Pine Island Holiday 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

Holiday Rentals in Pine Island

Fridge, microwave, oven, stovetop
🔆🏝LITTLE PARADISE🏝🔆
10.0 out of 10, Exceptional, (29)
"Nice place very comfortable. Enjoyed pool and golf cart."
🔆🏝LITTLE PARADISE🏝🔆
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
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
Save an average of 15% on thousands of hotels when you're signed in
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, sun-loungers, beach towels
3/2 home on Little Gasparilla Island - Gulf of Mexico. Private beach and dock!
10.0 out of 10, Exceptional, (28)
"Our stay was fantastic from the first day to the last. John's home is welcoming and had everything we needed for our two week stay. The short walk to the beach was wonderful and you could hear the waves crashing the shoreline from the deck of the house. We will definitely be back!!"
3/2 home on Little Gasparilla Island - Gulf of Mexico. Private beach and dock!
Property grounds
Gulf Access Waterfront Large One or Two Bedroom In Law Suite
10.0 out of 10, Exceptional, (28)
"Everything was great. Place was clean, decorated nicely, very quiet neighborhood and a Great lanai!"
Gulf Access Waterfront Large One or Two Bedroom In Law Suite
Beach
New Owners! Just Renovated. Serenity and Shelling Oasis. Walk to the Beach.
10.0 out of 10, Exceptional, (22)
"Roomy comfortable home located in quiet area of Sanibel. Close to beach. East end location minimized traffic issues that plaque Sanibel every spring. Exceedingly well equipped. We prepared our meals 90% of the 3 week stay. Large fridge/freezer; very functional clean stove & oven. Would unconditionally recommend"
New Owners! Just Renovated. Serenity and Shelling Oasis. Walk to the Beach.
Outdoor pool
The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (529)
"Very clean. Two bedrooms design is great."
The price is AU$266
includes taxes & fees
22 May - 23 May
The Suites at Fishermen’s Village- 2 Bedroom Suites
Pool
Waterfront Villa Sophie - rehabilitated after hurricane
9.8 out of 10, Exceptional, (88)
"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
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
On the beach
SANIBEL SUN CASTLE - Splendid home, great location, heated pool, bike to beach
9.8 out of 10, Exceptional, (82)
"We loved our stay at Sanibel Suncastle! The house is as advertised but even better. The location is perfect. We really enjoyed the pool and the peaceful back porch. The family room was perfect for all of us to watch NCAA basketball games on the large tv. I would definitely stay at Ralph’s home again. It was a perfect long weekend getaway for our group of 3 couples."
SANIBEL SUN CASTLE - Splendid home, great location, heated pool, bike to beach
Pool
Waterfront Villa with unique view of wide canal and nature preserve - Pool & Spa
9.8 out of 10, Exceptional, (156)
"We absolutely loved everything about Villa Amara. Our hosts were incredibly kind and communicative and super helpful with all our questions. The villa is in a wonderful location in Cape Coral, and the house and the entire property is so well-kept, lovely, and homey. The view from the lanai and pool is stunning; we spent hours just sitting on the porch watching the water, trees, and birds. The house is beautifully appointed with everything guests could need for a comfortable stay. My husband and...
Waterfront Villa with unique view of wide canal and nature preserve - Pool & Spa
Property grounds
Spectacular Sunsets with Direct Gulf views, Pool,11th floor, Building C, WiFi
9.8 out of 10, Exceptional, (177)
"We enjoyed our stay at mikes condo we had awesome sunsets from the balcony loved the extra air conditioning in the bedroom it helped a lot to ke"
Spectacular Sunsets with Direct Gulf views, Pool,11th floor, Building C, WiFi
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 AU$532
includes taxes & fees
20 May - 21 May
TROPICAL HOUSE WITH POOL
Outdoor pool
GullWing Beach Resort
3.5 star property
9.6 out of 10, Exceptional, (868)
"It's basically a condo you're staying in with all the amenities of home."
GullWing Beach Resort
Outdoor pool, pool loungers
Resort Harbour Properties
3.5 star property
9.6 out of 10, Exceptional, (315)
"Wonderful view and beautiful condo. Only downside was the ocean water was not the cleanest but the pool made up for it "
Resort Harbour Properties
Beach/ocean view
Edison Beach House
3.5 star property
9.4 out of 10, Exceptional, (1067)
"Way more than we expected. Very nice."
The price is AU$367
includes taxes & fees
21 May - 22 May
Edison Beach House
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 Tiny House - INTRODUCTORY PRICE minutes from Sanibel and Fort Myers Beach!
9.4 out of 10, Exceptional, (16)
"This was a wonderful stay in a cute tiny home. Everything was very clean and we had a good time."
The price is AU$265
includes taxes & fees
20 May - 21 May
New Tiny House - INTRODUCTORY PRICE minutes from Sanibel and Fort Myers Beach!
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 AU$497
includes taxes & fees
29 May - 30 May
Hyatt Vacation Club at Coconut Cove, Bonita Springs
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 Holiday Home Travel Info

Holiday homes
18
Popular accommodation
Pine Island private holiday 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, pool cabanas (surcharge)
Sunseeker Resort Charlotte Harbor
4.0 star property
9.4 out of 10, Exceptional, (209)
"If you're seeking the ultimate getaway, look no further than this resort oasis. Nestled amidst lush, meticulously manicured grounds, this hotel offers a serene escape from the hustle and bustle of everyday life. From the moment you arrive, you're greeted with unparalleled hospitality from a team that's not just helpful, but genuinely friendly. One of the standout features is the abundance of culinary options. With multiple dining venues on-site, you'll embark on a culinary journey that delights...
The price is AU$362
includes taxes & fees
27 May - 28 May
Sunseeker Resort Charlotte Harbor
Outdoor pool
Margaritaville Beach Resort Fort Myers
4.0 star property
8.6 out of 10, Excellent, (278)
"I love it !"
The price is AU$504
includes taxes & fees
5 June - 6 June
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pine Island holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pine Island holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pine Island holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pine Island holiday rentals we have selected for you start as low as AU$266 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pine Island rentals

At Expedia, we put the best Pine Island holiday 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 holiday.

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