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

Pine Island Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Pine Island vacation rentals

A beach with a prominent dead tree trunk, sandy shore, and calm sea.

1. MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property, peaceful, clean rental. Super responsive owner and all the things you need. Perfect location for boaters. Loved this stay and would definitely rent again! "
United States
April
$358 nightly
The price is $390
Nov 16 - Nov 17
Total with taxes and fees
MALU LANI Inn & Marina
A beachside area with colorful beach houses, a dock, and a sandy beach.

2. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (300 reviews)
"Such a cute place that we have never heard of! Walked to cute tiny shops, got awesome bbq……… very quaint and quiet. Had a great time."
United States
Shannon
$206 nightly
The price is $221
Nov 21 - Nov 22
Total with taxes and fees
Matlacha Tiny Village
A pool area with lounge chairs and umbrellas, a beach with umbrellas and lounge chairs, and palm trees.

3. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,720 reviews)
"Great trip, beautiful island and great location!"
United States
Jeremy
$289 nightly
The price is $322
Dec 15 - Dec 16
Total with taxes and fees
Sundial Beach Resort & Spa
A balcony with a TV, a chair, and a view of a beach with a pier.

4. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,972 reviews)
"Best place ever"
United States
Joshua
$221 nightly
The price is $247
Nov 17 - Nov 18
Total with taxes and fees
Edison Beach House
A beach with a view of the ocean and a sunset.

5. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,169 reviews)
"Upon arrival, the front desk was very helpful explaining everything in detail. The room was very clean & spacious and had everything we needed for our stay. The location on the beach and the view was AMAZING!! We would definitely stay here again…HIGHLY RECOMMEND!!!"
United States
Elizbeth
$219 nightly
The price is $244
Nov 19 - Nov 20
Total with taxes and fees
Island Inn
A modern living room with a flat-screen TV, a floor lamp, a dining table, and a sofa.

6. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (311 reviews)
"Great location. Great night sleep"
United States
Stephanie
$83 nightly
The price is $92
Nov 23 - Nov 24
Total with taxes and fees
Lazy Cuckoo Inn
A modern hotel room with a kitchenette, a bed, a seating area, and a wardrobe.

7. StudioRes by Marriott Fort Myers Airport

StudioRes by Marriott Fort Myers Airport
3.0 star property
Fort Myers
9.2 out of 10, Wonderful, (186 reviews)
"Location was great."
United States
Joseph
$71 nightly
The price is $80
Nov 22 - Nov 23
Total with taxes and fees
StudioRes by Marriott Fort Myers Airport
A beach with a thatched-roof structure, palm trees, and a view of the sea.

8. The Suites at Fishermen’s Village

The Suites at Fishermen’s Village
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,371 reviews)
"Great place to stay but comes with a price."
United States
John
$192 nightly
The price is $215
Nov 30 - Dec 1
Total with taxes and fees
The Suites at Fishermen’s Village
A spacious living room with a grey sofa, striped armchair, and a woven coffee table. Large windows offer a view of a tropical garden.

9. Driftwood Inn

Driftwood Inn
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (11 reviews)
"Great place to stay on sanibel"
United States
Terri
$426 nightly
The price is $475
Nov 15 - Nov 16
Total with taxes and fees
Driftwood Inn
A marina with boats docked, a bridge overhead, and buildings with outdoor seating.

10. Harbour House at the Inn 308

Harbour House at the Inn 308
3.0 star property
Fort Myers Beach
$455 nightly
The price is $507
Nov 15 - Nov 16
Total with taxes and fees
Harbour House at the Inn 308
A balcony with wicker furniture, a bottle, and glasses, overlooking a sunset over a body of water and buildings.

11. Lovers Key Resort

Lovers Key Resort
3.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (1,097 reviews)
"Room location had a amazing view"
United States
Joanne
$273 nightly
The price is $304
Nov 15 - Nov 16
Total with taxes and fees
Lovers Key Resort
A resort with multiple buildings, a swimming pool, and a beach.

