Pineland Vacation Rentals from $86: Search Short-Term Rentals

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Our top choices for Pineland vacation rentals

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

1. Matlacha Tiny Village

Matlacha

Lori

$213 nightly

Oct 15 - Oct 16

Total with taxes and fees

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

2. MALU LANI Inn & Marina

Bokeelia

Kyle

$330 nightly

Oct 15 - Oct 16

Total with taxes and fees

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

3. Island Inn

West End

Nicole

$247 nightly

Oct 17 - Oct 18

Total with taxes and fees

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

Dawn

$175 nightly

Oct 30 - Oct 31

Total with taxes and fees

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

5. Lazy Cuckoo Inn

Fort Myers Beach

Bruce

$77 nightly

Oct 26 - Oct 27

Total with taxes and fees

A beach view from a balcony with a pool, palm trees, and a building with a balcony.

6. Edison Beach House

Fort Myers Beach

Angie

$238 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

7. Sundial Beach Resort & Spa

Mid Island

Lisa Renee

$416 nightly

Oct 15 - Oct 16

Total with taxes and fees

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

Heather

$406 nightly

Oct 15 - Oct 16

Total with taxes and fees

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Top Pineland Hotel Reviews

Lani Kai Beachfront Resort

8/10 Good

"This resort is a little rough looking on the outside. Also was hit by hurricane ira, so they have done fantastic since then. Perfect for an elderly couple as far as easy access, just the most pleasant and helpful staff and bars and restaurants on site is perfect for us without a car. I would come back here just to be able to talk with the front desk staff!"

La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway

10/10 Excellent

"I absolutely loved it here at this hotel. I came here due to the pool and it did not disappoint. It’s a 22 m pool so I was able to do lapses. People complain. It was too cold, but I found the water actually warm. The only sad part is that I did not stay the entire week as it was hurricane season and I was not able to do anything due to the rain. Next time I will make sure to book when it’s not gray and rainy. Aside from that the rooms were a little muggy and humid due to the temperature outside but nothing the hotel can do anything about. It is definitely not a luxury hotel but it really worked well for me. The wonderful young man at the front desk with the red hair and blue eyes was so kind. They were able to give me a refund for the remaining days with no questions asked. The breakfast was stunning and delicious, the coffee in the lobby was wonderful. The breakfast room unlike many other hotel was large and spacious so you didn’t have to struggle to find a spot. I really wanna come back at this hotel but like I said, at better times with better weather I highly recommend this hotel as it is incredible deal for your budget. Keep in mind that the cab ride from airport to this hotel is about $50 as it’s not in the centre of town. There is a bus that runs nearby, but not that simple to get and stops running at certain times. Thank you to all the wonderful stuff at this hotel, even though my stay was short it was sweet"

Find out more about Pineland

Everything you need to know about Pineland 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 Pineland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Pineland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pineland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pineland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pineland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $86 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pineland rentals

At Expedia, we put the best Pineland 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 Pineland 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 Pineland 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 Pineland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

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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. Lazy Cuckoo Inn

6. Edison Beach House

7. Sundial Beach Resort & Spa

8. Driftwood Inn

9. Lakeside Oasis Fort Myers

10. Harbour House at the Inn 308

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

12. Dreams Away - Sleeps 10 Pool Golf Fun

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

14. Riverfront Home w Private Dock Pool Beaches

Find vacation rentals that suit your style

Top Pineland Hotel Reviews

Lani Kai Beachfront Resort

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

The Lighthouse Resort Inn & Suites

Pink Shell Beach Resort and Marina

Sanibel Island Beach Resort

Margaritaville Beach Resort Fort Myers

La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway

Marriott Sanibel Harbour Resort & Spa

Candlewood Suites Fort Myers Sanibel Gateway by IHG

Find out more about Pineland

Frequently asked questions

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