A waterfront with palm trees and a boat dock.

Pineland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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 Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (298 reviews)
"So cute and clean nice dock to sit and relax or fish. Kayaks available to use free as well with life jackets paddles, etc. well equipped rental we can’t wait to go again! Great communication with hosts."
United States
Lori
The price is P8,308
P13,974 total
includes taxes & fees
Oct 26 - Oct 27
Matlacha Tiny Village
A beach with a prominent dead tree trunk, sandy shore, and calm sea.

2. 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 P12,168
P24,837 total
includes taxes & fees
Oct 19 - Oct 20
MALU LANI Inn & Marina
A beach with a view of the ocean and a sunset.

3. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,162 reviews)
"Great location"
United States
Nicole
The price is P15,553
P17,341 total
includes taxes & fees
Oct 17 - Oct 18
Island Inn
A beach with a thatched-roof structure, palm trees, and a view of the sea.

4. The Suites at Fishermen’s Village

The Suites at Fishermen’s Village
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,344 reviews)
"Stay here every time I visit Florida. Highly recommend"
United States
Dawn
The price is P10,766
P12,058 total
includes taxes & fees
Oct 25 - Oct 26
The Suites at Fishermen’s Village
A modern living room with a flat-screen TV, a floor lamp, a dining table, and a sofa.

5. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (301 reviews)
"Great place!"
United States
Bruce
The price is P3,705
P6,162 total
includes taxes & fees
Oct 28 - Oct 29
Lazy Cuckoo Inn
A beach view from a balcony with a pool, palm trees, and a building with a balcony.

6. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,940 reviews)
"Great stay."
United States
Angie
The price is P11,319
P15,075 total
includes taxes & fees
Oct 18 - Oct 19
Edison Beach House
A pool area with lounge chairs and umbrellas, a beach with umbrellas and lounge chairs, and palm trees.

7. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,715 reviews)
"Love the resort and great access to beach"
United States
Lisa Renee
The price is P22,468
P29,189 total
includes taxes & fees
Oct 18 - Oct 19
Sundial Beach Resort & Spa
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

Driftwood Inn
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (11 reviews)
"This was our second stay at Driftwood Inn and we enjoyed it as much this time as the last! Property is immaculately cleaned, comfortable and has everything we need. The beach is a short walk away and the included cart, umbrellas and beach chairs make it easy to enjoy your time relaxing in the sun. Highly recommend this property for your beach time!"
United States
Heather
The price is P13,565
P30,294 total
includes taxes & fees
Oct 28 - Oct 29
Driftwood Inn
A bedroom with a bed, a nightstand, a lamp, and a window with blinds.

9. Lakeside Oasis Fort Myers

Lakeside Oasis Fort Myers
2.0 star property
Iona
The price is P7,299
P15,841 total
includes taxes & fees
Oct 28 - Oct 29
Lakeside Oasis Fort Myers
A balcony with wicker chairs and a glass table, overlooking a colorful building with a metal roof.

10. Harbour House at the Inn 308

Harbour House at the Inn 308
3.0 star property
Fort Myers Beach
The price is P25,120
P36,172 total
includes taxes & fees
Oct 28 - Oct 29
Harbour House at the Inn 308
A living room with a sectional sofa, a rug, a framed picture, and a door leading to another room.

11. 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 P6,092
P21,354 total
includes taxes & fees
Oct 28 - Oct 29
Fort Myers Escape Near Downtown & Beach w/ Parking
A modern kitchen with white cabinets, a dining area with a wooden table and chairs, and a view of a pool through a glass door.

12. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
Oakland Hills
The price is P8,578
P25,835 total
includes taxes & fees
Oct 18 - Oct 19
Dreams Away - Sleeps 10 Pool Golf Fun
A living room with a ceiling fan, a sofa with nautical-themed pillows, a coffee table, and a rug with a starfish design.

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

3 Mi to Fort Myers Beach! Family Getaway w/ Pool
3.0 star property
Iona
The price is P9,420
P27,634 total
includes taxes & fees
Nov 4 - Nov 5
3 Mi to Fort Myers Beach! Family Getaway w/ Pool
A modern kitchen with white cabinetry, a central island, and stainless steel appliances.

14. Riverfront Home w Private Dock Pool Beaches

Riverfront Home w Private Dock Pool Beaches
2.0 star property
McGregor
The price is P16,354
P57,253 total
includes taxes & fees
Oct 19 - Oct 20
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pineland Hotel Reviews

Edison Beach House

Edison Beach House

10/10 Excellent
"Loved everything"
Patricia 2-night trip
Posted 1 hour ago
Edison Beach House

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
  • Use the map to find apartments and other holiday homes in the Pineland neighbourhood you prefer
  • 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.

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.