A waterfront with palm trees and a boat dock.

Pineland Vacation Rentals

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Our top choices for Pineland vacation rentals

1. MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Overall, very friendly Gave me advice about the area Told me what live bands were playing that night Very fun definitely will be back"
United States
Kyle
The price is CA $276
CA $560 total
includes taxes & fees
Aug 3 - Aug 4
MALU LANI Inn & Marina

2. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (292 reviews)
"Very nice alternative to a motel quite clean everything you need for your stay. highly recommend this property"
United States
PETER
The price is CA $152
CA $275 total
includes taxes & fees
Aug 25 - Aug 26
Matlacha Tiny Village

3. Canalfront St James City Home w/ Unique View

Canalfront St James City Home w/ Unique View
3.0 star property
Saint James City
The price is CA $177
CA $485 total
includes taxes & fees
Aug 2 - Aug 3
Canalfront St James City Home w/ Unique View

4. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (295 reviews)
"Clean room, good location, easy check in instructions."
United States
Brooklyn
The price is CA $81
CA $136 total
includes taxes & fees
Aug 6 - Aug 7
Lazy Cuckoo Inn

5. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,142 reviews)
"Loved the location. Check in was smooth. Our room was ready when we got there even though we were early. Our room was lovely and had everything we needed. We thoroughly enjoyed our stay."
United States
Nellie
The price is CA $335
CA $373 total
includes taxes & fees
Aug 23 - Aug 24
Island Inn

6. Sleeps 16 Plus Central Cape Coral Family Escape 4 Bedroom Home

Sleeps 16 Plus Central Cape Coral Family Escape 4 Bedroom Home
3.0 star property
Hancock
The price is CA $212
CA $828 total
includes taxes & fees
Aug 2 - Aug 3
Sleeps 16 Plus Central Cape Coral Family Escape 4 Bedroom Home

7. The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,278 reviews)
"Really cute and calm beautiful place to stay."
United States
Maria
The price is CA $245
CA $275 total
includes taxes & fees
Aug 18 - Aug 19
The Suites at Fishermen’s Village- 2 Bedroom Suites

8. Hibiscus House Bed Breakfast Inn Flamingo Suite

Hibiscus House Bed Breakfast Inn Flamingo Suite
2.0 star property
Fort Myers River District
10.0 out of 10, Exceptional, (1 review)
The price is CA $209
CA $313 total
includes taxes & fees
Aug 4 - Aug 5
Hibiscus House Bed Breakfast Inn Flamingo Suite

9. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,838 reviews)
"I love this place, my favorite place to vacations."
United States
Johanna
The price is CA $232
CA $314 total
includes taxes & fees
Aug 3 - Aug 4
Edison Beach House

10. Driftwood Inn

Driftwood Inn
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (11 reviews)
"The cottage was well stocked with all we needed. It was also immaculate with a lovely garden. The beach was a 5 minute walk."
United States
Maureen
The price is CA $285
CA $655 total
includes taxes & fees
Aug 4 - Aug 5
Driftwood Inn

11. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,678 reviews)
"Clean room and beach view"
United States
Carla
The price is CA $531
CA $668 total
includes taxes & fees
Aug 3 - Aug 4
Sundial Beach Resort & Spa

12. Beach Days & Backyard Nights! Fort Myers Retreat

Beach Days & Backyard Nights! Fort Myers Retreat
3.0 star property
Harlem Heights
The price is CA $108
CA $455 total
includes taxes & fees
Aug 3 - Aug 4
Beach Days & Backyard Nights! Fort Myers Retreat

13. Hibiscus House Bed Breakfast Inn Turtle Room Bed-ada

Hibiscus House Bed Breakfast Inn Turtle Room Bed-ada
2.0 star property
Fort Myers River District
10.0 out of 10, Exceptional, (2 reviews)
"We had a lovely time enjoyed the staff and the end Keeper Lisette. Everything was great. We’ll stay again."
United States
Katherine
The price is CA $206
CA $310 total
includes taxes & fees
Aug 25 - Aug 26
Hibiscus House Bed Breakfast Inn Turtle Room Bed-ada

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

Fort Myers Escape Near Downtown & Beach w/ Parking
3.0 star property
Fort Myers
The price is CA $101
CA $399 total
includes taxes & fees
Aug 3 - Aug 4
Fort Myers Escape Near Downtown & Beach w/ Parking

15. Tropical Mango Grove Stay Whiskey Creek Area

Tropical Mango Grove Stay Whiskey Creek Area
2.0 star property
McGregor
The price is CA $143
CA $409 total
includes taxes & fees
Aug 5 - Aug 6
Tropical Mango Grove Stay Whiskey Creek Area

16. Hibiscus House Bed Breakfast Citrus Room

Hibiscus House Bed Breakfast Citrus Room
2.0 star property
Fort Myers River District
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely beautiful room and amenities and the breakfast was delicious and with so many options. Loved the communication and cannot wait to come back! "
United States
Crissa
The price is CA $206
CA $310 total
includes taxes & fees
Aug 25 - Aug 26
Hibiscus House Bed Breakfast Citrus Room

17. Hibiscus House Bed Breakfast Inn Parrot Room

Hibiscus House Bed Breakfast Inn Parrot Room
2.0 star property
Fort Myers River District
10.0 out of 10, Exceptional, (2 reviews)
"Easy check in, clean room and very close to many restaurants and bars"
United States
david
The price is CA $209
CA $313 total
includes taxes & fees
Aug 3 - Aug 4
Hibiscus House Bed Breakfast Inn Parrot Room

18. Hibiscus House Bed Breakfast Seashell Room

Hibiscus House Bed Breakfast Seashell Room
2.0 star property
Fort Myers River District
The price is CA $209
CA $313 total
includes taxes & fees
Aug 4 - Aug 5
Hibiscus House Bed Breakfast Seashell Room

19. Riverfront Home w Private Dock Pool Beaches

Riverfront Home w Private Dock Pool Beaches
2.0 star property
McGregor
The price is CA $365
CA $1,199 total
includes taxes & fees
Aug 4 - Aug 5
Riverfront Home w Private Dock Pool Beaches
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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Top Pineland Hotel Reviews

Find out more about Pineland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Pineland. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **: This vacation home rental outside of Pineland is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Pineland?

Expedia has 10 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.