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

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  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Fort Myers
  6.  Times Square

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2783 Best Vacation Rentals with Pool in Times Square (Starting from $164)

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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Tropical Romantic Getaway Steps Away from Sand w/ Exclusive Beach Club Access
Tropical Romantic Getaway Steps Away from Sand w/ Exclusive Beach Club Access
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

1 Bedroom2 Guests
9.8

Exceptional

24 reviews

$347
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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Welcoming Beach Hideaway Perfect for Sunny Relaxation
Welcoming Beach Hideaway Perfect for Sunny Relaxation
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

1 Bedroom4 Guests
9.4

Superb

18 reviews

$356
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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2 Oceanview Resort Stays w/ Live Entertainment & Bar - Parking
2 Oceanview Resort Stays w/ Live Entertainment & Bar - Parking
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

2 Bedrooms8 Guests
New to Booking
$714
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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Sun-Kissed Beach Resort w/ Spectacular Sunset Views - 3 Units
Sun-Kissed Beach Resort w/ Spectacular Sunset Views - 3 Units
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

3 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$1071
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 Bliss: Enjoy 4 Spacious Rooms w/ Sunset & Ocean Views Nearby
Beach Bliss: Enjoy 4 Spacious Rooms w/ Sunset & Ocean Views Nearby
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

4 Bedrooms16 Guests
New to Booking
$1424
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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2 Vibrant Rooms with Outdoor Pool & Balcony Near Crescent Beach Park
2 Vibrant Rooms with Outdoor Pool & Balcony Near Crescent Beach Park
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

2 Bedrooms4 Guests
New to Booking
$692
Average price / night
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Nature View #3
Nature View #3
House
Fort Myers Beach, FL, USA
0.3k from Times Square center

Barbecue/Outdoor Cooking, Security/Safety, Parking, Pool, Private Pool, Internet, Air Conditioner

1 Bedroom4 Guests
7.8

Good

18 reviews

$164
Average price / night
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Gorgeous Beach Retreat w/ Private Balcony & Outdoor Swimming Pool | 2 Rooms
Gorgeous Beach Retreat w/ Private Balcony & Outdoor Swimming Pool | 2 Rooms
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

2 Bedrooms4 Guests
New to Booking
$692
Average price / night
Check Availability
Harbour House at the Inn Unit 211 condo
Harbour House at the Inn Unit 211 condo
Apartment
Fort Myers Beach, FL, USA
0.3k from Times Square center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Jacuzzis, Places to stay

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$341
Average price / night
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Sun, Sand & Pool Views in 3 Beachfront Rooms Near Crescent Beach Family Park
Sun, Sand & Pool Views in 3 Beachfront Rooms Near Crescent Beach Family Park
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

3 Bedrooms6 Guests
New to Booking
$1039
Average price / night
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Harbour House at the Inn Unit 213 condo
Harbour House at the Inn Unit 213 condo
Apartment
Fort Myers Beach, FL, USA
0.3k from Times Square center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Family, Beach rentals

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$179
Average price / night
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3 Family-Friendly Rooms | Outdoor Swimming Pool + Steps to Fort Myers Beach Pier
3 Family-Friendly Rooms | Outdoor Swimming Pool + Steps to Fort Myers Beach Pier
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

3 Bedrooms6 Guests
New to Booking
$1038
Average price / night
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Premier Island Escape
Premier Island Escape
House
Fort Myers Beach, FL, USA
0.4k from Times Square center

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

2 Bedrooms6 Guests
8.5

Very Good

2 reviews

$643
Average price / night
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4 Oceanfront Rooms w/ Outdoor Pool, Firepits + Near Fort Myers Beach
4 Oceanfront Rooms w/ Outdoor Pool, Firepits + Near Fort Myers Beach
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

4 Bedrooms8 Guests
New to Booking
$1384
Average price / night
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Beautiful New Build - 450 Palermo home
Beautiful New Build - 450 Palermo home
House
Fort Myers Beach, FL, USA
0.4k from Times Square center

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

4 Bedrooms10 Guests
New to Booking
$946
Average price / night
Check Availability
4 Pet-Friendly Rooms with Balcony & Outdoor Pool Near Crescent Beach Park
4 Pet-Friendly Rooms with Balcony & Outdoor Pool Near Crescent Beach Park
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

4 Bedrooms8 Guests
New to Booking
$1383
Average price / night
Check Availability
Tropical Poolside Stay w/ Outdoor Pool and Ocean Views Near Fort Myers Beach
Tropical Poolside Stay w/ Outdoor Pool and Ocean Views Near Fort Myers Beach
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

1 Bedroom2 Guests
New to Booking
$347
Average price / night
Check Availability
Stay on the Beach w/ Outdoor Pool Access + Firepits & Dining
Stay on the Beach w/ Outdoor Pool Access + Firepits & Dining
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

1 Bedroom4 Guests
New to Booking
$357
Average price / night
Check Availability
2 Welcoming Rooms | Steps from Times Square & Pier | Pool, Spa + Beachfront
2 Welcoming Rooms | Steps from Times Square & Pier | Pool, Spa + Beachfront
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

2 Bedrooms8 Guests
New to Booking
$714
Average price / night
Check Availability
3 Family-Friendly Rooms | Sun, Shops & Surf | Walk to Pier + Relax by the Pool
3 Family-Friendly Rooms | Sun, Shops & Surf | Walk to Pier + Relax by the Pool
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

3 Bedrooms12 Guests
New to Booking
$1071
Average price / night
Check Availability
Watch the Waves in 4 Oceanfront Rooms with Balcony, Pool & Spa Amenities
Watch the Waves in 4 Oceanfront Rooms with Balcony, Pool & Spa Amenities
Resort
Fort Myers Beach, FL, 33931, United States
0.1k from Times Square center

AC, Balcony, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Pool

4 Bedrooms16 Guests
New to Booking
$1423
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 with Pool in Times Square.

Where to stay in Times Square? Best neighborhoods & areas

Times Square Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 2783 verified vacation rentals with a pool in Times Square. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Times Square vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $164 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Times Square offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Times Square welcome pets. Currently, 15 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Times Square often include additional outdoor features such as Pool, Accessibility, and Wheelchair Accessible. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Times Square offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.