Pine Island Holiday Rentals

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Holiday 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, (550)
"Fully equipped condo set up. Very clean and comfortable. Employees were very helpful. If they could screen in the balconies it would be great as bugs and birds make it uncomfortable."
The price is NZ$290
per night
10 Jun - 11 Jun
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, (1080)
"Found this property by chance. What a find!! So happy we did! Only a one night stay as we were traveling through but oh wish we could stay longer. We will be back! Thank you Ms. Annie for a warm welcome and thorough run down on the amenities (which includes beach chair/pool toy/umbrella closet for property guests- what a nice surprise 😃) The surrounding area is still very much in the recovery process from the recent hurricane hit, no fault of Edison. Neat, relaxed beach town feel- not too...
The price is NZ$377
per night
28 May - 29 May
Edison Beach House
Grand Studio Suite, Kitchenette | Living area
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 NZ$528
per night
28 May - 29 May
Lovers Key Resort
Lobby
Hyatt Vacation Club at Coconut Cove, Bonita Springs
4.0 star property
9.2 out of 10, Wonderful, (405)
"nice place"
The price is NZ$498
per night
28 May - 29 May
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 NZ$575
per night
29 May - 30 May
TROPICAL HOUSE WITH POOL
Beach
FULLY RESTORED! Rare Walkout Condo On Sanibel Beach
10.0 out of 10, Exceptional, (75)
"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)
"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, (230)
"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 NZ$374
per night
28 May - 29 May
Matlacha Tiny Village
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)
"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
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
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.

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, (232)
"Friendliness, clean, new"
The price is NZ$366
per night
30 May - 31 May
Sunseeker Resort Charlotte Harbor
Outdoor pool
Margaritaville Beach Resort Fort Myers
4.0 star property
8.8 out of 10, Excellent, (305)
"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 NZ$506
per night
4 Jun - 5 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Pine Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Pine Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Pine Island. Seeing all the best attractions is bound to make you fall in love with Pine Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Pine Island short-term rentals, that won’t be hard to do.

Recent reviews of Pine Island properties
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