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Pineland Vacation Rentals

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Our top choices for Pineland vacation rentals

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, (1,072 reviews)
"Excellent location and comfortable. Spacious rooms with full kitchens. "
United States
Janet
$250 nightly
The price is $280
Feb 1 - Feb 2
Total with taxes and fees
The Suites at Fishermen’s Village- 2 Bedroom Suites

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (272 reviews)
"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
$193 nightly
The price is $207
Jan 12 - Jan 13
Total with taxes and fees
Matlacha Tiny Village

Cute Studio in Cape Coral

Cute Studio in Cape Coral
Hancock
9.8 out of 10, Exceptional, (11 reviews)
"Had a great time everything was perfect"
Canada
Michael H.
$202 nightly
The price is $223
Jan 13 - Jan 14
Total with taxes and fees
Cute Studio in Cape Coral

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 reviews)
"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.
$255 nightly
The price is $280
Jan 12 - Jan 13
Total with taxes and fees
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.

Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
9.0 out of 10, Wonderful, (233 reviews)
"Very nice. Great for a short or longer term stay."
United States
Finley
$107 nightly
The price is $120
Jan 13 - Jan 14
Total with taxes and fees
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 review)
"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
$203 nightly
The price is $226
Jan 15 - Jan 16
Total with taxes and fees
Hibiscus House Bed Breakfast Citrus Room

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

Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
Matlacha
9.8 out of 10, Exceptional, (8 reviews)
"This is a wonderful property with a fantastic manager -Stacey. It is beautiful with great amenities and a great location."
United States
David H.
$135 nightly
The price is $148
Jan 12 - Jan 13
Total with taxes and fees
Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

Hidden Secret Waterfront Retreat

Hidden Secret Waterfront Retreat
2.0 star property
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"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.
$334 nightly
The price is $367
Jan 12 - Jan 13
Total with taxes and fees
Hidden Secret Waterfront Retreat

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Oakland Hills
9.8 out of 10, Exceptional, (61 reviews)
"We had a great time even the weather was bad we had an amazing time in the home play games and watch movies "
United States
Adam L.
$284 nightly
The price is $314
Jan 12 - Jan 13
Total with taxes and fees
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

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 reviews)
"The apartment was very clean. We had an excellent stay. We will definitely stay again."
United States
Matt P.
$194 nightly
The price is $213
Jan 19 - Jan 20
Total with taxes and fees
The Luxury spot 2 min to DOWNTOWN/ 5 min to the beach

HEATED POOL-LANAI-BBQ-5 Mi to BEACH-WASHER/DRYER-TENNIS-GOLF-BLISSFUL RETREAT

HEATED POOL-LANAI-BBQ-5 Mi to BEACH-WASHER/DRYER-TENNIS-GOLF-BLISSFUL RETREAT
Rotonda Heights
9.8 out of 10, Exceptional, (7 reviews)
"Close to what we wanted to do for our fishing trip."
United States
Edward S.
$336 nightly
The price is $371
Jan 16 - Jan 17
Total with taxes and fees
HEATED POOL-LANAI-BBQ-5 Mi to BEACH-WASHER/DRYER-TENNIS-GOLF-BLISSFUL RETREAT

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 reviews)
"Perfect spot for all shopping and short drive to the beach! "
United States
Maria S.
$269 nightly
The price is $296
Feb 7 - Feb 8
Total with taxes and fees
Summerwinds Ct Cul De Sac Bside Duplex a few miles from Ft Myers Beach & Sanibel

Gulf Access Condo Heated Pool & Dock

Gulf Access Condo Heated Pool & Dock
Caloosahatchee
10.0 out of 10, Exceptional, (26 reviews)
"The property was very clean and well equipped. Beautiful location on the canal."
United States
Kathleen
$325 nightly
The price is $356
Jan 12 - Jan 13
Total with taxes and fees
Gulf Access Condo Heated Pool & Dock

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Oakland Hills
9.8 out of 10, Exceptional, (15 reviews)
"It was beautiful especially Boca Grande, went on a charter fish trip which was amazing. The property was also amazing nice dock and canoed the first day it was fun but then we saw a lot of gators but overall would come again! "
United States
Caleb R.
$286 nightly
The price is $316
Jan 16 - Jan 17
Total with taxes and fees
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,611 reviews)
"Location, staff, room with view…all were excellent. Will stay again!"
United States
Leah
$225 nightly
The price is $251
Jan 12 - Jan 13
Total with taxes and fees
Edison Beach House

The perfect blend of comfort and convenience in our cozy studio apartment

The perfect blend of comfort and convenience in our cozy studio apartment
Jacarandas
10.0 out of 10, Exceptional, (7 reviews)
"Great place to stay I would highly recommend to anyone looking for a nice clean place to stay."
United States
Ward
$168 nightly
The price is $185
Jan 31 - Feb 1
Total with taxes and fees
The perfect blend of comfort and convenience in our cozy studio apartment

Beautiful house with canal view…

Beautiful house with canal view…
Pebble Beach
9.0 out of 10, Wonderful, (32 reviews)
"Property was exactly as described and was extremely clean and had anything you could possibly need. Close to everything and bed was comfortable check / out was easy"
United States
John K.
Beautiful house with canal view…

Studio#1-Back Bay Sunsets in Matlacha

Studio#1-Back Bay Sunsets in Matlacha
Matlacha
9.0 out of 10, Wonderful, (11 reviews)
"The location and the property were both ideal for our getaway. "
United States
Trent
$185 nightly
The price is $204
Jan 19 - Jan 20
Total with taxes and fees
Studio#1-Back Bay Sunsets in Matlacha

Location!! Location!!! Gulf Access Villa in SE Area

Location!! Location!!! Gulf Access Villa in SE Area
2.0 star property
Caloosahatchee
8.6 out of 10, Excellent, (14 reviews)
"Very comfortable, nicely decorated. Felt like home."
United States
Sharon P.
$299 nightly
The price is $329
Jan 18 - Jan 19
Total with taxes and fees
Location!! Location!!! Gulf Access Villa in SE Area

So Coastal! A family and pet friendly home

So Coastal! A family and pet friendly home
Iona
9.6 out of 10, Exceptional, (5 reviews)
"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.
$170 nightly
The price is $185
Jan 12 - Jan 13
Total with taxes and fees
So Coastal! A family and pet friendly home
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 $120 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?

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 7 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.