery for Enjoy your private resort/villa on the water with incredible views and location!
9.89.8 out of 10 rating
Exceptional
(70 reviews)
Enjoy your private resort/villa on the water with incredible views and location!
Cape Coral, FL
8% off
Price is NZ$17,191
NZ$17,191
NZ$2,456 per night
includes taxes & fees
Image gallery for In the center of town and 5 minutes from everything FUN!
1010 out of 10 rating
Exceptional
(25 reviews)
In the center of town and 5 minutes from everything FUN!
Cape Coral, FL
14% off
Price is NZ$3,367
NZ$3,367
NZ$481 per night
includes taxes & fees
Image gallery for Waterfront Oasis in SW Cape Coral Florida
1010 out of 10 rating
Exceptional
(10 reviews)
Waterfront Oasis in SW Cape Coral Florida
Cape Coral, FL
11% off
Price is NZ$2,779
NZ$2,779
NZ$397 per night
includes taxes & fees
Image gallery for Santa Maria Resort- Great Resort and Condo!! Large refurbished pool & hot tub!
8.08.0 out of 10 rating
Very good
(5 reviews)
Santa Maria Resort- Great Resort and Condo!! Large refurbished pool & hot tub!
Fort Myers Beach, FL
15% off
Price is NZ$3,181
NZ$3,181
NZ$454 per night
includes taxes & fees
Image gallery for Sunrise Haven: Your Retreat in Bonita Springs 6 bedrooms/5 bath, close to Gulf
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Sunrise Haven: Your Retreat in Bonita Springs 6 bedrooms/5 bath, close to Gulf
Bonita Springs, FL
8% off
Price is NZ$8,154
NZ$8,154
NZ$1,165 per night
includes taxes & fees
Image gallery for 109 Charming Coastal Haven: Heated Pool, Walk to Beach
9.49.4 out of 10 rating
Exceptional
(9 reviews)
109 Charming Coastal Haven: Heated Pool, Walk to Beach
Fort Myers Beach, FL
6% off
Price is NZ$4,808
NZ$4,808
NZ$687 per night
includes taxes & fees
Image gallery for Dream catcher, where your dreams come true! Beachy waterfront Villa Heated pool
1010 out of 10 rating
Exceptional
(48 reviews)
Dream catcher, where your dreams come true! Beachy waterfront Villa Heated pool
Cape Coral, FL
11% off
Price is NZ$3,606
NZ$3,606
NZ$515 per night
includes taxes & fees
Image gallery for 8214 Private Beach House w/ Heated Pool & Ocean Views!
1010 out of 10 rating
Exceptional
(7 reviews)
8214 Private Beach House w/ Heated Pool & Ocean Views!
Fort Myers Beach, FL
7% off
Price is NZ$11,696
NZ$11,696
NZ$1,671 per night
includes taxes & fees
Image gallery for Western Exposure on cul-de-sac with spill over spa pool & boat dock. SUNSETS!
1010 out of 10 rating
Exceptional
(56 reviews)
Western Exposure on cul-de-sac with spill over spa pool & boat dock. SUNSETS!
Cape Coral, FL
7% off
Price is NZ$3,728
NZ$3,728
NZ$533 per night
includes taxes & fees
Image gallery for Spacious 6bdr/5bath Vacation Home 1 mi to beach
9.69.6 out of 10 rating
Exceptional
(54 reviews)
Spacious 6bdr/5bath Vacation Home 1 mi to beach
Naples, FL
8% off
Price is NZ$9,138
NZ$9,138
NZ$1,305 per night
includes taxes & fees
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Find the best place to stay - Times Square
SUMMER SPECIAL "ParrotEyes FMB" North Island Beauty! Pvt Pool, TOTAL RENOVATION
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
145 reviews(145 reviews)
New 3-bedroom home with private heated pool, steps to the beach
Sleeps 12 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Times Square Hideaway By FL Vibes
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
4 King, 2 Bath, Pool, Tiki Bar Home-1 Blk to Shops/Restaurants/Times Sq/Beach
Sleeps 10 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Beach House ~ Minutes walk to white sand Gulf of Mexico!
Sleeps 4 · 3 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
76 reviews(76 reviews)
3/2 plus a DEN, Gulf Access, and Centrally Located Heated Pool Home!
Sleeps 7 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
97 reviews(97 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value