Vacation Rentals with Private Pool in Bailey's Beach, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Fort Myers
  6.  Bailey's Beach

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546 Best Vacation Rentals with Private Pool in Bailey's Beach (Starting from $164)

Marriott Sanibel Harbour Resort & Spa
Marriott Sanibel Harbour Resort & Spa
Resort
Fort Myers, FL, USA
4.5k from Bailey's Beach center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, Marriott , 4-star, Lodgings

337 Bedrooms82 Guests
7.8

Good

484 reviews

$227
Average price / night
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 Bayfront 3BR steps from San Carlos Bay-Private Fishing Pier, Dolphins, Sunsets!
Bayfront 3BR steps from San Carlos Bay-Private Fishing Pier, Dolphins, Sunsets!
Condo
Sanibel, FL, 33957, United States
0.5k from Bailey's Beach center

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

3 Bedrooms6 Guests
9.6

Exceptional

90 reviews

$489
Average price / night
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Nature View #3
Nature View #3
House
Fort Myers Beach, FL, USA
8.3k from Bailey's Beach 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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Sanibel 6 bedroom Luxury Home with Pool,One Block from Beach,Pier and Canal View
Sanibel 6 bedroom Luxury Home with Pool,One Block from Beach,Pier and Canal View
House
Sanibel, FL, 33957, United States
0.6k from Bailey's Beach center

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

6 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$565
Average price / night
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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
9.2k from Bailey's Beach 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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Pool fully remodeled in 2026!
Pool fully remodeled in 2026!
House
Sanibel, FL, 33957, United States
0.6k from Bailey's Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.8

Exceptional

64 reviews

$470
Average price / night
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Osprey Hideaway: Pet-Friendly Island Home w/ Pool!
Osprey Hideaway: Pet-Friendly Island Home w/ Pool!
House
Sanibel, FL, 33957, United States
0.7k from Bailey's Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
New to Booking
$254
Average price / night
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SeaRose- Gorgeous Sanibel Estate now with dining credit!!
SeaRose- Gorgeous Sanibel Estate now with dining credit!!
House
Sanibel, FL, 33957, United States
0.7k from Bailey's Beach center

Balcony, Barbecue, Elevator, Free Parking, Internet, Kitchen, Laundry, Living Area, No Smoking

1 Bedroom10 Guests
New to Booking
$614
Average price / night
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Exclusive Sanibel Marina Residence with Pool
Exclusive Sanibel Marina Residence with Pool
House
Sanibel, FL, 33957, United States
0.8k from Bailey's Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$211
Average price / night
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Spectacular Direct access canal front beauty!
Spectacular Direct access canal front beauty!
House
Sanibell, FL, 33957, United States
0.8k from Bailey's Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$461
Average price / night
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3 Bedroom Pool Home in The Dunes!
3 Bedroom Pool Home in The Dunes!
House
Sanibel, FL, 33957, United States
0.8k from Bailey's Beach center

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

3 Bedrooms8 Guests
New to Booking
$337
Average price / night
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Nestled along a pristine canal with long range views, this meticulously crafted residence defines coastal luxury at its finest.NEW!
Nestled along a pristine canal with long range views, this meticulously crafted residence defines coastal luxury at its finest.NEW!
House
Sanibel, FL, 33957, United States
0.9k from Bailey's Beach center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$350
Average price / night
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Bean & Bubs Shell Shack: Gorgeous PoolHome on Lake
Bean & Bubs Shell Shack: Gorgeous PoolHome on Lake
House
Sanibel, FL, 33957, United States
0.9k from Bailey's Beach center

