Pine Island Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

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, (546)
"I have stayed at this location at least a dozen times over the past few years. The staff is excellent. The rooms are clean but the building itself is in need of repair. Some of the upper floors appear treacherous-some had construction supports while I was last there. Rugs are covering upper walkways that are in need of stain etc. Several restaurants have closed on the property so options there are dwindling. Still plenty of boutiques left if you like to shop. The rooms are great, I love that...
The price is CA $232
CA $259 total
includes taxes & fees
May 27 - May 28
The Suites at Fishermen’s Village- 2 Bedroom Suites
Save an average of 15% on thousands of hotels when you're signed in
Beach/ocean view
Edison Beach House
3.5 star property
9.4 out of 10, Exceptional, (1076)
"Vending machine would be helpful "
The price is CA $295
CA $329 total
includes taxes & fees
Jun 3 - Jun 4
Edison Beach House
Grand Studio Suite, Kitchenette | Living area
Lazy Cuckoo Inn
3.5 star property
8.8 out of 10, Excellent, (125)
"Nice and clean with plenty of room"
Lazy Cuckoo Inn
Balcony view
Lovers Key Resort
3.0 star property
8.8 out of 10, Excellent, (930)
"Enjoyed the facility Area is still in recovery from Ian. Dining in area wasvery limited"
The price is CA $220
CA $462 total
includes taxes & fees
May 28 - May 29
Lovers Key Resort
Lobby
Hyatt Vacation Club at Coconut Cove, Bonita Springs
4.0 star property
9.2 out of 10, Wonderful, (403)
"The property is nice. Staff at front desk need to improve their servicd"
The price is CA $373
CA $454 total
includes taxes & fees
May 29 - May 30
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 CA $178
CA $482 total
includes taxes & fees
May 29 - May 30
TROPICAL HOUSE WITH POOL
Outdoor pool
GullWing Beach Resort
3.5 star property
9.6 out of 10, Exceptional, (869)
"It's basically a condo you're staying in with all the amenities of home."
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 CA $189
CA $313 total
includes taxes & fees
May 27 - May 28
Matlacha Tiny Village
Beach
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
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
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
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)
"Relaxing trip with close proximity to the beach."
New to Market! Spacious Beach Retreat, Steps to Sugary Sand, Conveniences and Fun!
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
Charming Cape Cottage, 4 bedroom/3 bath private pool in Cape Coral SW Florida
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!"
Charming Cape Cottage, 4 bedroom/3 bath private pool in Cape Coral SW Florida
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)
"Our family of 7 thoroughly enjoyed our stay at the Sanibel Sand Castle. The house was spacious, never feeling crowded, and had everything we could have needed. Our host Ralph was only a phone call away and was super helpful with any questions we had. The backyard with the pool was our absolute favorite! Can't wait to return."
SANIBEL SUN CASTLE - Splendid home, great location, heated pool, bike to beach
Don't see what you're looking for?
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
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, (219)
"We really enjoy this resort. This is a new facility right on the water. They offer about 11 restaurants and several bars. They even offer a small convenience store. Once you arrive, you never need to leave. Find a massive pool at the ground floor and for $20, use the pool club on the roof. Beautiful views of the harbor, sunset, bar & restaurant on the roof. We really don’t want too many folks to know about our new favorite place but we can’t keep it a secret. Absolutely fantastic facility. They...
The price is CA $255
CA $331 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, (294)
"First time, we we’re absolutely amazed, how nice and beautiful everything was done, the walking areas, pool, our room was clean and comfortable, definitely will be back!"
The price is CA $396
CA $495 total
includes taxes & fees
Jun 17 - Jun 18
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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pine Island vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pine Island vacation rentals we have selected for you start as low as CA $178 per night. Entering your travel dates in the search wizard 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