A wooden pier extending into calm water with a clear sky and distant land.

Search Pine Island Cottage Rentals

Where to?

Dates

November 2026

December 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Find vacation rentals that suit your style

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Pine Island cottages

A hot tub with water bubbling, a life ring on the door, and a sign prohibiting chemicals.

1. Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida

Bokeelia

Lisa E.

￥33,657 total

includes taxes & fees

Nov 9 - Nov 10

A small, single-story building with a white exterior and a green roof, labeled 'Malu Lento.'

2. Malu Lani Cottage at Pirates Cove Inn & Marina - Boat Slip Included

Bokeelia

￥62,516 total

includes taxes & fees

Nov 16 - Nov 17

A two-story house with a brick driveway leading to a front door, surrounded by various plants and trees.

3. The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse

East End

Trina S.

￥53,887 total

includes taxes & fees

Nov 7 - Nov 8

A covered patio with a table and chairs, a thatched roof, and a view of a blue house and greenery.

4. Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS

West End

Robin H.

￥67,074 total

includes taxes & fees

Nov 30 - Dec 1

A single-story building with a beige exterior and a red door.

5. Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

East End

Stephen

￥46,446 total

includes taxes & fees

Nov 20 - Nov 21

A bathroom with a toilet, sink, and mirror.

6. Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!

East End

Eric W.

￥46,603 total

includes taxes & fees

Nov 9 - Nov 10

A house with a gravel driveway leading to a blue building with a porch.

7. Beach Days & Backyard Nights! Fort Myers Retreat

Harlem Heights

￥52,890 total

includes taxes & fees

Nov 25 - Nov 26

A wooden deck with benches, surrounded by palm trees and a body of water, with a caution sign visible.

8. Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes

West End

Catherine B.

￥62,149 total

includes taxes & fees

Nov 20 - Nov 21

A room with a large white door leading to an outdoor area with a wicker chair and a bottle of wine.

9. Historic PO Cottage Garden Suite Steps to Beach - Casual Lux Décor - Jensen's "On the Gulf" 6

Captiva

Juan

￥100,672 total

includes taxes & fees

Nov 7 - Nov 8

A covered patio area with a table and chairs, large windows, and a view of the surrounding landscape.

10. Gorgeous Newly Renovated Coastal Cottage "Egret" Minutes to the beach and free bikes!! JULY SAVINGS!

West End

Nancy K.

￥63,315 total

includes taxes & fees

Nov 12 - Nov 13

A two-story house with a covered porch, a small front yard, and a palm tree.

11. Romantic Getaway, #302, 2 min walk to the beach.

Mid Island

Joseph W.

￥57,224 total

includes taxes & fees

Nov 8 - Nov 9

A small, wooden building with a sign for guest laundry and a cart labeled "The Parrot Nest."

12. Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!

East End

Laurén A.

￥46,446 total

includes taxes & fees

Nov 15 - Nov 16

A garage with a metal gate and a driveway leading to a house.

13. Cozy cottage at Sunseekers Resort. Pool, pets,pickleball,close to everything!

Jacarandas

Kari M.

￥31,743 total

includes taxes & fees

Nov 8 - Nov 9

A small building with a sign for guest laundry and beach carts.

14. The Rosella-Great value on Sanibel! Walk to dining, shops and The Lighthouse-on Historic East End!

East End

Dan S.

￥45,658 total

includes taxes & fees

Nov 17 - Nov 18

A row of three beach houses with white railings and a gravel driveway.

15. Iconic Anchor Inn A-Frame Cottages

Mid Island

Teresa H.

￥41,507 total

includes taxes & fees

Nov 8 - Nov 9

16. Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!

East End

Anonymous traveler

￥45,658 total

includes taxes & fees

Nov 9 - Nov 10

A covered patio with a pool table, chairs, and a dining table.

17. 3 Mi to Fort Myers Beach! Family Getaway w/ Pool

Iona

￥69,302 total

includes taxes & fees

Dec 1 - Dec 2

A modern building with a glass facade, surrounded by tropical vegetation and outdoor seating.

18. Historic Captiva PO Cottage Garden Suite Steps to Beach Casual Lux Décor - Jensen's "On the Gulf" 7

Captiva

Anonymous traveler

￥86,478 total

includes taxes & fees

Nov 10 - Nov 11

A wooden deck with chairs and tables overlooking a body of water, surrounded by trees and greenery.

19. Peaceful Cute Cottage 1.5Mi to Beach Shared Dock on Imperial River Launch MAN

Bonita Shores

Rykadin

￥28,933 total

includes taxes & fees

Nov 7 - Nov 8

20. Spacious Cottage Close To Beach 1.5 Mi On Park Like Gulf Access River W Dock ST

Bonita Shores

Ty B.

￥33,292 total

includes taxes & fees

Nov 7 - Nov 8

View all properties

Learn more about Pine Island

Head to sights like Phillips Community Park and Museum of the Islands as you discover Pine Island.

See all hotels in Pine Island

Top reviews in Pine Island

A waterfront patio with Adirondack chairs, a fire pit, and a view of the water.

