A wooden pier extending into calm water with a clear sky and distant land.

Pineland Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Pineland vacation rentals

A compact kitchen with a built-in seating area, a refrigerator, and a ceiling fan.

1. Matlacha Tiny Village

Matlacha

Lori

￥35,045 total

includes taxes & fees

Nov 8 - Nov 9

A waterfront patio with palm trees, a dock, and a boat.

2. MALU LANI Inn & Marina

Bokeelia

April

￥60,501 total

includes taxes & fees

Dec 7 - Dec 8

A covered outdoor area with a table and chairs, a ceiling fan, and a view of a beach with palm trees and a boat.

3. Island Inn

West End

Nicole

￥47,222 total

includes taxes & fees

Nov 30 - Dec 1

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

4. The Suites at Fishermen’s Village

Punta Gorda Isles

John

￥33,199 total

includes taxes & fees

Nov 30 - Dec 1

A compact kitchen with white appliances, a small dining area, and a living room with a sofa and a lamp.

5. Edison Beach House

Fort Myers Beach

mark

￥35,418 total

includes taxes & fees

Nov 9 - Nov 10

A pool area with lounge chairs and umbrellas, a beach with umbrellas and lounge chairs, and palm trees.

6. Sundial Beach Resort & Spa

Mid Island

Lisa Renee

￥64,612 total

includes taxes & fees

Nov 10 - Nov 11

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

7. Lazy Cuckoo Inn

Fort Myers Beach

Bruce

￥15,452 total

includes taxes & fees

Nov 8 - Nov 9

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

8. Driftwood Inn

Mid Island

Terri

￥72,027 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Hancock

￥85,489 total

includes taxes & fees

Nov 8 - Nov 9

An aerial view of a rooftop pool area with lounge chairs, a swimming pool, and a staircase leading to an upper deck.

10. Harbour House at the Inn 308

Fort Myers Beach

￥80,529 total

includes taxes & fees

Dec 7 - Dec 8

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

11. Lakeside Oasis

Iona

￥39,382 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with a central island, stainless steel appliances, and a ceiling fan.

12. Dreams Away - Sleeps 10 Pool Golf Fun

Oakland Hills

￥57,260 total

includes taxes & fees

Nov 12 - Nov 13

A modern kitchen with white cabinets, a stainless steel refrigerator, and a ceiling fan.

13. 3 Mi to Fort Myers Beach! Family Getaway w/ Pool

Iona

￥69,302 total

includes taxes & fees

Dec 1 - Dec 2

A living room with a sectional sofa, a rug, a framed picture, and a door leading to another room.

14. Fort Myers Escape Near Downtown & Beach w/ Parking

Fort Myers

￥69,532 total

includes taxes & fees

Nov 8 - Nov 9

A modern kitchen with white cabinets, a stainless steel refrigerator, and a flat-screen TV mounted on the wall.

15. Beach Days & Backyard Nights! Fort Myers Retreat

Harlem Heights

￥52,890 total

includes taxes & fees

Nov 25 - Nov 26

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

16. Riverfront Home w Private Dock Pool Beaches

McGregor

￥159,128 total

includes taxes & fees

Nov 30 - Dec 1

View all properties

Find vacation rentals that suit your style

Top Pineland Hotel Reviews

A beachside area with colorful Adirondack chairs, a fire pit, and a view of the water.

Matlacha on Shoreview

Cape Coral

10/10 Excellent

Upon arrival room was ready. We received the room we booked, lower level, one bedroom suite poolside with screen porch. It was clean, cool, and ready for occupants. The area was very safe and the property was very well maintained and quiet. We liked fishing from the dock and caught quite a variety of fish. We would definitely stay there again. In addition they had very good internet and a nice large TV which my husband was able to enjoy football.

Pamela

MALU LANI Inn & Marina

Bokeelia

10/10 Excellent

Kyle

A turquoise building with a red door, surrounded by potted plants and flowers.

Angler's Inn

Matlacha

10/10 Excellent

Evelyn

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

Raydel

Matlacha Tiny Village

Matlacha

10/10 Excellent

Nikki

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

Lina

A balcony with a table and chairs, large windows, and a view of the sea.

The Westin Cape Coral Resort At Marina Village

Pelican

10/10 Excellent

danica

A balcony with a wooden table and chairs, a hanging chair, and a view of palm trees and a pool.

