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, (299 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
$221 nightly
The price is $238
Nov 20 - Nov 21
Total with taxes and fees
Matlacha Tiny Village
A beach with two lounge chairs under an umbrella, a person playing with a toy, and another person sitting on the sand.

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
$303 nightly
The price is $338
Nov 29 - Nov 30
Total with taxes and fees
Sundial Beach Resort & Spa
A neatly made bed with a blue patterned pillow, a white towel, and a ceiling fan visible through a large window.

4. 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 beach with people and umbrellas, a railing, and the ocean.

5. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,968 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 tropical garden with a thatched-roof structure, outdoor seating, and various plants.

6. 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 modern hotel with a flat roof, multiple windows, and a sign reading "STUDORES".

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, (185 reviews)
"Location was great."
United States
Joseph
$71 nightly
The price is $80
Nov 19 - Nov 20
Total with taxes and fees
StudioRes by Marriott Fort Myers Airport
A wooden boardwalk leading to a beach with blue beach chairs and umbrellas.

8. 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
$535 nightly
The price is $588
Nov 15 - Nov 16
Total with taxes and fees
GullWing Beach Resort
A modern living room with a large flat-screen TV, a black entertainment unit, a floor lamp, and a view of a garden through a sliding glass door.

9. 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 16 - Nov 17
Total with taxes and fees
Lazy Cuckoo Inn
A beach with a thatched-roof structure, palm trees, and a view of the sea.

10. 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 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
$267 nightly
The price is $298
Nov 22 - Nov 23
Total with taxes and fees
Lovers Key Resort
An aerial view of a rooftop pool area with lounge chairs, a swimming pool, and a staircase leading to an upper deck.

12. Harbour House at the Inn 308

Harbour House at the Inn 308
3.0 star property
Fort Myers Beach
$465 nightly
The price is $518
Nov 14 - Nov 15
Total with taxes and fees
Harbour House at the Inn 308
A covered outdoor area with a pool, seating, and a red umbrella.

13. 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 16 - Nov 17
Total with taxes and fees
Private Pool! Game Room! Very Close to Downtown!
A white door with a window and a circular sign with 'THE DEX' text.

14. The Dex

The Dex
3.0 star property
Mid Island
10.0 out of 10, Exceptional, (1 review)
"Me encanto el apt y todas sus instalaciones. Un excelebte lugar para pasar unos dias en la playa. Si te gusta la vida de playa, este es el lugar."
United States
Pablo
The Dex
A sectional sofa with a chaise, a small table, and a wicker ottoman in an outdoor setting with a clear sky and palm trees.

15. 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 stainless steel appliances, a granite countertop, and a hexagonal tile backsplash.

16. Lakeside Oasis

Lakeside Oasis
2.0 star property
Iona
$225 nightly
The price is $251
Nov 15 - Nov 16
Total with taxes and fees
Lakeside Oasis
A beach with sand, palm trees, and a clear sky.

17. 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
$361 nightly
The price is $403
Nov 14 - Nov 15
Total with taxes and fees
The Wren
A modern apartment with a dining area, kitchen, and living space.

18. Experience Elevated Living in Fort Myers

Experience Elevated Living in Fort Myers
3.0 star property
Fort Myers
Experience Elevated Living in Fort Myers
An aerial view of a swimming pool surrounded by a grassy area with trees and a concrete deck.

19. The Meridian 2825

The Meridian 2825
2.5 star property
Fort Myers
The Meridian 2825
A modern kitchen with a large island, built-in appliances, and a view of a pool.

20. 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
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

Sanibel Island Beach Resort

Sanibel Island Beach Resort

10/10 Excellent
"Room was clean and our towels and coffee we replenished every day. Pool beautiful. Beach chairs always available."
Mary 3-night trip
Posted 6 hours ago
Sanibel Island 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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