Photo by Rick Tuers

Pineland Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Our top choices for Pineland holiday rentals

Summerwinds Ct Cul De Sac Bside Duplex a few miles from Ft Myers Beach & Sanibel

Summerwinds Ct Cul De Sac Bside Duplex a few miles from Ft Myers Beach & Sanibel
Iona
9.4 out of 10, Exceptional, (26)
"Perfect spot for all shopping and short drive to the beach! "
United States
Maria S.
The price is NZ$507
includes taxes & fees
31 Dec - 1 Jan 2026
Summerwinds Ct Cul De Sac Bside Duplex a few miles from Ft Myers Beach & Sanibel

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, (1063)
"Beautiful room. Wonderful staff & views."
United States
Christina
The price is NZ$389
includes taxes & fees
4 Jan - 5 Jan 2026
The Suites at Fishermen’s Village- 2 Bedroom Suites

Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
9.0 out of 10, Wonderful, (226)
"Room was very clean, and spacious. Very convenient location for Ft. Myers’s beach and Sanibel. "
United States
ANNA
The price is NZ$218
includes taxes & fees
1 Jan - 2 Jan 2026
Lazy Cuckoo Inn

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, (1)
"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 NZ$381
includes taxes & fees
6 Jan - 7 Jan 2026
Hibiscus House Bed Breakfast Citrus Room

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (269)
"Super clean! Super cute and easy for two. It is close to the road so we hear traffic, but the white noise helped with that. Communication was flawless! Would stay again. "
United States
Rhonda
The price is NZ$354
includes taxes & fees
11 Jan - 12 Jan 2026
Matlacha Tiny Village

New Fully Renovated Condo Unit 2A

New Fully Renovated Condo Unit 2A
Punta Gorda Isles
10.0 out of 10, Exceptional, (14)
"The condo was very nice, clean. It was located near everything stores, restaurants and bars.The price was very reasonable and we'll definitely stay here again. "
United States
C. D.
The price is NZ$467
includes taxes & fees
4 Jan - 5 Jan 2026
New Fully Renovated Condo Unit 2A

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2584)
"wonderful family friendly and spotless resort"
United States
Mary Anne
The price is NZ$769
includes taxes & fees
7 Jan - 8 Jan 2026
Sundial Beach Resort & Spa

Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.

Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.
Pelican
9.4 out of 10, Exceptional, (38)
"Everything was as listed! My husband and I had a great stay while visiting friends. Location was perfect and the space was super cozy! Would definitely recommend!"
United States
julie l.
The price is NZ$516
includes taxes & fees
4 Jan - 5 Jan 2026
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.

Waterfront Condo with Pool & Boat Slip

Waterfront Condo with Pool & Boat Slip
Caloosahatchee
9.8 out of 10, Exceptional, (33)
"What a fabulous place!! Was surprised about the homey feel! Neighbors were wonderful and everyone was welcoming!! Can't wait to go back!!"
United States
Sherry V.
The price is NZ$651
includes taxes & fees
10 Jan - 11 Jan 2026
Waterfront Condo with Pool & Boat Slip

Boho getaway - walkable to downtown Fort Myers!

Boho getaway - walkable to downtown Fort Myers!
Fort Myers River District
9.2 out of 10, Wonderful, (30)
"Comfortable place, convenient area"
United States
Don H.
The price is NZ$576
includes taxes & fees
27 Jan - 28 Jan 2026
Boho getaway - walkable to downtown Fort Myers!

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1597)
"Awesome stay "
United States
mary
The price is NZ$405
includes taxes & fees
3 Jan - 4 Jan 2026
Edison Beach House

Canal front new everything near Boca Grande Beach

Canal front new everything near Boca Grande Beach
Oakland Hills
8.4 out of 10, Very good, (6)
"We stayed for one month. Property was very clean, outside finishing up on storm repairs and completed couple days after we arrived. Safe area away from noise, but close drive to beaches and restaurants."
United States
Kristine G.
The price is NZ$536
includes taxes & fees
31 Dec - 1 Jan 2026
Canal front new everything near Boca Grande Beach

Hidden Secret Waterfront Retreat

Hidden Secret Waterfront Retreat
2.0 star property
Hancock
10.0 out of 10, Exceptional, (4)
"The pool was very nice, and the seating by the canal was amazing, it was so relaxing, and the owner was quick to respond and very friendly!"
United States
bethany r.
The price is NZ$620
includes taxes & fees
6 Jan - 7 Jan 2026
Hidden Secret Waterfront Retreat

So Coastal! A family and pet friendly home

So Coastal! A family and pet friendly home
Iona
9.6 out of 10, Exceptional, (5)
"Property was very clean and updated. Nice screened in porch, kitchen and bath. Host was very responsive and check in process was easy. "
United States
Jeffery L.
The price is NZ$337
includes taxes & fees
3 Jan - 4 Jan 2026
So Coastal! A family and pet friendly home

Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!

Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
Pelican
9.6 out of 10, Exceptional, (54)
"Every time excellent in every way!!!"
United States
Kim G.
The price is NZ$541
includes taxes & fees
3 Jan - 4 Jan 2026
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!

Studio#1-Back Bay Sunsets in Matlacha

Studio#1-Back Bay Sunsets in Matlacha
Matlacha
9.0 out of 10, Wonderful, (11)
"The location and the property were both ideal for our getaway. "
United States
Trent
The price is NZ$369
includes taxes & fees
19 Jan - 20 Jan 2026
Studio#1-Back Bay Sunsets in Matlacha

Historic Fort Myers home

Historic Fort Myers home
Altamont Manor
9.2 out of 10, Wonderful, (32)
"Great place, perfect area."
United States
Renier H.
The price is NZ$592
includes taxes & fees
12 Jan - 13 Jan 2026
Historic Fort Myers home

2 Person Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

2 Person Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
Matlacha
9.8 out of 10, Exceptional, (8)
"This is a wonderful property with a fantastic manager -Stacey. It is beautiful with great amenities and a great location."
United States
David H.
The price is NZ$292
includes taxes & fees
4 Jan - 5 Jan 2026
2 Person Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown

Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown
Caloosahatchee
9.2 out of 10, Wonderful, (31)
"Loved our stay! The beds were clean and soft. The laundry machines were so convenient and that balcony was super relaxing and easy to enjoy. The bathrooms were fully equipped and very nice! I loved the Kcup coffee machine and the kitchen island, plus their lighting! Super close to grocery, beaches, and Water Park! "
United States
Christine
The price is NZ$497
includes taxes & fees
10 Jan - 11 Jan 2026
Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown

The Luxury spot 2 min to DOWNTOWN/ 5 min to the beach

The Luxury spot 2 min to DOWNTOWN/ 5 min to the beach
2.0 star property
Fort Myers River District
10.0 out of 10, Exceptional, (2)
"The apartment was very clean. We had an excellent stay. We will definitely stay again."
United States
Matt P.
The price is NZ$373
includes taxes & fees
9 Jan - 10 Jan 2026
The Luxury spot 2 min to DOWNTOWN/ 5 min to the beach
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pineland Hotel Reviews

Find out more about Pineland

Everything you need to know about Pineland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pineland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pineland holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pineland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pineland holiday rentals we have selected for you start as low as NZ$218 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pineland rentals

At Expedia, we put the best Pineland holiday 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 holiday.

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 holiday rentals in Pineland?

Yes, there are holiday rentals close to the most popular sights in Pineland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pineland has to offer?

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

How many holiday rentals are there in Pineland?

Expedia has 8 holiday 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 wider area, you’ll find Randell Research Center and Useppa Island.

What are holiday rentals like in Pineland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pineland. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for families.