B&B in Estero Island
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A coastal cityscape with a marina, dense housing, and a beach.

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your current months are November, 2026 and December, 2026.

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Our top choices for Estero Island bed & breakfast

A modern kitchen with stainless steel appliances, white cabinetry, and a window with blinds.

A bedroom with a bed, a dresser, a TV, a ceiling fan, and a view of an outdoor swimming pool.

A covered swimming pool with lounge chairs, a bar area, and a 'POOL RULES' sign.

A living room with a basketball hoop, a TV, a sofa, and a coffee table.

1. Coastal Naples Escape Private Pool, Sleeps 12, Vanderbilt Beach 5 mins away

Coastal Naples Escape Private Pool, Sleeps 12, Vanderbilt Beach 5 mins away

Naples Park

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"This house is beautiful and has that home feeling. Has everything you might need. The pool was great Best part it's 3 mins away from the beach. Tyson the owner was very helpful. I would definitely recommend 10/10"

Val G.

The price is €381

€381

includes taxes & fees

9 Nov - 10 Nov

Coastal Naples Escape Private Pool, Sleeps 12, Vanderbilt Beach 5 mins away

A hot tub with wooden steps and bar stools, surrounded by potted plants and a grassy area.

A modern kitchen with a dining area, featuring a coffee and tea bar, a unique ceiling light, and a clock on the wall.

A modern living room with a sofa, ottoman, and a dining area with a table and chairs.

A modern kitchen with blue cabinets, stainless steel appliances, and a marble countertop.

2. TR's Bed & Breakfast

TR's Bed & Breakfast

Pelican

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"If you are looking for a home away from home, this B&B will be it! R&T are great host's and have created a need place with spacious, modern rooms. You will find the open dinning area to sit and socialize (if you are inclined to hang out with fellow travelers) or just enjoy it for breakfast. The yard is as shown in the pictures and a nice place to hang out in the evening. "

Frank B.

The price is €211

€211

includes taxes & fees

9 Nov - 10 Nov

TR's Bed & Breakfast

A waterfront property with colorful houses, a dock, and a sandy beach.

A beachside area with colorful beach houses, a sandy beach, and palm trees.

A narrow hallway with a green wall, wicker chairs, a black sofa, and a colorful rug.

A kitchen with white cabinets, a granite countertop, a sink, a coffee maker, and a refrigerator. There is a window with blinds and a green door with a sign.

3. Matlacha Tiny Village- Iguana

Matlacha Tiny Village- Iguana

Matlacha

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"This was a charming place to stay, very quiet & exactly what we neded to refresh & recharge. Would highly recommend!"

Carly D.

The price is €235

€235

includes taxes & fees

9 Nov - 10 Nov

Matlacha Tiny Village- Iguana

A wooden deck with picnic tables and chairs, a shaded area, and a view of a marina with boats and buildings.

A compact kitchen with a built-in stove, a coffee maker, and a refrigerator.

4. Matlacha Tiny Village - Flamingo

Matlacha Tiny Village - Flamingo

Matlacha

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Thoughtful owners. Great communication from booking to checkout."

Anonymous traveller

The price is €242

€242

includes taxes & fees

12 Nov - 13 Nov

Matlacha Tiny Village - Flamingo

A narrow kitchen with a built-in seating area, a refrigerator, and a ceiling fan.

5. Matlacha Tiny Village - Dolphin

Matlacha Tiny Village - Dolphin

Matlacha

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Fabulous! Perfect for a quick family getaway. Many shops within walking distance"

Mary M.

The price is €242

€242

includes taxes & fees

9 Nov - 10 Nov

Matlacha Tiny Village - Dolphin

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Learn more about Estero Island

Venture to sights like Castle Beach and Estero Boulevard Beach as you discover Estero Island.

See all hotels in Estero Island

Top reviews in Estero Island

A high-rise hotel with multiple floors, a rooftop pool, and a marina in the background.

A beach with a clear sky, palm trees, and a sunlit ocean.

A bedroom with a bed, a ceiling fan, a dresser, a television, and a large window with a view of the ocean.

A hotel pool area with lounge chairs and a water feature.

GullWing Beach Resort

South Island

10/10 Excellent

Second time to stay in Gullwing and hopefully will return in the future. Amazing property, largest most spacious Condos you will experience for great price. White sandy Beach is just so relaxing and a little piece of paradise , Beach feels very much your own as never busy unlike Time Square end of Fort Myers Beach. "SUNSETS" Amazing, Just perfect !!!!!!!

Hylo

Reviewed November 6, 2013Reviewed November 6, 2013

GullWing Beach Resort

A sectional sofa with a chaise, a small table, and a wicker ottoman in an outdoor setting with a clear sky and palm trees.

A bedroom with a bed, bedside table, lamp, and a painting on the wall.

A modern living room with a grey armchair, a glass coffee table, and a dining area with a chandelier.

A kitchen with white cabinets, a stainless steel refrigerator, and a chandelier.

Flamingo Inn

Mid Island

8/10 Good

Beautiful getaway during the long cold winter up north

Robert

Reviewed January 28, 2015Reviewed January 28, 2015

Flamingo Inn

A spacious lobby with a grand piano, a reception desk, and a chandelier.

A spacious lobby with a grand piano, comfortable seating, and a polished floor.

A hotel lobby with multiple seating areas, a bar, and large windows offering views of the outdoors.

A balcony with a table and chairs, a vase with red flowers, and a view of a body of water and buildings in the distance.

Inn at Pelican Bay

Pelican Bay

10/10 Excellent

It was amazing Staff were so friendly and accommodating Can’t wait to go back

Moakes

Reviewed November 28, 2019Reviewed November 28, 2019

Inn at Pelican Bay

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Search Bed and Breakfast in Estero Island

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Estero Island bed & breakfast

1. Coastal Naples Escape Private Pool, Sleeps 12, Vanderbilt Beach 5 mins away

2. TR's Bed & Breakfast

3. Matlacha Tiny Village- Iguana

4. Matlacha Tiny Village - Flamingo

5. Matlacha Tiny Village - Dolphin

Learn more about Estero Island

Top reviews in Estero Island

GullWing Beach Resort

10/10 Excellent

Explore a world of travel with Expedia