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

3 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$243
Average price / night
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Coastal Cottage on Canal, East End with Pool
Coastal Cottage on Canal, East End with Pool
House
Sanibel, FL, 33957, United States
0.9k from Bailey's Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$305
Average price / night
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Island Sanctuary: Canal Home with Pool, Pets OK!
Island Sanctuary: Canal Home with Pool, Pets OK!
House
Sanibel, FL, 33957, United States
0.9k from Bailey's Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$300
Average price / night
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Modern Canal-Front Gem w/ Lanai + Dock in Sanibel
Modern Canal-Front Gem w/ Lanai + Dock in Sanibel
House
Sanibel, FL, 33957, United States
0.9k from Bailey's Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Microwave, No Smoking, Outdoor Space

3 Bedrooms10 Guests
New to Booking
$393
Average price / night
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 \"Sanibel Oasis\", Private Home with heated pool on a canal
\"Sanibel Oasis\", Private Home with heated pool on a canal
House
Sanibel, FL, 33957, United States
0.9k from Bailey's Beach center

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

3 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$454
Average price / night
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Sandcastle Home on Sanibel Island in The Dunes Golf Club
Sandcastle Home on Sanibel Island in The Dunes Golf Club
House
Sanibel, FL, 33957, United States
0.9k from Bailey's Beach center

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

4 Bedrooms8 Guests
9.4

Superb

3 reviews

$610
Average price / night
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Sanibel Vibes - Relax, Unwind, and Enjoy!
Sanibel Vibes - Relax, Unwind, and Enjoy!
House
Sanibel, FL, 33957, United States
0.9k from Bailey's Beach center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry

5 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$676
Average price / night
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Waterfront 3Bedroom, 2 Bath House in Sanibel Marina
Waterfront 3Bedroom, 2 Bath House in Sanibel Marina
House
Sanibel, FL, 33957, United States
1.0k from Bailey's Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$469
Average price / night
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Stunning Golf Course Villa with Pool
Stunning Golf Course Villa with Pool
House
Sanibel, FL, 33957, United States
1.0k from Bailey's Beach center

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

3 Bedrooms6 Guests
New to Booking
$647
Average price / night
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Canal front beauty!  NEW
Canal front beauty! NEW
House
Sanibel, FL, 33957, United States
1.0k from Bailey's Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

3 Bedrooms6 Guests
New to Booking
$350
Average price / night
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Canal front ground level beauty steps to the beach
Canal front ground level beauty steps to the beach
House
Sanibel, FL, 33957, United States
1.0k from Bailey's Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, No Smoking

3 Bedrooms6 Guests
New to Booking
$411
Average price / night
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SANIBEL SUN CASTLE  Spacious home, heated pool, great location, bike to beach
SANIBEL SUN CASTLE Spacious home, heated pool, great location, bike to beach
House
Sanibel, FL, 33957, United States
1.0k from Bailey's Beach center

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

3 Bedrooms8 Guests
9.8

Exceptional

105 reviews

$684
Average price / night
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Now Available! Enjoy Panoramic Water Views, Pool, Dock, Beach Parking Permit & Pup Friendly!
Now Available! Enjoy Panoramic Water Views, Pool, Dock, Beach Parking Permit & Pup Friendly!
House
Sanibel, FL, 33957, United States
1.0k from Bailey's Beach center

AC, Barbecue, Dryer, Elevator, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$466
Average price / night
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Coastal Charm: Pool Home on Canal on East End!
Coastal Charm: Pool Home on Canal on East End!
House
Sanibel, FL, 33957, United States
1.1k from Bailey's Beach center

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

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$272
Average price / night
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Lovely pool home with golf course views in The Dunes community
Lovely pool home with golf course views in The Dunes community
House
Sanibel, FL, 33957, United States
1.1k from Bailey's Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area

3 Bedrooms6 Guests
New to Booking
$221
Average price / night
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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 Bailey's Beach.

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Bailey's Beach Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 546 verified vacation rentals with a private pool in Bailey's Beach. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Bailey's Beach vary depending on the property size, location, and travel season. Rates typically start from around $164 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 Bailey's Beach also welcome pets. Currently, 29 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 Bailey's Beach often include additional features such as Pool, Private Pool, and Laundry. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Bailey's Beach 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.