Pine Island Vacation Rentals from CA $100: Short-Term Rentals for 2026

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Our top choices for Pine Island vacation rentals

A beach with a prominent dead tree trunk, sandy shore, and calm sea.

1. MALU LANI Inn & Marina

Bokeelia

April

CA $552 total

includes taxes & fees

Nov 18 - Nov 19

A beachside area with colorful beach houses, a dock, and a sandy beach.

2. Matlacha Tiny Village

Matlacha

Shannon

CA $314 total

includes taxes & fees

Nov 15 - Nov 16

3. Sundial Beach Resort & Spa

Mid Island

Jeremy

CA $642 total

includes taxes & fees

Nov 29 - Nov 30

A beach with a view of the ocean and a sunset.

4. Island Inn

West End

Nicole

CA $345 total

includes taxes & fees

Nov 12 - Nov 13

A balcony with a TV, a chair, and a view of a beach with a pier.

5. Edison Beach House

Fort Myers Beach

Joshua

CA $297 total

includes taxes & fees

Nov 17 - Nov 18

A spacious living room with a grey sofa, striped armchair, and a woven coffee table. Large windows offer a view of a tropical garden.

6. Driftwood Inn

Mid Island

Terri

CA $646 total

includes taxes & fees

Nov 15 - Nov 16

A modern hotel room with a kitchenette, a bed, a seating area, and a wardrobe.

7. StudioRes by Marriott Fort Myers Airport

Fort Myers

Joseph

CA $112 total

includes taxes & fees

Nov 16 - Nov 17

A beach with a clear sky, palm trees, and a sunlit ocean.

8. GullWing Beach Resort

South Island

Jennifer

CA $792 total

includes taxes & fees

Dec 2 - Dec 3

A modern living room with a flat-screen TV, a floor lamp, a dining table, and a sofa.

9. Lazy Cuckoo Inn

Fort Myers Beach

Bruce

CA $139 total

includes taxes & fees

Nov 11 - Nov 12

A beach with a thatched-roof structure, palm trees, and a view of the sea.

10. The Suites at Fishermen’s Village

Punta Gorda Isles

John

CA $296 total

includes taxes & fees

Nov 30 - Dec 1

A balcony with wicker furniture, a bottle, and glasses, overlooking a sunset over a body of water and buildings.

11. Lovers Key Resort

Fort Myers Beach

Joanne

CA $418 total

includes taxes & fees

Nov 11 - Nov 12

A marina with boats docked, a bridge overhead, and buildings with outdoor seating.

12. Harbour House at the Inn 308

Fort Myers Beach

CA $728 total

includes taxes & fees

Dec 10 - Dec 11

A modern kitchen with a dining area, featuring a large glass table set for four, a ceiling fan, and a wall clock.

13. Private Pool! Game Room! Very Close to Downtown!

Hancock

CA $766 total

includes taxes & fees

Nov 11 - Nov 12

An outdoor seating area with wicker furniture and a thatched roof.

14. The Dex

Mid Island

Pablo

A sectional sofa with a chaise, a small table, and a wicker ottoman in an outdoor setting with a clear sky and palm trees.

15. Flamingo Inn

Mid Island

Emily

CA $250 total

includes taxes & fees

Nov 11 - Nov 12

A modern living room with a dining area, a grey sofa, a coffee table, and a wall clock.

16. Lakeside Oasis

Iona

CA $354 total

includes taxes & fees

Nov 11 - Nov 12

A beach with sand, palm trees, and a clear sky.

17. The Wren

Mid Island

Michael P

CA $773 total

includes taxes & fees

Nov 14 - Nov 15

A modern apartment with a dining area, kitchen, and living space.

18. Experience Elevated Living in Fort Myers

Fort Myers

CA $391 total

includes taxes & fees

Nov 11 - Nov 12

A modern kitchen with white cabinets, a black dining table, and chairs.

19. The Meridian 2825

Fort Myers

CA $427 total

includes taxes & fees

Nov 17 - Nov 18

A modern kitchen with white cabinetry, a central island, and stainless steel appliances.

20. Riverfront Home w Private Dock Pool Beaches

McGregor

CA $1,412 total

includes taxes & fees

Dec 7 - Dec 8

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Find vacation rentals that suit your style

Top Pine Island Hotel Reviews

A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a window with curtains.

