Pine Island Holiday Rentals

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Holiday Rentals in Pine Island

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...
Flamingo Bay Cottage (3-Bedroom) with Pool - Pets Allowed by RedAwning

🔆🏝LITTLE PARADISE🏝🔆

10.0 out of 10, Exceptional, (29)
"Nice place very comfortable. Enjoyed pool and golf cart."
🔆🏝LITTLE PARADISE🏝🔆

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (698)
"Very enjoyable stay!"
The price is AU$651
includes taxes & fees
3 Jan - 4 Jan 2025
The Suites at Fishermen’s Village- 2 Bedroom Suites

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4.0 star property
9.2 out of 10, Wonderful, (490)
"This property is incredible. We had such a wonderful stay. The room was phenomenal. The facilities were beyond wonderful. Our family had a great trip "
The price is AU$495
includes taxes & fees
14 Jan - 15 Jan 2025
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Edison Beach House

3.5 star property
9.4 out of 10, Exceptional, (1218)
"Great stay, very good Hotel Suite style with great location, parking ect."
The price is AU$473
includes taxes & fees
12 Jan - 13 Jan 2025
Edison Beach House

Lazy Cuckoo Inn

2.0 star property
9.0 out of 10, Wonderful, (152)
"Spotless…no carpet in either B/R, or kitchen area. Medium size fridge with a good sized freezer section. Appliances include coffee maker (Keurig pods), toaster, kettle, induction cooker. Plates, bowls, glasses, mugs, cutlery, utensils, dish cloth, dish towels, dishwashing detergent are onsite. Large - 6ft or wider - closet. Walmart and Publix are nearby. Beach trolley with free parking is about 1/2 mile away"
The price is AU$251
includes taxes & fees
3 Jan - 4 Jan 2025
Lazy Cuckoo Inn

Lovers Key Resort

3.0 star property
8.8 out of 10, Excellent, (958)
"The bridge. Construction is very loud "
The price is AU$711
includes taxes & fees
2 Jan - 3 Jan 2025
Lovers Key Resort

GullWing Beach Resort

3.5 star property
9.6 out of 10, Exceptional, (897)
"The apartment was impeccable. Clean and with all the needed things. "
The price is AU$1,079
includes taxes & fees
4 Jan - 5 Jan 2025
GullWing Beach Resort

TROPICAL HOUSE WITH POOL

9.6 out of 10, Exceptional, (15)
"Very nice house and property! Great location Clean Owner was very quick to respond to any questions "
TROPICAL HOUSE WITH POOL

FULLY RESTORED! Rare Walkout Condo On Sanibel Beach

10.0 out of 10, Exceptional, (83)
"Of course the area was not pristine but they have been thru alot of hurricanes and besides we weren't there to admire the grounds. We found shells larger than ever found. The beach is covered with them. There were really good places to eat. Timbers was a favorite. There is easy access to a nice pool. The rooms were very clean. Decorations very nice. Totally enjoyed it. Communication so easy and supportive -- even for an old techno dummie like me. Totally appreciated."
FULLY RESTORED! Rare Walkout Condo On Sanibel Beach

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

Matlacha Tiny Village

3.0 star property
8.8 out of 10, Excellent, (238)
"Quiet area and great little houses. Rented the margarita and was not disappointed. At one point our door lock failed and the manager was there within a few minutes to fix it. Would stay again!"
The price is AU$390
includes taxes & fees
31 Dec - 1 Jan 2025
Matlacha Tiny Village

Pool Villa 'Coral Sunburst' Cape Coral, FL

8.6 out of 10, Excellent, (17)
"Overall quiet easy stay."
The price is AU$835
includes taxes & fees
13 Jan - 14 Jan 2025
Pool Villa 'Coral Sunburst' Cape Coral, FL

Spacious Beach Retreat, Steps to Sugary Sand, Conveniences and Fun!

7.6 out of 10, Good, (41)
"No complaints about property itself, it was good for that price. The issue that we had was quickly resolved by management. Kids were not happy with the beach quality, but there are better options available with an hour driving."
Spacious Beach Retreat, Steps to Sugary Sand, Conveniences and Fun!

Waterfront Villa Sophie - rehabilitated after hurricane

9.8 out of 10, Exceptional, (96)
"My bride and I both really like the home, We felt comfortable and the place had a warm feeling. We had stayed in larger homes but this place was great. We would consider renting this home again in the future. The Property manager was very friendly and easy going."
Waterfront Villa Sophie - rehabilitated after hurricane

Enjoy your family time at spacious Villa Alica with Pool, Spa & Outdoor Kitchen

9.8 out of 10, Exceptional, (136)
"Our family had a great time at this property over the 2024 Thanksgiving holiday. The house was very clean, well supplied (towels, kitchen supplies, etc.) and is in a great location with easy access to stores, restaurants, roadways, etc. All the TVs, appliances, pool, hot tub, washer/dryer, etc. worked propoerly - no technical problems. Communications with the property owners was easy and they were very responsive, as we the local property manager. We would definitely consider staying at this...
Enjoy your family time at spacious Villa Alica with Pool, Spa & Outdoor Kitchen

Pool home, 4 bedroom/ 3bath in a great location in Cape Coral!

9.8 out of 10, Exceptional, (67)
"Property and house was nice. The pool area was private. Our only complaint was reading all the rules they had written down that you are supposed to follow. Example, completely clean the grill or be charged $100. We decided not to use it. Everything needs to be exactly where it was. You are told you need to do some cleaning while there. While I'm sure everyone does that don't like being told I have to. Also says all towels should be cleaned the morning you leave except one dirty one for each...
Pool home, 4 bedroom/ 3bath in a great location in Cape Coral!

Privacy in Paradise

10.0 out of 10, Exceptional, (62)
"The property was more beautiful than we expected. There was more than enough space to lounge eat or relax. It was so clean we didn’t use the linens or pillows we brought with us. Anything we forgot to bring was in the pantry! And which host leaves us sodas, water and a bottle of great wine?… Richard! We didn’t want to leave and have decided to return in the spring, summer and fall next year. Thanks for treating us so well. Bravo Paradise!!"
Privacy in Paradise

SANIBEL SUN CASTLE - Splendid home, great location, heated pool, bike to beach

9.8 out of 10, Exceptional, (88)
"Ralph was the most responsive and helpful host I have ever dealt with in all the years I have been using VRBO and other on line rental sites. Pool was great and view was amazing. Close to many things in Sanibel which of course is a great island and recovering from the storms but still has its charm."
SANIBEL SUN CASTLE - Splendid home, great location, heated pool, bike to beach

Resort Harbour Properties

3.5 star property
9.6 out of 10, Exceptional, (329)
"Our rental unit was perfect. Very well supplied and very clean. The screened balcony was a very nice addition to the unit abd the views were superb!"
Resort Harbour Properties
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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Other types of properties in Pine Island you may be interested in

Off the Charts Inn & Out Island Resort

2.5 star property
9.6 out of 10, Exceptional, (129)
"I love the boat docks and ease of access . When I am on Pine Island , this is the only place we stay . "
Off the Charts Inn & Out Island Resort

Marriott Sanibel Harbour Resort & Spa

4.0 star property
8.4 out of 10, Very good, (1003)
"You are right by the Sanibel bridge. "
The price is AU$684
includes taxes & fees
31 Dec - 1 Jan 2025
Marriott Sanibel Harbour Resort & Spa

Margaritaville Beach Resort Fort Myers

4.0 star property
8.8 out of 10, Excellent, (723)
"Immaculate vibes"
The price is AU$557
includes taxes & fees
5 Jan - 6 Jan 2025
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.