Matlacha on Shoreview

Cape Coral

10/10 Excellent

Upon arrival room was ready. We received the room we booked, lower level, one bedroom suite poolside with screen porch. It was clean, cool, and ready for occupants. The area was very safe and the property was very well maintained and quiet. We liked fishing from the dock and caught quite a variety of fish. We would definitely stay there again. In addition they had very good internet and a nice large TV which my husband was able to enjoy football.

Pamela

A Holiday Inn Express building with a clear entrance, palm trees, and a purple sky.

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Caloosahatchee

10/10 Excellent

Lina

A multi-story hotel with a modern facade, a covered entrance, and a landscaped front area.

Fairfield Inn & Suites by Marriott Cape Coral/North Fort Myers

Hancock

10/10 Excellent

Raydel

A resort with a pool, thatched umbrellas, and palm trees.

Off the Charts Inn & Out Island Resort

Saint James City

10/10 Excellent

The property was in the middle of a remodel so there were only 5 rooms available which made it very quiet. The unit was very clean. The amazing thing about the property was the canal in the back. The manatees were swimming around everyday. They were awesome to see. One evening there were dolphins playing in the canal. There was a great restaurant within walking distance that had great food, drinks and live music every night.

Bobbie

A two-story building with a blue exterior, a dock, and a boat.

MALU LANI Inn & Marina

Bokeelia

10/10 Excellent

Kyle

An outdoor dining area with tables and chairs, a fire pit, and a view of the water.

The Westin Cape Coral Resort At Marina Village

Pelican

10/10 Excellent

danica

A Hampton Inn & Suites hotel entrance with a 'Welcome' sign, palm trees, and a well-lit facade.

Hampton Inn & Suites - Cape Coral/Fort Myers Area, FL

Caloosahatchee

10/10 Excellent

Jack

A Hampton Inn hotel with a well-lit entrance, a covered outdoor area, and a parking lot.

Hampton Inn Fort Myers Downtown

Fort Myers River District

10/10 Excellent

The property was very updated and clean. It had a warm breakfast breakfast buffet every morning eggs, bacon, waffles, bagels, toast, fruit, yogurt and juices. Enough to get you by until lunch. Staff was very friendly and helpful with any questions that I had. The only negative thing that I have to say is that I was there for four nights and housekeeping only came in once. However, I highly recommend this hotel.

Rhonda

A resort with multiple-story buildings, palm trees, and a well-maintained lawn.

Sanibel Island Beach Resort

Mid Island

10/10 Excellent

Linda

A hotel with multiple buildings, a pool area, and a beach.

Pink Shell Beach Resort and Marina

Fort Myers Beach

10/10 Excellent

This is a wonderful place, the adult pool was priceless because of so many children. Food was exceptional for a resort, the only real gripe is the drink prices. 9 bucks for a draft Modelo in a plastic cup. I had two mixed drinks and the wife two Mocktails and it was $60 dollars. I get it, its a resort but they are making a killing off the booze, I noticed many folks just brought their own because of this. Lower the price and you will sell more.

TIMOTHY KEVIN

An outdoor patio with tables and chairs, umbrellas, and a pool in the background.

Holiday Inn Express & Suites Ft Myers Beach-Sanibel Gateway by IHG

Fort Myers Beach

10/10 Excellent

I would stay here again in a minute! Conveniently located just off Fort Myers Beach, next to Walmart, bus station, and main highway. Staff was exceptional with kindness and immediate response to requests. Hotel is clean clean clean! Breakfast was yummy and had different choices daily. I’m a late breakfast eater so having a refrigerator and microwave in my room was convenient for heating breakfast up later in morning after grabbing it early. Book here..you won’t be sorry!

Dennette

A balcony with a view of the beach, wicker chairs, a table, and a railing.

Margaritaville Beach Resort Fort Myers

Fort Myers Beach

10/10 Excellent

Angela

A modern hotel with a central entrance, multiple floors, and a landscaped area with palm trees.

Hampton Inn & Suites Fort Myers - Colonial Blvd

Fort Myers

10/10 Excellent

We ended up checking in to a close by hotel that we had made reservations for and checking right out because it was absolutely disgusting. We went over to Hampton Inn and luckily, Crystal was able to help us book the last available room in the hotel. I have to say, we had an amazing stay here. The staff was truly so nice, respectful and accommodating. The rooms and the hotel were super clean. They served breakfast every morning in the lobby and it was pretty good!! The pool was absolutely...

Anonymous traveler

A balcony with white chairs and a table overlooking a beach with palm trees and a tennis court.

Best Western Plus Beach Resort

Fort Myers Beach

10/10 Excellent

newly re-opened, clean, staff was fantastic, pleasant, social, housekeepers were excellent, (thank God for English to Spanish app). clean up from hurricane still going on so beach a little noisy but still relaxing. didn't like that there wasn't a safe in room, beds and linens very comfortable, breakfast was fresh/hot/good selection, great coffee. good company with a parrot named Coco lol. would stay again and recommend

paula

A swimming pool area with lounge chairs and palm trees, surrounded by buildings and a sunset view.

