Pine Island Vacation Rentals

Vacation Rentals in Pine Island

Fridge, microwave, oven, coffee/tea maker
NEW LISTING! Flamingo Bay Cottage (3-Bedroom) with Pool - Pets Allowed by RedAwning
8.0 out of 10, Very Good, (2)
"While many homes in this neighborhood are still struggling to recover from hurricane Ian, this cozy litte place is primed for the tourist season! Recently updated with very pretty, Florida decor, and sitting right on the canal for easy access to the gulf, our time spent here was relaxing and pleasant indeed. One thing to note is, it may not be a good fit for an older person who is prone to falls. I care for my mom, and would not have wanted to bring her here, as most of the rooms are on...
NEW LISTING! Flamingo Bay Cottage (3-Bedroom) with Pool - Pets Allowed by RedAwning
Fridge, microwave, oven, stovetop
🔆🏝LITTLE PARADISE🏝🔆
10.0 out of 10, Exceptional, (29)
"Nice place very comfortable. Enjoyed pool and golf cart."
🔆🏝LITTLE PARADISE🏝🔆
Outdoor pool
The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (549)
"Full kitchen, nice living room, dining area, 2 nice sized bedrooms with comfortable beds. Nice beds. View of the Peace river and dock from balcony."
The price is $169
$189 total
includes taxes & fees
May 27 - May 28
The Suites at Fishermen’s Village- 2 Bedroom Suites
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Beach/ocean view
Edison Beach House
3.5 star property
9.4 out of 10, Exceptional, (1079)
"Vending machine would be helpful "
The price is $207
$231 total
includes taxes & fees
May 28 - May 29
Edison Beach House
Grand Studio Suite, Kitchenette | Living area | Smart TV
Lazy Cuckoo Inn
3.5 star property
8.8 out of 10, Excellent, (126)
"Very clean and peaceful. I highly recommend this company for vacation rental"
Lazy Cuckoo Inn
Balcony view
Lovers Key Resort
3.0 star property
8.8 out of 10, Excellent, (931)
"Absolutely Love this place! Clean, beautiful condo with an amazing view. "
The price is $170
$349 total
includes taxes & fees
Jun 4 - Jun 5
Lovers Key Resort
Lobby
Hyatt Vacation Club at Coconut Cove, Bonita Springs
4.0 star property
9.2 out of 10, Wonderful, (405)
"The property was pretty and had a lot to offer. We thought there would be more events for kids, but none really happened. The most frustrating part was the pool and bar closing so early! We went on excursions during the day then couldn't come enjoy a drink and the pool at night. "
The price is $274
$333 total
includes taxes & fees
May 27 - May 28
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Interior
TROPICAL HOUSE WITH POOL
9.6 out of 10, Exceptional, (7)
"I thoroughly enjoyed staying at this beautiful property. It was very nicely upgraded with very comfortable beds. The master bathroom was awesome! The shower had great water pressure! Its located close to many conveniences in downtown Cape Coral. The property manager was very accomodating with my requests. If I’m in the area anytime, I will definitely return to this property."
The price is $130
$352 total
includes taxes & fees
May 29 - May 30
TROPICAL HOUSE WITH POOL
Beach | On the beach, sun loungers, beach towels
FULLY RESTORED! Rare Walkout Condo On Sanibel Beach
10.0 out of 10, Exceptional, (74)
"The address we were given, 3401, was/is incorrect. We were not given the name of the condo units, and once found, realized there was no signage. I called the property manager for info and was told they did not speak English, unfortunately we were not bi-lingual. We recognized the condo from the photo. Two other guests also had the same problem. Including written check out info at the condo would be helpful. After finally finding the condo, however, our stay was excellent. We would definitely...
FULLY RESTORED! Rare Walkout Condo On Sanibel Beach
Outdoor pool
GullWing Beach Resort
3.5 star property
9.6 out of 10, Exceptional, (869)
"I was unaware it would have been helpful to rent a car due to its location. The area and building was still under construction. Noisy during the week. No restaurant or food in the building. Store was 1 1/2 miles away so on first day I had not way to buy food until I rented a bike the next day. Or rent an Uber. Condo was amazing!! Beach front. Clean and large open concept. Large balcony. Would have been great if they also provided beach chairs and umbrella instead of having to rent...
GullWing Beach Resort
Dock
Matlacha Tiny Village
3.0 star property
8.8 out of 10, Excellent, (229)
"We had a very nice stay at the tiny house! (Keep in mind, it is tiny) But very comfortable!! An unique experience and the property was outstanding compared to all the other units in the vicinity. It had a nice spacious canal front deck, and kayaks with a launching deck. Complete mini kitchen and great coffee preps. The beds were very comfortable and unit was very clean and updated. Decorated nicely! Loved the loft! Great alternative to a hotel room. We would definitely stay at Matlacha Tiny...
The price is $138
$229 total
includes taxes & fees
May 27 - May 28
Matlacha Tiny Village
Pool | A heated pool
Twin House shared Volleyball pool 3 King bedrooms, 2 sofa sleepes 8
8.6 out of 10, Excellent, (57)
"This was a great property. The pool was amazing and overall accomodations were wonderful. Location was good on beautiful canal. Only drawback was it was close to busy road."
Twin House shared Volleyball pool 3 King bedrooms, 2 sofa sleepes 8
Pool | Outdoor pool, a heated pool
Pool Villa 'Coral Sunburst' Cape Coral, FL
8.8 out of 10, Excellent, (16)
"Great location. Spacious living area. Grand kids loved the pool."
Pool Villa 'Coral Sunburst' Cape Coral, FL
Beach | On the beach
Amazing location! Beachfront Island Cottage On The Gulf "Old" FL still exists!!
9.4 out of 10, Exceptional, (84)
"I love this cottage. Very clean and comfortable Thank you Angelo for everything!"
Amazing location! Beachfront Island Cottage On The Gulf "Old" FL still exists!!
Terrace/patio
New to Market! Spacious Beach Retreat, Steps to Sugary Sand, Conveniences and Fun!
7.8 out of 10, Good, (30)
"The screened in porch was so nice to take our morning coffee to. Plenty of room in the kitchen for two cooks. My daughter in law is waiting on a heart and I wanted to take her on this trip to Florida This house was clean and spacious Met our neighbor across the street and he was so nice"
New to Market! Spacious Beach Retreat, Steps to Sugary Sand, Conveniences and Fun!
Pool | A heated pool
Waterfront Villa Sophie - rehabilitated after hurricane
9.8 out of 10, Exceptional, (89)
"Very good holiday overall. Disappointing the kayak couldn’t be used,also lots of ants around the pool. However we still enjoyed ourself."
Waterfront Villa Sophie - rehabilitated after hurricane
Smart TV, video games, DVD player, books
Pool home, 4 bedroom/ 3bath in a great location in Cape Coral!
10.0 out of 10, Exceptional, (64)
"We had such a wonderful stay......very clean, extremely well stocked with everything you need, including beach chairs, all kinds of utensils, spices etc.......great layout of the bedrooms for privacy if you need, nice pool, and responsive host. Highly recommend it!"
Pool home, 4 bedroom/ 3bath in a great location in Cape Coral!
Pool | Outdoor pool, a heated pool
Modern Villa - Waterfront w/Gulf Access, huge Pool and Spa, centrally located
9.8 out of 10, Exceptional, (132)
"Loved the house and pool! The property manager Anya was wonderful too!!"
Modern Villa - Waterfront w/Gulf Access, huge Pool and Spa, centrally located
Beach
Privacy in Paradise
10.0 out of 10, Exceptional, (58)
"Heat place to stay and anchor our adventures from. Thank you!"
Privacy in Paradise
On the beach
SANIBEL SUN CASTLE - Splendid home, great location, heated pool, bike to beach
9.8 out of 10, Exceptional, (83)
"Ralph and Ana are amazing hosts providing amenities for a perfect beach house experience. We were able to enjoy the home/pool and did several local excursions. Cabbage Key was fun. Bowman's Beach has to be one of the nicest, cleanest, and uncrowded beaches in the US- what a treat. We enjoyed the peaceful neighborhood walks in the evenings and at dawn. I highly recommend this place!"
SANIBEL SUN CASTLE - Splendid home, great location, heated pool, bike to beach
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See all available properties in Pine Island
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.

