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Pineland Vacation Rentals

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Vacation Rentals in Pineland

Our top choices for Pineland vacation rentals

Edison Beach House

3.5 star property
9.4 out of 10, Exceptional, (1495)
"Right on the beach and there are several shops and restaurants/bars with in close walking distance! "
The price is CA $210
CA $235 total
includes taxes & fees
Sep 14 - Sep 15
Edison Beach House

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (983)
"Great stay and well managed. Also, very clean and comfortable rooms. "
The price is CA $219
CA $245 total
includes taxes & fees
Sep 26 - Sep 27
The Suites at Fishermen’s Village- 2 Bedroom Suites

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

9.6 out of 10, Exceptional, (97)
"Amazing location with close to the fishing grounds and beautiful views."
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

Sundial Beach Resort & Spa

5.0 star property
8.6 out of 10, Excellent, (2576)
"Very nice Resort. Not a 5 star but they are remodeling. Easy access to the beautiful beach. Resturants were very good. Service was excellent. We went off season so there was not may people on the property which we liked."
The price is CA $430
CA $662 total
includes taxes & fees
Sep 14 - Sep 15
Sundial Beach Resort & Spa

Island Inn

3.5 star property
9.4 out of 10, Exceptional, (1102)
"Nice place peaceful "
The price is CA $359
CA $400 total
includes taxes & fees
Sep 11 - Sep 12
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 CA $136
CA $255 total
includes taxes & fees
Sep 11 - Sep 12
Matlacha Tiny Village

Lazy Cuckoo Inn

2.0 star property
9.0 out of 10, Wonderful, (215)
"Perfect place to stay"
The price is CA $129
CA $189 total
includes taxes & fees
Sep 12 - Sep 13
Lazy Cuckoo Inn

PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

10.0 out of 10, Exceptional, (42)
"We had a wonderful time!"
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

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

10.0 out of 10, Exceptional, (5)
"This property is amazing! Beautiful views and great fishing right off the dock. My wife and I stayed for our belated anniversary and we couldnt have been happier. We will be back."
“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING

Landing Fort Myers Forestwood

4.0 star property
Landing Fort Myers Forestwood

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."
Steps to BEACH/POOL/Times square

Beach View + 1-2 Min walk to Beach + Huge TVs & Fully Remodeled

10.0 out of 10, Exceptional, (8)
Beach View + 1-2 Min walk to Beach + Huge TVs & Fully Remodeled

Resort Harbour Properties

3.5 star property
9.6 out of 10, Exceptional, (357)
"10/10 would stay there again"
Resort Harbour Properties

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

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

4.0 star property
9.8 out of 10, Exceptional, (48)
"Property was well maintained. Close to beach. Lovely area."
BEAUTIFUL SANIBEL ISLAND CONDO!!! - NEW EVERYTHING -NEW AMENITIES!!!

South Seas Bayside Villa 4222

10.0 out of 10, Exceptional, (1)
"It was a wonderful getaway before school starts!"
South Seas Bayside Villa 4222

South Seas Bayside Villa 5130: Your Perfect Island Retreat

8.8 out of 10, Excellent, (16)
"Beautiful apartment "
South Seas Bayside Villa 5130: Your Perfect Island Retreat

Lakefront Luxury Paradise: 80ft Waterfront, Private Pier & Heated Pool Oasis!

10.0 out of 10, Exceptional, (231)
"The house was beautiful, clean, and had everything we needed and then some. Enjoyed the pool ever day and the spa, as well as the wildlife! "
Lakefront Luxury Paradise: 80ft Waterfront, Private Pier & Heated Pool Oasis!

Stunning 3-bedroom condo with high ceilings, beach access and pool!

9.4 out of 10, Exceptional, (3)
"Great property, very well maintained. So many extras that will amaze future guests!"
Stunning 3-bedroom condo with high ceilings, beach access and pool!
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

Find out more about Pineland

Everything you need to know about Pineland vacation rentals

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

Pineland vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pineland vacation rentals we have selected for you start as low as CA $129 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 vacation 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 vacation.

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 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 14 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.