Vacation Rentals with Private Pool in South Island, FL: Compare 10+ Sites & Save

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

  4.  Florida
  5.  Fort Myers
  6.  South Island

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662 Best Vacation Rentals with Private Pool in South Island (Starting from $133)

Southern Comfort - Updated Waterfront Condo
Southern Comfort - Updated Waterfront Condo
Apartment
Fort Myers Beach, FL, USA
2.2k from South Island center

Apartments, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Condos

1 Bedroom4 Guests
New to Booking
$422
Average price / night
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2BR – Penthouse, Pool, Beach & Water Views
2BR – Penthouse, Pool, Beach & Water Views
Apartment
Fort Myers Beach, FL, 33931, United States
0.1k from South Island center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
New to Booking
$155
Average price / night
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Lovers Key Resort Suite 10 - Majestic Bay Views
Lovers Key Resort Suite 10 - Majestic Bay Views
Apartment
Fort Myers Beach, FL, USA
2.2k from South Island center

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

1 Bedroom2 Guests
New to Booking
$403
Average price / night
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Waterfront Condo- Balcony, Community Pool, Dock+ Canal Access
Waterfront Condo- Balcony, Community Pool, Dock+ Canal Access
Condo
Fort Myers Beach, FL, 33931, United States
0.1k from South Island center

AC, Balcony, Elevator, Extra Bed, Heater, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
7.8

Good

12 reviews

$246
Average price / night
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Nature View #2
Nature View #2
Apartment
Fort Myers Beach, USA
5.7k from South Island center

Barbecue/Outdoor Cooking, Fireplace/Heating, Security/Safety, Parking, Pool, Private Pool, Internet

1 Bedroom4 Guests
8.9

Fabulous

7 reviews

$352
Average price / night
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Santa Maria Resort 2/2 Canal Front
Santa Maria Resort 2/2 Canal Front
Condo
Fort Myers Beach, FL, 33931, United States
0.2k from South Island center

Balcony, Barbecue, Dryer, Elevator, Free Parking, Internet, No Smoking, Pool, TV

2 Bedrooms4 Guests
New to Booking
$318
Average price / night
Check Availability
New Build walkable to dinner, LIVE music & 5 minute walk to BEACH
New Build walkable to dinner, LIVE music & 5 minute walk to BEACH
House
Fort Myers Beach, FL, USA
6.7k from South Island center

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

3 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$659
Average price / night
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Florida Beach Spacious Luxury condo
Florida Beach Spacious Luxury condo
Condo
Fort Myers Beach, FL, 33931, United States
0.2k from South Island center

Kitchen, No Smoking, Pool

3 Bedrooms6 Guests
New to Booking
$212
Average price / night
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Nature View #3
Nature View #3
House
Fort Myers Beach, FL, USA
7.6k from South Island 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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Nice 3 BR, 2 bath Condo. Large heated pool!
Nice 3 BR, 2 bath Condo. Large heated pool!
Condo
Fort Myers Beach, FL, 33931, United States
0.2k from South Island center

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

3 Bedrooms6 Guests
9.8

Exceptional

28 reviews

$386
Average price / night
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Your Paradise Awaits: Discover sun, sand, and serenity on Estero Island.
Your Paradise Awaits: Discover sun, sand, and serenity on Estero Island.
Condo
Fort Myers Beach, FL, 33931-6700, United States
0.2k from South Island center

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

2 Bedrooms6 Guests
10.0

Exceptional

27 reviews

$294
Average price / night
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Luxury Beach Condo Located On The Bay In A Tropical Oasis!!!
Luxury Beach Condo Located On The Bay In A Tropical Oasis!!!
Condo
Fort Myers Beach, FL, 33931, United States
0.2k from South Island center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
9.8

Exceptional

13 reviews

$167
Average price / night
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Canal-front Condo w. Balcony + Hot Tub and Pool Access- Near Beach
Canal-front Condo w. Balcony + Hot Tub and Pool Access- Near Beach
Condo
Fort Myers Beach, FL, 33931, United States
0.2k from South Island center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Free Parking, Heater, Hot Tub

2 Bedrooms6 Guests
8.0

Good

1 reviews

$232
Average price / night
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Santa Maria 311 in Fort Myers Beach
Santa Maria 311 in Fort Myers Beach
Condo
Fort Myers Beach, FL, 33931, United States
0.3k from South Island center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Free Parking, Heater, Hot Tub