Off the Charts Inn & Out Island Resort

Saint James City

10/10 Excellent

The property was in the middle of a remodel so there were only 5 rooms available which made it very quiet. The unit was very clean. The amazing thing about the property was the canal in the back. The manatees were swimming around everyday. They were awesome to see. One evening there were dolphins playing in the canal. There was a great restaurant within walking distance that had great food, drinks and live music every night.

Bobbie

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

Jack

A spacious living room with a large flat-screen TV, a ceiling fan, and a view of the ocean through large windows.

South Seas

Captiva

10/10 Excellent

Our time at South Seas was great! Yes they are still rebuilding some areas and adding on more amenities, but we still had a great time. We stayed at a beach villa which was i. Pristine condition and very comfortable for our family of four. The marina side pools and slides were very fun and in great shape. The service we recieved was top notch. We were also provided a smores kit upon check in for the kids to use at their fire pit at night. Highly recommend this resort on Captiva.

Brandon

A resort with multiple-story buildings, palm trees, and a well-maintained lawn.

Sanibel Island Beach Resort

Mid Island

10/10 Excellent

Linda

The Suites at Fishermen’s Village

Punta Gorda Isles

10/10 Excellent

scott

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

I would stay here again in a minute! Conveniently located just off Fort Myers Beach, next to Walmart, bus station, and main highway. Staff was exceptional with kindness and immediate response to requests. Hotel is clean clean clean! Breakfast was yummy and had different choices daily. I’m a late breakfast eater so having a refrigerator and microwave in my room was convenient for heating breakfast up later in morning after grabbing it early. Book here..you won’t be sorry!

Dennette

A modern kitchen area with a breakfast bar, fruit display, and a chalkboard menu.

Hampton Inn Fort Myers Downtown

Fort Myers River District

10/10 Excellent

The property was very updated and clean. It had a warm breakfast breakfast buffet every morning eggs, bacon, waffles, bagels, toast, fruit, yogurt and juices. Enough to get you by until lunch. Staff was very friendly and helpful with any questions that I had. The only negative thing that I have to say is that I was there for four nights and housekeeping only came in once. However, I highly recommend this hotel.

Rhonda

A nighttime view of a bar with a pool in front.

Dolphin Key Resort

Caloosahatchee

10/10 Excellent

Clint

A resort with a central pool, multiple lounge areas, and a beach view.

Tween Waters Island Resort & Spa

Captiva

10/10 Excellent

Jim

Find out more about Pineland

Search for holiday rentals in Pineland on Expedia! You can easily find your home rentals, villas, holiday apartments in Pineland using one of the methods below:

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Frequently Asked Questions

Can I find vacation rentals in Pineland?

Yes, you can find vacation rentals close to well known points of interest in Pineland, or you can select a secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Pineland?

Tiki Hut Paradise 4-bedroom Bokeelia House w Golf Cart Tesla Charger Island Time: This Pineland vacation home rental has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Pineland?

Expedia has 9 vacation rentals for your stay in Pineland.

What can I see and do in Pineland?

While exploring the area, visit family-friendly sights like Sun Splash Water Park, or get outside and enjoy nature at Calusa Heritage Trail. In the larger area, you’ll find Randell Research Center and Useppa Island.

What are vacation rentals like in Pineland?

Vacation rentals are privately owned properties you can book for a couple days or more in Pineland. Vacation rentals offer extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family gatherings.

Pineland Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pineland vacation rentals

1. Matlacha Tiny Village

2. MALU LANI Inn & Marina

3. Island Inn

4. The Suites at Fishermen’s Village

5. Edison Beach House

6. Sundial Beach Resort & Spa

7. Lazy Cuckoo Inn

8. Driftwood Inn

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

10. Harbour House at the Inn 308

11. Lakeside Oasis

12. Dreams Away - Sleeps 10 Pool Golf Fun

13. 3 Mi to Fort Myers Beach! Family Getaway w/ Pool

14. Fort Myers Escape Near Downtown & Beach w/ Parking

15. Beach Days & Backyard Nights! Fort Myers Retreat

16. Riverfront Home w Private Dock Pool Beaches

Find vacation rentals that suit your style

Top Pineland Hotel Reviews

Matlacha on Shoreview

10/10 Excellent

Find out more about Pineland

Frequently Asked Questions

Can I find vacation rentals in Pineland?

What are some of the best vacation rentals in Pineland?

How many vacation rentals are there in Pineland?

What can I see and do in Pineland?

What are vacation rentals like in Pineland?