Vacation Rentals in Times Square, FL: Compare 10+ Sites & Save

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  4.  Florida
  5.  Fort Myers
  6.  Times Square

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2207 Best Vacation Rentals in Times Square (Starting from $206)

Ocean Jewels 2 - Overlooks Margaritaville PoolBeach
Ocean Jewels 2 - Overlooks Margaritaville PoolBeach
Apartment
Fort Myers Beach, FL, USA
0.2k from Times Square center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$412
Average price / night
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Times Square Hideaway By FL Vibes
Times Square Hideaway By FL Vibes
Apartment
Fort Myers Beach, FL, 33931, United States
0.0k from Times Square center

AC, Balcony, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom4 Guests
9.8

Exceptional

25 reviews

$377
Average price / night
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122 Primo Dr home
122 Primo Dr home
House
Fort Myers Beach, FL, USA
0.3k from Times Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$394
Average price / night
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Sage Sands Cottage | Steps to Beach/Pool/ Fort Myers Beach Times Square
Sage Sands Cottage | Steps to Beach/Pool/ Fort Myers Beach Times Square
Cottage
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, Pool

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$284
Average price / night
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1030 Second Street home
1030 Second Street home
House
Fort Myers Beach, FL, USA
0.3k from Times Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$280
Average price / night
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Fins Right - Next to Margaritaville
Fins Right - Next to Margaritaville
Apartment
Fort Myers Beach, FL, 33931, United States
0.2k from Times Square center

AC, Barbecue, Free Parking, Internet, Living Area, Microwave, No Smoking, TV

1 Bedroom2 Guests
8.8

Fabulous

5 reviews

$231
Average price / night
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218 Primo Dr - Mermaid Beach House home
218 Primo Dr - Mermaid Beach House home
House
Fort Myers Beach, FL, USA
0.3k from Times Square center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay

2 Bedrooms6 Guests
New to Booking
$660
Average price / night
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One Particular Cottage - Next to Margaritaville
One Particular Cottage - Next to Margaritaville
Apartment
Fort Myers Beach, FL, 33931, United States
0.2k from Times Square center

AC, Balcony, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, TV

2 Bedrooms4 Guests
6.0

Review score

1 reviews

$378
Average price / night
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218 Primo Dr - Beach House home
218 Primo Dr - Beach House home
House
Fort Myers Beach, FL, USA
0.3k from Times Square center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay

3 Bedrooms12 Guests
New to Booking
$632
Average price / night
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Fins Left - Next to Margaritaville
Fins Left - Next to Margaritaville
Apartment
Fort Myers Beach, FL, 33931, United States
0.2k from Times Square center

AC, Barbecue, Free Parking, Internet, Living Area, Microwave, No Smoking, TV

1 Bedroom2 Guests
New to Booking
$226
Average price / night
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218 Primo Dr - Dolphin Beach House home
218 Primo Dr - Dolphin Beach House home
House
Fort Myers Beach, FL, USA
0.3k from Times Square center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay

2 Bedrooms6 Guests
New to Booking
$474
Average price / night
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Parrot Cottage - Margaritaville District
Parrot Cottage - Margaritaville District
Apartment
Fort Myers Beach, FL, 33931, United States
0.2k from Times Square center

AC, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$285
Average price / night
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Harbour House at the Inn Unit 205 condo
Harbour House at the Inn Unit 205 condo
Apartment
Fort Myers Beach, FL, USA
0.3k from Times Square center

Apartments, Accommodations, Pools, Parking, Lodgings, Jacuzzis, Places to stay, Condos

2 Bedrooms6 Guests
New to Booking
$490
Average price / night
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LOCATION!  LOCATION!   Charming 2-bedroom house in delightful Fort Myers Beach
LOCATION! LOCATION! Charming 2-bedroom house in delightful Fort Myers Beach
House
Fort Myers Beach, FL, 33931, United States
0.2k from Times Square center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
9.8