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Caloosahatchee

10/10 Excellent

We had a wonderful stay at Holiday Inn Express Cape Coral. The hotel was very clean, comfortable, and well maintained. A special thank you to Molly at the front desk. She was incredibly friendly, welcoming, and helpful from the moment we arrived. She made us feel truly valued as guests. We would also like to recognize the wonderful lady working in the breakfast area. She kept everything clean, fresh, and well organized, and she was always kind and attentive. The breakfast was excellent, and her...

Isaura

A modern dining area with a central island, multiple tables, and chairs.

Fairfield Inn & Suites by Marriott Cape Coral/North Fort Myers

Hancock

10/10 Excellent

Yosleivy

A modern hotel lobby with a seating area, a reception desk, and a dining area.

Hampton Inn & Suites - Cape Coral/Fort Myers Area, FL

Caloosahatchee

10/10 Excellent

Kimberley

An outdoor patio with tables and chairs, umbrellas, and a pool in the background.

Holiday Inn Express & Suites Ft Myers Beach-Sanibel Gateway by IHG

Fort Myers Beach

10/10 Excellent

Carlton

A modern hotel lobby with a reception desk, seating area, and a dining section.

Holiday Inn Express & Suites Fort Myers Airport by IHG

Daniels Corridor

10/10 Excellent

Julio Cesar Gutierrez

A spacious dining area with multiple tables and chairs, large windows, and a modern chandelier.

Residence Inn by Marriott Fort Myers Sanibel

Fort Myers

10/10 Excellent

Handan

A spacious lobby with a high ceiling, a seating area with a sofa and chairs, a small round table, and a decorative wall with artwork.

Hampton Inn & Suites Fort Myers Beach/Sanibel Gateway

Fort Myers Beach

10/10 Excellent

George

A building entrance with a stone facade, a bench, and a water feature.

Holiday Inn Express & Suites Punta Gorda by IHG

Punta Gorda

10/10 Excellent

Front desk staff were very friendly and helpful. The breakfast attendant ladies were amazing - brought food out to our table and were very chatty and lovely. I think their names were Brianna and Uni? Breakfast was terrific: biscuits, gravy, scrambled eggs, bacon sausages, hash browns, cinnamon buns, yogurt, fresh fruit (apples bananas), variety of juices, coffee, milk and almond milk. The pancake machine was the only thing that was iffy - very lightly cooked them so they were still doughy (we...

Catherine

A modern dining area with wooden flooring, white chairs, and large windows offering a view of the beach.

Best Western Plus Beach Resort

Fort Myers Beach

10/10 Excellent

Grace Carolyn

A reception area with a modern design, featuring a wooden panel wall with integrated lighting, a reception desk, and a refrigerator stocked with beverages.

Comfort Suites Fort Myers East I-75

Fort Myers

10/10 Excellent

Glenn

A reception area with a modern design, featuring a reception desk, a wall-mounted information board, and a refrigerator stocked with beverages.

MainStay Suites Fort Myers East I-75

Fort Myers

10/10 Excellent

Shaun

A swimming pool with a rock arch structure, a multi-story building with balconies, and palm trees in the background.

Pink Shell Beach Resort and Marina

Fort Myers Beach

10/10 Excellent

Andre Wolfram

Find out more about Pine Island

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 $100 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.

Pine Island Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pine Island vacation rentals

1. MALU LANI Inn & Marina

2. Matlacha Tiny Village

3. Sundial Beach Resort & Spa

4. Island Inn

5. Edison Beach House

6. Driftwood Inn

7. StudioRes by Marriott Fort Myers Airport

8. GullWing Beach Resort

9. Lazy Cuckoo Inn

10. The Suites at Fishermen’s Village

11. Lovers Key Resort

12. Harbour House at the Inn 308

13. Private Pool! Game Room! Very Close to Downtown!

14. The Dex

15. Flamingo Inn

16. Lakeside Oasis

17. The Wren

18. Experience Elevated Living in Fort Myers

19. The Meridian 2825

20. Riverfront Home w Private Dock Pool Beaches

Find vacation rentals that suit your style

Top Pine Island Hotel Reviews

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

10/10 Excellent

Find out more about Pine Island

Pine Island vacation rentals: An excellent choice for every season

How to find incredible deals on Pine Island rentals

Explore a world of travel with Expedia