Cottage Rentals in Bailey's Beach, FL: Compare 10+ Sites & Save

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29 Best Cottage Rentals in Bailey's Beach (Starting from $100)

Sanibel-Style on the East End! Walk to restaurants and the lighthouse.  NEW!
Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!
Cottage
Sanibel, FL, 33957, United States
1.2k from Bailey's Beach center

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

1 Bedroom3 Guests
9.6

Exceptional

53 reviews

$380
Average price / night
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Sanibel Shores B1: A delightful cottage in charming Sanibel
Sanibel Shores B1: A delightful cottage in charming Sanibel
Cottage
Sanibel, FL, 33957, United States
1.3k from Bailey's Beach center

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

1 Bedroom4 Guests
New to Booking
$266
Average price / night
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WORK FROM HOME - LIVE IN PARADISE! \nLive on Sanibel Island - Walk to the beach!
WORK FROM HOME - LIVE IN PARADISE! \nLive on Sanibel Island - Walk to the beach!
Cottage
Sanibel, FL, 33957, United States
1.3k from Bailey's Beach center

AC, Dryer, Heater, Laundry, No Smoking, Washer

2 Bedrooms2 Guests
New to Booking
$100
Average price / night
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quite newly refurbished Cottage walking distance to beach small complex
quite newly refurbished Cottage walking distance to beach small complex
Cottage
Sanibel, FL, 33957, United States
1.4k from Bailey's Beach center

AC, Heater, Internet, Laundry, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$294
Average price / night
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Iconic Anchor Inn A-Frame Cottages
Iconic Anchor Inn A-Frame Cottages
Cottage
Sanibel, FL, 33957, United States
1.4k from Bailey's Beach center

No Smoking

3 Bedrooms6 Guests
New to Booking
$381
Average price / night
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Newly remodeled Parrot Nest Toucan Cottage!  Walk to beach, shops, restaurants!
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
Cottage
Sanibel, FL, 33957, United States
1.4k from Bailey's Beach center

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

1 Bedroom2 Guests
9.6

Exceptional

48 reviews

$383
Average price / night
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Newly remodeled Parakeet cottage!  Walking distance to beach, restaurants, shops!
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
Cottage
Sanibel, FL, 33957, United States
1.5k from Bailey's Beach center

AC, Barbecue, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, Patio

1 Bedroom2 Guests
9.2

Superb

72 reviews

$388
Average price / night
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Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
Cottage
Sanibel, FL, 33957, United States
1.6k from Bailey's Beach center

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

1 Bedroom3 Guests
9.4

Superb

61 reviews

$386
Average price / night
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Charming Coastal Retreat at Sanibel Shores-Walk to the Beach PET FRIENDLY
Charming Coastal Retreat at Sanibel Shores-Walk to the Beach PET FRIENDLY
Cottage
Sanibel, FL, 33957, United States
1.7k from Bailey's Beach center

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

2 Bedrooms4 Guests
8.0

Good

2 reviews

$334
Average price / night
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Island Charm Meets Modern Comfort — Walk to Sanibel’s Beautiful Beaches!
Island Charm Meets Modern Comfort — Walk to Sanibel’s Beautiful Beaches!
Cottage
Sanibel, FL, 33957, United States
1.7k from Bailey's Beach center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$326
Average price / night
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2 Bedroom Cottage Sanibel Island Near Beach-Great! Newly renovated & refurnished
2 Bedroom Cottage Sanibel Island Near Beach-Great! Newly renovated & refurnished
Cottage
Sanibel, FL, 33957, United States
1.7k from Bailey's Beach center

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

2 Bedrooms4 Guests
9.6

Exceptional

20 reviews

$291
Average price / night
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Near Beach! 2 Bedroom Cottage Sanibel Island
Near Beach! 2 Bedroom Cottage Sanibel Island
Cottage
Sanibel, FL, 33957, United States
1.7k from Bailey's Beach center

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

2 Bedrooms4 Guests
9.2

Superb

45 reviews

$262
Average price / night
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 Casa Blanca Cottage -  East Lighthouse End
Casa Blanca Cottage - East Lighthouse End
Cottage
Sanibel, FL, 33957, United States
1.7k from Bailey's Beach center

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

3 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$192
Average price / night
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The Rosella-Great value on Sanibel! Walk to dining, shops and The Lighthouse-on Historic East End!
The Rosella-Great value on Sanibel! Walk to dining, shops and The Lighthouse-on Historic East End!
Cottage
Sanibel, FL, 33957, United States
1.7k from Bailey's Beach center

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

1 Bedroom3 Guests
9.2

Superb

39 reviews

$380
Average price / night
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The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse
The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse
Cottage
SANIBEL, FL, 33957, United States
1.8k from Bailey's Beach center