Pine Island Vacation Rental Travel Info

Vacation rentals
18
Popular accommodation
Pine Island private vacation homes
International airport
Fort Myers, FL (RSW-Southwest Florida Intl.)

Other types of properties in Pine Island you may be interested in

Studio | Individually decorated, individually furnished, free WiFi, bed sheets
Off the Charts Inn & Out Island Resort
2.5 star property
9.6 out of 10, Exceptional, (126)
"Great hang. "
Off the Charts Inn & Out Island Resort
2 outdoor pools, open 8:00 AM to 8:30 PM, cabanas (surcharge)
Sunseeker Resort Charlotte Harbor
4.0 star property
9.4 out of 10, Exceptional, (225)
"Friendliness, clean, new"
The price is $186
$242 total
includes taxes & fees
May 27 - May 28
Sunseeker Resort Charlotte Harbor
Outdoor pool
Margaritaville Beach Resort Fort Myers
4.0 star property
8.8 out of 10, Excellent, (300)
"We loved hanging out at the pool. The DJ was really good. We also loved being able to support the local vendors as Ft. Myers Beach."
The price is $319
$395 total
includes taxes & fees
Jun 9 - Jun 10
Margaritaville Beach Resort Fort Myers
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.

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 $130 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.

Recent reviews of Pine Island properties
Expedia verified reviews

Sanibel Island Beach Resort

Sanibel Island Beach Resort

5/5 Excellent
"Staff was great. Delicious food on premise. Pool was amazing. "
A verified traveler stayed at Sanibel Island Beach Resort
Posted 22 hours ago
Sanibel Island Beach Resort