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Pineland Holiday Rentals

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Holiday Rentals in Pineland

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (1009)
"Fantastic place to stay! Everything was top notch! "
United States
Julie
The price is AU$287
includes taxes & fees
30 Oct - 31 Oct
The Suites at Fishermen’s Village- 2 Bedroom Suites
Edison Beach House
3.5 star property
9.4 out of 10, Exceptional, (1539)
"All around great place to stay"
United States
David
The price is AU$315
includes taxes & fees
26 Oct - 27 Oct
Edison Beach House
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **
9.6 out of 10, Exceptional, (100)
"Everything was perfect."
United States
Tom C.
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **
Sundial Beach Resort & Spa
5.0 star property
8.6 out of 10, Excellent, (2579)
"Thank you for a great stay!"
United States
Jessica
The price is AU$652
includes taxes & fees
26 Oct - 27 Oct
Sundial Beach Resort & Spa
Landing Apartments near North Fort Myers
4.0 star property
9.4 out of 10, Exceptional, (41)
"Great place to stay."
Costa Rica
Anonymous traveller
Landing Apartments near North Fort Myers
Island Inn
3.5 star property
9.4 out of 10, Exceptional, (1111)
"A great place to enjoy the beach. Beautiful sunsets, We will definitely be back to Island Inn. Thanks for a great vacation!!!"
United States
Dave
The price is AU$375
includes taxes & fees
26 Oct - 27 Oct
Island Inn
Lazy Cuckoo Inn
2.0 star property
9.0 out of 10, Wonderful, (216)
"Perfect place to stay"
United States
Nancy
The price is AU$143
includes taxes & fees
28 Oct - 29 Oct
Lazy Cuckoo Inn
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. "
United States
isabel
The price is AU$278
includes taxes & fees
9 Nov - 10 Nov
Matlacha Tiny Village
Landing Fort Myers Forestwood
4.0 star property
2.0 out of 10, (1)
Landing Fort Myers Forestwood
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts
9.2 out of 10, Wonderful, (19)
"Wonderful stay with a large family of 16. Dreamcatcher is a beautifully decorated home that had everything we needed! From the gorgeous views, comfortable beds, nice showers, and fully stocked kitchen it is truly a slice of paradise! There were two golf carts to explore the island but also a short walk to the beach where we watched the most beautiful sunsets. Would highly recommend and hope to stay at Dreamcatcher again! "
United States
Beth H.
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts
Heated Pool Home on a Canal
9.8 out of 10, Exceptional, (64)
"The property was beautiful and everything was perfect. 10/10 recommend! "
United States
Shana G.
Heated Pool Home on a Canal
“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!"
United States
Nathan M.
“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING
Big on the Beach House 6BR Home + Club Access, Private Dock & Stunning Views
9.8 out of 10, Exceptional, (72)
"Great trip!"
United States
Patricia D.
Big on the Beach House 6BR Home + Club Access, Private Dock & Stunning Views
South Seas Bayside Villa 5130: Your Perfect Island Retreat
8.4 out of 10, Very good, (18)
"Beautiful apartment "
United States
Michael
South Seas Bayside Villa 5130: Your Perfect Island Retreat
Spacious 4 BR, 3BA in Popular Yacht Club, Heated Salt Pool. Sail Boat Access!
9.8 out of 10, Exceptional, (83)
"Very nice clean and neat."
United States
Eddie J.
Spacious 4 BR, 3BA in Popular Yacht Club, Heated Salt Pool. Sail Boat Access!
5 bedroom, South facing, FREE heated salt water pool, with Direct Gulf access
9.6 out of 10, Exceptional, (121)
"Beautiful and clean. Very responsive and go above and beyond to ensure your stay is great. Highly recommend if staying in the area."
United States
Makenna P.
5 bedroom, South facing, FREE heated salt water pool, with Direct Gulf access
Beautiful Villa Lake View Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!
10.0 out of 10, Exceptional, (211)
"This was our second trip and just like the first time it was wonderful. Other than maybe to go get groceries or out to dinner a time or two this location has everything we needed to just stay in and enjoy a nice week away."
United States
Caitlyn H.
Beautiful Villa Lake View Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!
BEAUTY AND THE BEACH- BEACHFRONT MANSION, HEATED POOL
10.0 out of 10, Exceptional, (11)
"I don't think there is a better property on the island. The pool is very private. You are a short walk from the beach, and the sunsets are breathtaking. This property has it all!"
United States
Phillip H.
BEAUTY AND THE BEACH- BEACHFRONT MANSION, HEATED POOL
Steps to BEACH/POOL/Times square
9.8 out of 10, Exceptional, (11)
"We really enjoy staying at this property. It was very clean, comfortable, and with everything you need to enjoy your stay, complete kitchen, bathroom with shampoo and conditioner, beach towels. Very well located, walking distance to beach and downtown/restaurants. I would stay here again."
United States
Rina
Steps to BEACH/POOL/Times square
Your Finest Vacation!
9.8 out of 10, Exceptional, (138)
"Spending a few days at the Majestic Villa was a wonderful experience which I would do immediately again. A wonderful place to relax with family/friends. The villa is in good shape, clean with all available which you need to spend a good time. "
United States
Juerg N.
Your Finest Vacation!
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

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 favourite 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 depend 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 AU$143 per night. Entering your travel dates in the search wizard might find you 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 16 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.