1 Bedroom4 Guests
9.6

Exceptional

12 reviews

$240
Average price / night
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Santa Maria 2 bedroom, 2 bathroom, water view, walk to beach
Santa Maria 2 bedroom, 2 bathroom, water view, walk to beach
Condo
Fort Myers Beach, FL, 33931, United States
0.3k from South Island center

Balcony, Barbecue, Dryer, Elevator, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$255
Average price / night
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Time to exhale. Sunrise from the balcony, and sunsets from the screened Lanai
Time to exhale. Sunrise from the balcony, and sunsets from the screened Lanai
Condo
Fort Myers Beach, FL, 33931, United States
0.3k from South Island center

AC, Arcade, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Free Parking, Heater

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$140
Average price / night
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Bella Lago 423 | Waterfront Condo with Sunroom, Pool, Hot Tub + Beach Access
Bella Lago 423 | Waterfront Condo with Sunroom, Pool, Hot Tub + Beach Access
Condo
Fort Myers Beach, FL, 33931, United States
0.3k from South Island center

AC, Balcony, Barbecue, Extra Bed, Fitness Equipment, Heater, Hot Tub, Kitchen, Laundry

2 Bedrooms4 Guests
8.0

Good

5 reviews

$275
Average price / night
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Ft. Myers Beach <br>7 minute walk to beach<br>Ft. Myers Beach .
Ft. Myers Beach <br>7 minute walk to beach<br>Ft. Myers Beach .
Condo
Fort Myers Beach, FL, 33931, United States
0.3k from South Island center

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

2 Bedrooms4 Guests
New to Booking
$215
Average price / night
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✨Amazing Bay Views + Amenities-Windward Point 507✨
✨Amazing Bay Views + Amenities-Windward Point 507✨
Condo
Fort Myers Beach, FL, 33931, United States
0.3k from South Island center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Kitchen

1 Bedroom3 Guests
New to Booking
$174
Average price / night
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401 Palm Harbor Condo of Fort Myers Beach
401 Palm Harbor Condo of Fort Myers Beach
Condo
Fort Myers Beach, FL, 33931, United States
0.4k from South Island center

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

3 Bedrooms6 Guests
9.8

Exceptional

8 reviews

$245
Average price / night
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Santa Maria Resort- Great Resort and Condo!!  Large pool/Hot Tub & Tiki Hut !!
Santa Maria Resort- Great Resort and Condo!! Large pool/Hot Tub & Tiki Hut !!
Condo
Fort Myers Beach, FL, 33931, United States
0.4k from South Island center

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

3 Bedrooms8 Guests
7.8

Good

11 reviews

$262
Average price / night
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Beautiful condo just steps from the Gulf of Mexico
Beautiful condo just steps from the Gulf of Mexico
Condo
Fort Myers Beach, FL, 33931, United States
0.4k from South Island center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$255
Average price / night
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Modern and updated 2-bedroom waterfront condo in Fort Myers Beach with pool
Modern and updated 2-bedroom waterfront condo in Fort Myers Beach with pool
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$146
Average price / night
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Beachfront Escape 708A: Gulf Views, Pool, Tennis, Beach Gear | Sleeps 4  - weekly stays
Beachfront Escape 708A: Gulf Views, Pool, Tennis, Beach Gear | Sleeps 4 - weekly stays
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

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

1 Bedroom4 Guests
10.0

Exceptional

4 reviews

$192
Average price / night
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Beachfront Estero Beach & Tennis 708C | Gulf-View Balcony | Sleeps 4 | Resort Amenities
Beachfront Estero Beach & Tennis 708C | Gulf-View Balcony | Sleeps 4 | Resort Amenities
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

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

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$189
Average price / night
Check Availability
Stunning 1-bedroom condo on enjoyable Fort Myers Beach with AC
Stunning 1-bedroom condo on enjoyable Fort Myers Beach with AC
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

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

1 Bedroom4 Guests
New to Booking
$187
Average price / night
Check Availability
Estero Beach and Tennis 1202
Estero Beach and Tennis 1202
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

Balcony, Barbecue, Dryer, Elevator, Free Parking, Internet, No Smoking, Pool, Tennis Court

1 Bedroom2 Guests
9.0

Fabulous

2 reviews

$133
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 Private Pool in South Island.

Stay Near South Island's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

South Island Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 662 verified vacation rentals with a private pool in South Island. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in South Island vary depending on the property size, location, and travel season. Rates typically start from around $133 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in South Island also welcome pets. Currently, 6 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in South Island often include additional features such as Pool, Private Pool, and Balcony/Terrace. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in South Island include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.