12. Sanibel Beach Club

Sanibel Beach Club
3.5 star property
Mid Island
10.0 out of 10, Exceptional, (2 reviews)
"I recently traveled with my family to this apartment, and we were thoroughly impressed. The apartment smelled clean and fresh, and the beds and pillows were incredibly comfortable. I highly recommend this property to families. The spa and pool were great, and the balcony offered a stunning view of the ocean. I even called the emergency number around 11pm for a problem with the air conditioning, and Sal, the maintenance guy, promptly fixed it. The condo is very quiet and well-maintained."
United States
Yusniel
$244 nightly
The price is $272
Dec 9 - Dec 10
Total with taxes and fees
Sanibel Beach Club
A beach with a clear sky, palm trees, and a sunlit ocean.

13. GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.6 out of 10, Exceptional, (987 reviews)
"Gullwing is an excellent beach front condo property. Very well maintained, friendly staff and close to amenities."
United States
Jennifer
$532 nightly
The price is $584
Dec 15 - Dec 16
Total with taxes and fees
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.

14. Flamingo Inn

Flamingo Inn
3.0 star property
Mid Island
8.0 out of 10, Very good, (1,028 reviews)
"Cute, clean, beachside inn. Will definitely be back!"
United States
Emily
$153 nightly
The price is $171
Nov 15 - Nov 16
Total with taxes and fees
Flamingo Inn
A modern kitchen with a dining area, featuring a large glass table set for four, a ceiling fan, and a wall clock.

15. Private Pool! Game Room! Very Close to Downtown!

Private Pool! Game Room! Very Close to Downtown!
3.0 star property
Hancock
$487 nightly
The price is $543
Nov 19 - Nov 20
Total with taxes and fees
Private Pool! Game Room! Very Close to Downtown!
A beach with sand, palm trees, and a clear sky.

16. The June

The June
2.0 star property
Mid Island
9.8 out of 10, Exceptional, (8 reviews)
"The stay was great the place was nice, clean, and in a great location!"
United States
Alexzandria
$318 nightly
The price is $355
Nov 25 - Nov 26
Total with taxes and fees
The June
A modern living room with a dining area, a grey sofa, a coffee table, and a wall clock.

17. Lakeside Oasis

Lakeside Oasis
2.0 star property
Iona
$220 nightly
The price is $246
Nov 16 - Nov 17
Total with taxes and fees
Lakeside Oasis
A beach with sand, palm trees, and a clear sky.

18. The Wren

The Wren
3.0 star property
Mid Island
10.0 out of 10, Exceptional, (3 reviews)
"What a place to stay! We had a truly great stay here and it’s a really nice place and so close to the beach! We definitely felt like we got our money worth and would absolutely stay there again. This was perfect for my family vacation. Top ratings for this place."
United States
Michael P
$288 nightly
The price is $321
Nov 15 - Nov 16
Total with taxes and fees
The Wren
A modern kitchen with white cabinetry, a central island, and stainless steel appliances.

19. Riverfront Home w Private Dock Pool Beaches

Riverfront Home w Private Dock Pool Beaches
2.0 star property
McGregor
$834 nightly
The price is $930
Nov 15 - Nov 16
Total with taxes and fees
Riverfront Home w Private Dock Pool Beaches
A resort with a swimming pool, outdoor seating, and a well-lit building.

20. Modern 2BR Fort Myers Condo Pool, BBQ & Near Beaches

Modern 2BR Fort Myers Condo Pool, BBQ & Near Beaches
3.0 star property
Three Oaks
6.0 out of 10, (2 reviews)
"Loved this place! Pool area was very nice too! Will come again!"
United States
Robin L
$280 nightly
The price is $291
Nov 25 - Nov 26
Total with taxes and fees
Modern 2BR Fort Myers Condo Pool, BBQ & Near Beaches
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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Top Pine Island Hotel Reviews

DiamondHead Beach Resort

DiamondHead Beach Resort

8/10 Good
"The suite we were in 910, has a very nice view of the ocean. The suite was very comfortable but the bed was too firm for us. The fans below at sidewalk level are very noisy and can be heard while sitting on the spacious balcony. We also thought Mojos was indoors with seating. It is a food truck outside. We ate at Cabanas which was very good. We will be returning to this resort."
Dolores 2-night trip
Posted 9 hours ago
DiamondHead Beach Resort

Find out more about Pine Island

Everything you need to know about Pine Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pine Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pine Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pine Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pine Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pine Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $80 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pine Island rentals

At Expedia, we put the best Pine Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pine Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pine Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pine Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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