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Pineland Vacation Rentals

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Our top choices for Pineland vacation rentals

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
$393 nightly
The price is $439
Dec 12 - Dec 13
Total with taxes and fees
Sundial Beach Resort & Spa

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, (1043)
"Clean room, beautiful area, excellent staff"
United States
Crystal
$192 nightly
The price is $215
Dec 14 - Dec 15
Total with taxes and fees
The Suites at Fishermen’s Village- 2 Bedroom Suites

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1578)
"Awesome stay "
United States
mary
$237 nightly
The price is $264
Dec 15 - Dec 16
Total with taxes and fees
Edison Beach House

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

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **
North Captiva
9.6 out of 10, Exceptional, (102)
"Absolutely breathtaking! I couldn’t get enough of the views. Sunrises were beautiful and to watch the storms rolling across the water was definitely a sight to see! The house had everything you needed and was super relaxing! We will definitely be back! The host was also super responsive which makes this home even better! Thank you for a wonderful week! "
United States
Kathleen S.
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
9.0 out of 10, Wonderful, (223)
"Great location and very clean, cute place"
United States
Sarah
$84 nightly
The price is $94
Dec 18 - Dec 19
Total with taxes and fees
Lazy Cuckoo Inn

Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1121)
"Really nice, updated, and clean room with a screened waterfront balcony in a perfect place on the island (far enough away from the big resorts to be in a quieter area, but close enough to the center area of the island to be convenient). "
United States
Chris
$219 nightly
The price is $244
Dec 14 - Dec 15
Total with taxes and fees
Island Inn

Resort Harbour Properties

Resort Harbour Properties
3.5 star property
Punta Rassa
9.6 out of 10, Exceptional, (363)
"10/10 would stay there again"
United States
Kristie
$583 nightly
The price is $650
Dec 18 - Dec 19
Total with taxes and fees
Resort Harbour Properties

2 Private Cabanas with kitchen and a Private Pool.

2 Private Cabanas with kitchen and a Private Pool.
Pelican
9.4 out of 10, Exceptional, (27)
"Property manager was great. Really enjoyed our stay. Would highly recommend others to stay here. "
United States
David H.
2 Private Cabanas with kitchen and a Private Pool.

Sanibel Siesta on the Beach

Sanibel Siesta on the Beach
2.5 star property
Mid Island
10.0 out of 10, Exceptional, (3)
"Near the beach beautiful views and very quiet"
Mexico
Alberto
Sanibel Siesta on the Beach

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (268)
"Very nice place with all necesary accommodations for a Pleasant stay. "
United States
isabel
$204 nightly
The price is $219
Dec 19 - Dec 20
Total with taxes and fees
Matlacha Tiny Village

NEW EVERYTHING!! 4-bed 3 bath South Facing spill over spa pool. 2 king suites

NEW EVERYTHING!! 4-bed 3 bath South Facing spill over spa pool. 2 king suites
3.0 star property
Pelican
10.0 out of 10, Exceptional, (24)
"The place was perfect. Location, house, pool, all the things. We can’t wait to book again!"
United States
Lori F.
NEW EVERYTHING!! 4-bed 3 bath South Facing spill over spa pool. 2 king suites

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

Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts
North Captiva
9.2 out of 10, Wonderful, (19)
"Everything was awesome "
United States
Marlen M.
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

BEAUTIFUL NEW CONDO 2025 SANIBEL ISLAND!!! SANDY BEACH POOL 🏝️🌅 🏖️

BEAUTIFUL NEW CONDO 2025 SANIBEL ISLAND!!! SANDY BEACH POOL 🏝️🌅 🏖️
4.0 star property
Mid Island
9.8 out of 10, Exceptional, (53)
"Great communication. Easy check in and out. Very clean and quiet condo. About 100 yard walk to beach. Would recommend to anyone to stay there. "
United States
Martin
BEAUTIFUL NEW CONDO 2025 SANIBEL ISLAND!!! SANDY BEACH POOL 🏝️🌅 🏖️

Luxury family friendly WATERFRONT home with a POOL, PLAYGROUND, FIREPIT & BEACH

Luxury family friendly WATERFRONT home with a POOL, PLAYGROUND, FIREPIT & BEACH
Fort Myers
9.6 out of 10, Exceptional, (26)
"Nice place, full of surprises and the back area was nice to use."
United States
Ivan S.
$356 nightly
The price is $393
Dec 17 - Dec 18
Total with taxes and fees
Luxury family friendly WATERFRONT home with a POOL, PLAYGROUND, FIREPIT & BEACH

Paradise Vacation Pool Home Last minute $155

Paradise Vacation Pool Home Last minute $155
Pelican
10.0 out of 10, Exceptional, (7)
"The place was very nice, our hostess was very attentive to any questions or requests. Overall I definitely look forward to my next visit."
United States
John T.
Paradise Vacation Pool Home Last minute $155

BEACHFRONT LUXURY ISLAND HOME PRIVATE SWIM SPA~DOCK FISHING~GOLF CART STUNNING

BEACHFRONT LUXURY ISLAND HOME PRIVATE SWIM SPA~DOCK FISHING~GOLF CART STUNNING
North Captiva
10.0 out of 10, Exceptional, (5)
"We loved the outdoor patio and view! Excellent outdoor furniture! "
United States
dana t.
BEACHFRONT LUXURY ISLAND HOME PRIVATE SWIM SPA~DOCK FISHING~GOLF CART STUNNING

Your Finest Vacation!

Your Finest Vacation!
Caloosahatchee
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!

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

PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!
Trafalgar
10.0 out of 10, Exceptional, (42)
"We came for a week of total relaxation. It was all that. Pool was amazing, kitchen was fully stocked with everything you could need and the entire place was so comfortable. The pool guys came on Thursday- great guys- very friendly and fast in doing their jobs. Close to everything so there’s always something to do but also was a great place to just be. 5 out of 5 stars! Would definitely stay again "
United States
Heidi S.
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

Coconut Cove House on Canal, Salt Water Pool & Boat Dock

Coconut Cove House on Canal, Salt Water Pool & Boat Dock
Pelican
10.0 out of 10, Exceptional, (24)
"we spent a week in cape coral and had a lovely stay! caught fish right off the dock and the boat lift was perfect for our boat! super toddler/baby friendly! "
United States
Taylor F.
Coconut Cove House on Canal, Salt Water Pool & Boat Dock

Luxurious Waterfront Villa with 4 Bedrooms, Private Heated Pool and Hot Tub!

Luxurious Waterfront Villa with 4 Bedrooms, Private Heated Pool and Hot Tub!
Pelican
9.8 out of 10, Exceptional, (125)
"Great place to spent your holiday. We really enjoyed the house, the pool and the neighborhood. A full recommendation and a five star rating. Thank you Damien"
Germany
Björn H.
Luxurious Waterfront Villa with 4 Bedrooms, Private Heated Pool and Hot Tub!
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 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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Pineland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $94 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Luxury family friendly WATERFRONT home with a POOL, PLAYGROUND, FIREPIT & BEACH : This vacation home rental outside of Pineland is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Pineland?

Expedia has 8 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.