Photo by Suzanne McCoy

Pineland Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Pineland

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (991)
"Clean room great staff "
The price is NZ$327
includes taxes & fees
30 Sept - 1 Oct
The Suites at Fishermen’s Village- 2 Bedroom Suites

Edison Beach House

3.5 star property
9.4 out of 10, Exceptional, (1507)
"Right on the beach and there are several shops and restaurants/bars with in close walking distance! "
Edison Beach House

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

9.6 out of 10, Exceptional, (98)
"Everything was perfect."
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

Sundial Beach Resort & Spa

5.0 star property
8.6 out of 10, Excellent, (2578)
"The ocean view 1 minute to the beach"
The price is NZ$834
includes taxes & fees
6 Oct - 7 Oct
Sundial Beach Resort & Spa

Island Inn

3.5 star property
9.4 out of 10, Exceptional, (1109)
"A great place to enjoy the beach. Beautiful sunsets, We will definitely be back to Island Inn. Thanks for a great vacation!!!"
The price is NZ$423
includes taxes & fees
30 Sept - 1 Oct
Island Inn

Landing Apartments near North Fort Myers

4.0 star property
9.4 out of 10, Exceptional, (40)
"Overall a great experience."
Landing Apartments near North Fort Myers

Matlacha Tiny Village

3.0 star property
8.8 out of 10, Excellent, (265)
"Very nice place with all necesary accommodations for a Pleasant stay. "
The price is NZ$354
includes taxes & fees
30 Sept - 1 Oct
Matlacha Tiny Village

Lazy Cuckoo Inn

2.0 star property
9.0 out of 10, Wonderful, (216)
"Perfect place to stay"
The price is NZ$235
includes taxes & fees
30 Sept - 1 Oct
Lazy Cuckoo Inn

Heated Pool Home on a Canal

9.8 out of 10, Exceptional, (63)
"The property was beautiful and everything was perfect. 10/10 recommend! "
Heated Pool Home on a Canal

- Southern exposure- gulf access- Canal - heated Pool

4.0 star property
9.4 out of 10, Exceptional, (74)
"We brought our family here for a week for spring break and had a wonderful stay - would recommend for other families! "
- Southern exposure- gulf access- Canal - heated Pool

Landing Fort Myers Forestwood

4.0 star property
Landing Fort Myers Forestwood

Gorgeous Sunset Views, Right on the Beach! Community Pool & Over $150 of Free Daily Activities!

9.2 out of 10, Wonderful, (66)
"Clean, great area and views, communication great and very prompt in responding. "
Gorgeous Sunset Views, Right on the Beach! Community Pool & Over $150 of Free Daily Activities!

Western Exposure on cul-de-sac with spill over spa pool & boat dock. SUNSETS!

10.0 out of 10, Exceptional, (57)
"We had a wonderful time. The pool was great. We will definitely be back soon."
Western Exposure on cul-de-sac with spill over spa pool & boat dock. SUNSETS!

HOT SALE Beautiful Villa Lake View Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!

10.0 out of 10, Exceptional, (209)
"Was a perfect stay. Would recommend it to everyone"
HOT SALE Beautiful Villa Lake View Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!

Beach Bungalow 2B/2B Private Pool/Spa, North End, Newly Renovated

9.8 out of 10, Exceptional, (109)
"great location. super nice."
The price is NZ$892
includes taxes & fees
30 Sept - 1 Oct
Beach Bungalow 2B/2B Private Pool/Spa, North End, Newly Renovated

Villa Margarita - 4 Bedroom w/ Beautiful Lake View and Gulf Access!

10.0 out of 10, Exceptional, (26)
"The house was great and the location, especially walking distance to a nice park was a huge plus."
Villa Margarita - 4 Bedroom w/ Beautiful Lake View and Gulf Access!

Resort Harbour Properties

3.5 star property
9.6 out of 10, Exceptional, (359)
"10/10 would stay there again"
Resort Harbour Properties

BEAUTIFUL SANIBEL ISLAND CONDO!!! - NEW EVERYTHING -NEW AMENITIES!!!

4.0 star property
9.8 out of 10, Exceptional, (49)
"Property was well maintained. Close to beach. Lovely area."
BEAUTIFUL SANIBEL ISLAND CONDO!!! - NEW EVERYTHING -NEW AMENITIES!!!

“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING

10.0 out of 10, Exceptional, (5)
"We had been looking forward to our family vacation for quite awhile with excitement and the home did not disappoint! Clean, light and bright with a stunning view. We will definitely be back!"
“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING

Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

9.2 out of 10, Wonderful, (19)
"We took our multigenerational family for a few days of quiet & sunshine. They loved the place so mush that they want to go back next year!We had a few problems with the house but the management team made it right.Lovely place to spend a few days - or more!"
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts
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

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$235 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 15 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.