AC, Barbecue, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, Patio

1 Bedroom4 Guests
9.2

Superb

52 reviews

$422
Average price / night
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Romantic Getaway, #302, 2 min walk to the beach.
Romantic Getaway, #302, 2 min walk to the beach.
Cottage
Sanibel, FL, 33957, United States
2.2k from Bailey's Beach center

AC, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio

1 Bedroom3 Guests
9.4

Superb

71 reviews

$549
Average price / night
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Waterside Cottage: Newly Renovated on canal w 26’ boat dock!
Waterside Cottage: Newly Renovated on canal w 26’ boat dock!
Cottage
Saint James City, FL, 33956, United States
6.2k from Bailey's Beach center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$192
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
8.4k from Bailey's Beach 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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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
8.5k from Bailey's Beach 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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Life's a Beach,  A charming Beach Cottage
Life's a Beach, A charming Beach Cottage
Cottage
Fort Myers Beach, FL, 33931, United States
8.5k from Bailey's Beach center

AC, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms5 Guests
9.2

Superb

14 reviews

$248
Average price / night
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Charming Beach Cottage
Charming Beach Cottage
Cottage
Fort Myers Beach, FL, 33931, United States
8.5k from Bailey's Beach center

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

1 Bedroom4 Guests
9.8

Exceptional

8 reviews

$161
Average price / night
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Charming 2-bedroom cottage in lovely Fort Myers Beach located 2 miles from beach
Charming 2-bedroom cottage in lovely Fort Myers Beach located 2 miles from beach
Cottage
Fort Myers Beach, FL, 33931, United States
8.8k from Bailey's Beach center

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

2 Bedrooms6 Guests
New to Booking
$164
Average price / night
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Pink Palm*Steps to Beach*Pool & Sofa Bed- Walk to Times Square, Fort Myers Beach
Pink Palm*Steps to Beach*Pool & Sofa Bed- Walk to Times Square, Fort Myers Beach
Cottage
Fort Myers Beach, FL, 33931, United States
8.9k from Bailey's Beach center

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

1 Bedroom3 Guests
New to Booking
$284
Average price / night
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Cozy cottage near Ft Myers beach, Sanibel Captiva Pet Friendly!!!
Cozy cottage near Ft Myers beach, Sanibel Captiva Pet Friendly!!!
Cottage
Fort Myers, FL, 33908, United States
9.2k from Bailey's Beach center

AC, Arcade, Barbecue, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

1 Bedroom2 Guests
New to Booking
$138
Average price / night
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Private Home - Steps away from beach - Newly Renovated
Private Home - Steps away from beach - Newly Renovated
Cottage
Fort Myers Beach, FL, 33931, United States
9.3k from Bailey's Beach center

AC, Dryer, Hot Tub, Laundry, No Smoking, Pool, Washer

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$496
Average price / night
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DEJA BLUE  1000 FT from Beach  Great for Families
DEJA BLUE 1000 FT from Beach Great for Families
Cottage
Ft myers beach, FL, 33931, United States
9.4k from Bailey's Beach center

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

2 Bedrooms4 Guests
9.8

Exceptional

49 reviews

$293
Average price / night
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Quaint beautiful backyard sanctuary
Quaint beautiful backyard sanctuary
Cottage
Fort Myers Beach, FL, 33931, United States
9.5k from Bailey's Beach center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$807
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 Cottage Rentals in Bailey's Beach.

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Frequently Asked Questions

You can explore 29 verified cottage rentals in Bailey's Beach. Our listings are sourced from a range of trusted booking providers, giving you access to charming coastal cottages, peaceful countryside escapes, and cozy stays—all in one place.

Cottage rental prices in Bailey's Beach vary based on the season, location, and amenities offered. Rates typically start from around $100 per night, with higher prices during peak travel periods or in waterfront locations. Comparing different options can help you find a stay that fits both your preferences and budget.

Many cottages in Bailey's Beach feature inviting outdoor areas such as private gardens, patios, or small yards. These spaces are ideal for relaxing, dining outdoors, or enjoying the surrounding scenery. You can use the available filters to quickly find cottages with outdoor features that match your preferences.

Yes, cottages are often a great choice for travelers with pets thanks to their cozy layouts and access to outdoor space. Currently, 10 listings in Bailey's Beach welcome pets, making it easier to plan a comfortable stay with your companion.

For busy seasons such as summer holidays or long weekends, it’s a good idea to book your cottage 60 to 90 days in advance. Since cottages are typically smaller and more unique, the most desirable options tend to get reserved quickly during peak periods.

Cottages in Bailey's Beach are known for their comfort and charm, often including amenities such as Fireplace/Heating, Bedding/Linens, and Kitchen. These features help create a relaxing and home-like atmosphere for guests.

Yes, many cottages in Bailey's Beach are well-suited for longer stays. They often include essentials like full kitchens, laundry facilities, and comfortable living spaces, making them a practical option for extended vacations or remote work.