A waterfront with palm trees and a boat dock.

Pineland Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Pineland vacation rentals

Private beach nearby, motor boating, fishing

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 ￥32,330
￥64,650 total
includes taxes & fees
Aug 2 - Aug 3
MALU LANI Inn & Marina
Exterior

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 ￥17,568
￥31,558 total
includes taxes & fees
Aug 6 - Aug 7
Matlacha Tiny Village
House (3 Bedrooms) | Interior

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 ￥20,111
￥55,080 total
includes taxes & fees
Aug 2 - Aug 3
Canalfront St James City Home w/ Unique View
Grand Studio Suite, Kitchenette | Desk, laptop workspace, WiFi (free), bed sheets

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 ￥9,134
￥15,345 total
includes taxes & fees
Aug 20 - Aug 21
Lazy Cuckoo Inn
Property amenity

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 ￥38,147
￥42,534 total
includes taxes & fees
Aug 27 - Aug 28
Island Inn
House, 4 Bedrooms | Living area | Smart TV, streaming services

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 ￥24,117
￥94,162 total
includes taxes & fees
Aug 2 - Aug 3
Sleeps 16 Plus Central Cape Coral Family Escape 4 Bedroom Home
Village Beach & Harbor Suite | Balcony view

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, (1,279 reviews)
"Really cute and calm beautiful place to stay."
United States
Maria
The price is ￥27,960
￥31,315 total
includes taxes & fees
Aug 3 - Aug 4
The Suites at Fishermen’s Village- 2 Bedroom Suites
House | 1 bedroom, high-speed internet

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 ￥23,817
￥35,685 total
includes taxes & fees
Aug 1 - Aug 2
Hibiscus House Bed Breakfast Inn Flamingo Suite
Apartment, Multiple Beds, Partial Ocean View | Beach/ocean view

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 ￥27,149
￥36,499 total
includes taxes & fees
Aug 5 - Aug 6
Edison Beach House
Premium Cottage, Lanai, Garden View | Living area | Smart TV

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 ￥32,465
￥74,664 total
includes taxes & fees
Aug 4 - Aug 5
Driftwood Inn
Exterior

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 ￥63,684
￥79,727 total
includes taxes & fees
Aug 1 - Aug 2
Sundial Beach Resort & Spa
House (3 Bedrooms) | Front of property

12. Beach Days & Backyard Nights! Fort Myers Retreat

Beach Days & Backyard Nights! Fort Myers Retreat
3.0 star property
Harlem Heights
The price is ￥12,290
￥51,801 total
includes taxes & fees
Aug 2 - Aug 3
Beach Days & Backyard Nights! Fort Myers Retreat
House, Accessible | 1 bedroom, high-speed internet

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 ￥23,817
￥35,685 total
includes taxes & fees
Aug 3 - Aug 4
Hibiscus House Bed Breakfast Inn Turtle Room Bed-ada
Apartment (2 Bedrooms) | Front of property

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 ￥11,492
￥45,470 total
includes taxes & fees
Aug 3 - Aug 4
Fort Myers Escape Near Downtown & Beach w/ Parking
House | 2 bedrooms, high-speed internet

15. Tropical Mango Grove Stay Whiskey Creek Area

Tropical Mango Grove Stay Whiskey Creek Area
2.0 star property
McGregor
The price is ￥16,287
￥46,563 total
includes taxes & fees
Aug 5 - Aug 6
Tropical Mango Grove Stay Whiskey Creek Area
House | 1 bedroom, high-speed internet

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 ￥23,817
￥35,685 total
includes taxes & fees
Aug 3 - Aug 4
Hibiscus House Bed Breakfast Citrus Room
House | 1 bedroom, high-speed internet

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 ￥23,817
￥35,685 total
includes taxes & fees
Aug 2 - Aug 3
Hibiscus House Bed Breakfast Inn Parrot Room
House | 1 bedroom, high-speed internet

18. Hibiscus House Bed Breakfast Seashell Room

Hibiscus House Bed Breakfast Seashell Room
2.0 star property
Fort Myers River District
The price is ￥23,817
￥35,685 total
includes taxes & fees
Aug 2 - Aug 3
Hibiscus House Bed Breakfast Seashell Room
House, Accessible | 4 bedrooms

19. Riverfront Home w Private Dock Pool Beaches

Riverfront Home w Private Dock Pool Beaches
2.0 star property
McGregor
The price is ￥41,593
￥136,625 total
includes taxes & fees
Aug 2 - Aug 3
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

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

10/10 Excellent
"Proximity to everything. Property grounds and amenities"
Douglas Ray 4-night trip
Posted 1 hour ago
Marriott Sanibel Harbour Resort & Spa

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:

  • View our selection of featured holiday rentals in Pineland
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  • Enter your travel dates to view the best deals on holiday rentals in Pineland while they last

Look no further and take a look at our great range of rental properties in Pineland!

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.