Pine Island Vacation Rentals

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Vacation Rentals in Pine Island

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4.0 star property
Bonita Springs
9.2 out of 10, Wonderful, (717)
"great staff, nice rooms, quiet and pleasant get away"
United States
Andy
$184 nightly
The price is $206
Dec 17 - Dec 18
Total with taxes and fees
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Sundial Beach Resort & Spa

5.0 star property
Mid Island
8.6 out of 10, Excellent, (2583)
"wonderful family friendly and spotless resort"
United States
Mary Anne
$363 nightly
The price is $405
Dec 4 - Dec 5
Total with taxes and fees
Sundial Beach Resort & Spa

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1036)
"Clean room, beautiful area, excellent staff"
United States
Crystal
$192 nightly
The price is $215
Dec 14 - Dec 15
Total with taxes and fees
The Suites at Fishermen’s Village- 2 Bedroom Suites

Edison Beach House

3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1569)
"Great room and view! Very clean and comfortable. Would recommend, a great location!"
United States
Catherine
$150 nightly
The price is $167
Dec 4 - Dec 5
Total with taxes and fees
Edison Beach House

GullWing Beach Resort

3.5 star property
South Island
9.4 out of 10, Exceptional, (932)
"The view of the beach was spectacular. "
United States
Carol
$521 nightly
The price is $573
Dec 12 - Dec 13
Total with taxes and fees
GullWing Beach Resort

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

North Captiva
9.6 out of 10, Exceptional, (101)
"Absolutely breathtaking! I couldn’t get enough of the views. Sunrises were beautiful and to watch the storms rolling across the water was definitely a sight to see! The house had everything you needed and was super relaxing! We will definitely be back! The host was also super responsive which makes this home even better! Thank you for a wonderful week! "
United States
Kathleen S.
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

Lazy Cuckoo Inn

2.0 star property
Fort Myers Beach
9.0 out of 10, Wonderful, (222)
"Great location and very clean, cute place"
United States
Sarah
$81 nightly
The price is $91
Dec 18 - Dec 19
Total with taxes and fees
Lazy Cuckoo Inn

Island Inn

3.5 star property
West End
9.4 out of 10, Exceptional, (1120)
"Really nice, updated, and clean room with a screened waterfront balcony in a perfect place on the island (far enough away from the big resorts to be in a quieter area, but close enough to the center area of the island to be convenient). "
United States
Chris
$229 nightly
The price is $255
Dec 14 - Dec 15
Total with taxes and fees
Island Inn

Lovers Key Resort

3.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (1014)
"Nice place"
United States
patrick
$268 nightly
The price is $299
Dec 4 - Dec 5
Total with taxes and fees
Lovers Key Resort

Resort Harbour Properties

3.5 star property
Punta Rassa
9.6 out of 10, Exceptional, (361)
"10/10 would stay there again"
United States
Kristie
$572 nightly
The price is $638
Dec 18 - Dec 19
Total with taxes and fees
Resort Harbour Properties

Sanibel Siesta on the Beach

2.5 star property
Mid Island
10.0 out of 10, Exceptional, (2)
"Near the beach beautiful views and very quiet"
Mexico
Alberto
Sanibel Siesta on the Beach

2 Private Cabanas with kitchen and a Private Pool.

Pelican
9.4 out of 10, Exceptional, (26)
"Property manager was great. Really enjoyed our stay. Would highly recommend others to stay here. "
United States
David H.
2 Private Cabanas with kitchen and a Private Pool.

Seaside 303

3.5 star property
Mid Island
10.0 out of 10, Exceptional, (1)
"The property is all new inside and right on the beach. Gorgeous views, amazing wildlife, beautiful sunsets. We loved it."
United States
Kara
Seaside 303

Luxury family friendly WATERFRONT home with a POOL, PLAYGROUND, FIREPIT & BEACH

Fort Myers
9.6 out of 10, Exceptional, (24)
"Nice place, full of surprises and the back area was nice to use."
United States
Ivan S.
$351 nightly
The price is $387
Dec 4 - Dec 5
Total with taxes and fees
Luxury family friendly WATERFRONT home with a POOL, PLAYGROUND, FIREPIT & BEACH

Matlacha Tiny Village

3.0 star property
Matlacha
8.8 out of 10, Excellent, (267)
"Very nice place with all necesary accommodations for a Pleasant stay. "
United States
isabel
$208 nightly
The price is $223
Dec 14 - Dec 15
Total with taxes and fees
Matlacha Tiny Village

Flamingo Inn

3.0 star property
Mid Island
7.8 out of 10, Good, (983)
"Will definitely stay here again!"
United States
Sasha
$181 nightly
The price is $201
Dec 6 - Dec 7
Total with taxes and fees
Flamingo Inn

BEAUTIFUL NEW CONDO 2025 SANIBEL ISLAND!!! SANDY BEACH POOL 🏝️🌅 🏖️

4.0 star property
Mid Island
9.8 out of 10, Exceptional, (52)
"The condo is beautifully updated and decorated. It was in a great location with an easy and short walk to the beach and a quick drive into an area with shops and restaurants. The owner was always available to assist and had items delivered via Amazon when I inquired about them. The owner provided beach chairs, an umbrella, and beach towels which were nice to have ready to go to enjoy the beach. We had a lovely stay in this Condo. "
United States
Jana J.
BEAUTIFUL NEW CONDO 2025 SANIBEL ISLAND!!! SANDY BEACH POOL 🏝️🌅 🏖️

Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

North Captiva
9.2 out of 10, Wonderful, (19)
"Everything was awesome "
United States
Marlen M.
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

NEW EVERYTHING!! 4-bed 3 bath South Facing spill over spa pool. 2 king suites

3.0 star property
Pelican
10.0 out of 10, Exceptional, (24)
"Great place for a family or friends trip. We really enjoyed having two king suites, a queen bedroom, and an additional smaller bedroom good for kids/teens. The pool and spa were great and everything was just as described. "
United States
Alicia M.
NEW EVERYTHING!! 4-bed 3 bath South Facing spill over spa pool. 2 king suites

Luxurious Waterfront Villa with 4 Bedrooms, Private Heated Pool and Hot Tub!

Pelican
9.8 out of 10, Exceptional, (124)
"Great place to spent your holiday. We really enjoyed the house, the pool and the neighborhood. A full recommendation and a five star rating. Thank you Damien"
Germany
Björn H.
Luxurious Waterfront Villa with 4 Bedrooms, Private Heated Pool and Hot Tub!
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

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 $91 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.