Exceptional

6 reviews

$224
Average price / night
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Harbour House at the Inn 302
Harbour House at the Inn 302
Apartment
Fort Myers Beach, FL, USA
0.3k from Times Square center

Apartments, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$218
Average price / night
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Beach/Pool Access Cottage - Walk to Times Square, Fort Myers Beach
Beach/Pool Access Cottage - Walk to Times Square, Fort Myers Beach
Cottage
Fort Myers Beach, FL, 33931, United States
0.2k from Times Square center

AC, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, Pool

1 Bedroom3 Guests
New to Booking
$268
Average price / night
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Docs Cottage
Docs Cottage
House
Fort Myers Beach, FL, USA
0.3k from Times Square center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$503
Average price / night
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DOWNTOWN 3rd Street Retreat Hideout — Steps to Beach
DOWNTOWN 3rd Street Retreat Hideout — Steps to Beach
Apartment
Fort Myers Beach, FL, 33931, United States
0.2k from Times Square center

AC, Dryer, Internet, Laundry, Living Area, No Smoking, Washer

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$330
Average price / night
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Seabird Cottage
Seabird Cottage
House
Fort Myers Beach, FL, USA
0.3k from Times Square center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$285
Average price / night
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Ocean Jewels 1 - Overlooks Margaritaville
Ocean Jewels 1 - Overlooks Margaritaville
Apartment
Fort Myers Beach, FL, 33931, United States
0.2k from Times Square center

AC, Balcony, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom6 Guests
10.0

Exceptional

1 reviews

$276
Average price / night
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141 Brand New Luxury 6BR 6BA Build with Heated Pool! home
141 Brand New Luxury 6BR 6BA Build with Heated Pool! home
House
Fort Myers Beach, FL, USA
0.3k from Times Square center

Luxury, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs

6 Bedrooms14 Guests
New to Booking
$1337
Average price / night
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Ocean Jewels 2 - Overlooks Margaritaville
Ocean Jewels 2 - Overlooks Margaritaville
Apartment
Fort Myers Beach, FL, 33931, United States
0.2k from Times Square center

AC, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

1 Bedroom4 Guests
8.8

Fabulous

8 reviews

$262
Average price / night
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Ocean Jewels 3 - Overlooks Margaritaville
Ocean Jewels 3 - Overlooks Margaritaville
Apartment
Fort Myers Beach, FL, 33931, United States
0.2k from Times Square center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
9.2

Superb

21 reviews

$341
Average price / night
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Steps to Beach & Local Hotspots| Cozy Cottage Cabana Azul|
Steps to Beach & Local Hotspots| Cozy Cottage Cabana Azul|
House
Fort Myers Beach, FL, 33931, United States
0.3k from Times Square center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
9.8

Exceptional

13 reviews

$206
Average price / night
Check Availability
Beach, pool time & fun times @ Blue Fish Lagoon
Beach, pool time & fun times @ Blue Fish Lagoon
Apartment
Fort Myers Beach, FL, 33931, United States
0.3k from Times Square center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$314
Average price / night
Check Availability
Beach, pool and fun times @ Blue Oyster Lagoon
Beach, pool and fun times @ Blue Oyster Lagoon
Apartment
Fort Myers Beach, FL, 33931, United States
0.3k from Times Square center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$306
Average price / night
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Cozy Condo Located in Times Square at Fort Myers Beach
Cozy Condo Located in Times Square at Fort Myers Beach
Apartment
Fort Myers Beach, FL, 33919, United States
0.3k from Times Square center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
New to Booking
$642
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Times Square.

Where to stay in Times Square? Best neighborhoods & areas

Times Square Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2207 verified vacation rentals in Times Square. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Times Square vary depending on the season, property size, and location. Rates typically start from around $206 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Times Square include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Times Square welcome pets. Currently, 20 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Times Square often include amenities such as Internet, Wellness Facilities, and Bedding/Linens. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.