Sanibel Inn

East End

10/10 Excellent

Kurt

A Holiday Inn Express building with a modern design, featuring a flat facade and a covered entrance area.

Holiday Inn Express & Suites Fort Myers Airport by IHG

Daniels Corridor

10/10 Excellent

A Drury Inn & Suites hotel with a parking lot full of cars.

Drury Inn & Suites Fort Myers Airport FGCU

Miromar Lakes

10/10 Excellent

Sharmaine

A modern hotel with a covered entrance, multiple floors, and a landscaped area with plants and outdoor seating.

Home2 Suites by Hilton Fort Myers Colonial Blvd

Fort Myers

10/10 Excellent

Anonymous traveler

Frequently Asked Questions

How much do cottages in Pine Island cost?

Prices for cottages in Pine Island range between ￥12,442 and ￥47,247 per night. No matter your budget, you'll find a perfect place to immerse yourself in nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many cottages are there in Pine Island?

Take your pick of cottages in Pine Island. Whether you're traveling with the kids, as a table-for-two or with a group of close friends, Expedia can help you find the ideal space.

What are the best cheap cottages in Pine Island?

Save cash on your Pine Island escape by selecting cottages from just ￥12,442 per night. Preparing to explore the must-visit attractions of Saint James City? Put your luggage down at 810 Third Street - 2 Bedroom Cottage, a budget-friendly option with a barbecue grill and WiFi. If you're basing yourself in Bokeelia, Boca Grande Shores 06 - 3bedroom Home is a terrific choice. It features a swimming pool and a porch and provides a superb opportunity to experience life in the slow lane for a while. There are lots of free and interesting attractions wherever you're visiting in Pine Island. If you're staying in Saint James City, be sure to visit Sanibel Island Southern Beach. You can also go sightseeing on a shoestring in Bokeelia. North Captiva Island Beach is a top free attraction here. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Are there any family-friendly cottages in Pine Island?

You can find family-friendly cottages in destinations around Pine Island, including Saint James City. Seahorse Cottages On Sanibel is one option that will cater to your needs in this renowned city. It has a 3-star rating and useful amenities like beach umbrellas and a picnic area. Also consider Cozy Cottage / Great Location. With clothes washing facilities and an oven, this 3-star cottage in Saint James City will make your family feel welcome. Saint James City offers lots of family-friendly attractions when it's time to tour the sights. Sanibel Island Southern Beach and Captiva Beach has something for all ages.

Why book your cottage in Pine Island with Expedia?

Expedia has some superb cottages in Pine Island, so start packing for an unforgettable vacay on nature's doorstep. If you have a certain budget, choose how much you want to spend and the star rating of your property. Or, try out our filters to search for cottages with a hot tub or a kitchen. We'll help you find the perfect digs whatever your trip looks like.

How can I find cheap cottages in Pine Island?

The simplest way to find cheap cottages in Pine Island is with Expedia's useful filter tool. Narrow down your search results by amenities, budget and star rating to land unbeatable bargains in a few clicks.

Explore a world of travel with Expedia

Car rentals near Hertz Arena
Standard Link for Car rentals near Hertz Arena

Search Pine Island Cottage Rentals

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Pine Island cottages

1. Captain's Cottage: One-bedroom cottage with a spa in tropical Bokeelia, Florida

2. Malu Lani Cottage at Pirates Cove Inn & Marina - Boat Slip Included

3. The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse

4. Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS

5. Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

6. Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!

7. Beach Days & Backyard Nights! Fort Myers Retreat

8. Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes

9. Historic PO Cottage Garden Suite Steps to Beach - Casual Lux Décor - Jensen's "On the Gulf" 6

10. Gorgeous Newly Renovated Coastal Cottage "Egret" Minutes to the beach and free bikes!! JULY SAVINGS!

11. Romantic Getaway, #302, 2 min walk to the beach.

12. Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!

13. Cozy cottage at Sunseekers Resort. Pool, pets,pickleball,close to everything!

14. The Rosella-Great value on Sanibel! Walk to dining, shops and The Lighthouse-on Historic East End!

15. Iconic Anchor Inn A-Frame Cottages

16. Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!

17. 3 Mi to Fort Myers Beach! Family Getaway w/ Pool

18. Historic Captiva PO Cottage Garden Suite Steps to Beach Casual Lux Décor - Jensen's "On the Gulf" 7

19. Peaceful Cute Cottage 1.5Mi to Beach Shared Dock on Imperial River Launch MAN

20. Spacious Cottage Close To Beach 1.5 Mi On Park Like Gulf Access River W Dock ST

Learn more about Pine Island

Top reviews in Pine Island

Matlacha on Shoreview

10/10 Excellent

Frequently Asked Questions

How much do cottages in Pine Island cost?

How many cottages are there in Pine Island?

What are the best cheap cottages in Pine Island?

Are there any family-friendly cottages in Pine Island?

Why book your cottage in Pine Island with Expedia?

How can I find cheap cottages in Pine Island?

Explore a world of travel with Expedia