A waterfront with palm trees and a boat dock.

Pineland Vacation Rentals

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Our top choices for Pineland vacation rentals

3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
Bokeelia
10.0 out of 10, Exceptional, (8 reviews)
"The home was absolutely perfect , clean, spacious, and very comfortable. Beautifully decorated , beds were cozy, and everything was exactly as described. The host was friendly and responsive, which made the stay stress-free. Great location and a perfect home base for our family trip.”"
United States
Kelly R.
$385 nightly
The price is $425
Aug 2 - Aug 3
Total with taxes and fees
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (292 reviews)
"Very nice alternative to a motel quite clean everything you need for your stay. highly recommend this property"
United States
PETER
$186 nightly
The price is $199
Jul 25 - Jul 26
Total with taxes and fees
Matlacha Tiny Village

Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
Bokeelia
9.8 out of 10, Exceptional, (18 reviews)
"peaceful and quiet in a great place to getaway"
United States
Louis
$282 nightly
The price is $311
Jul 25 - Jul 26
Total with taxes and fees
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (50 reviews)
"We had a great stay, was exactly as described. The host had great communication and gave great advice for the property and surrounding area."
United States
Jennifer D.
$334 nightly
The price is $368
Aug 11 - Aug 12
Total with taxes and fees
NEW!! The “WATERSIDE” COTTAGE~With dockage

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, (1,272 reviews)
"Really cute and calm beautiful place to stay."
United States
Maria
$206 nightly
The price is $231
Aug 2 - Aug 3
Total with taxes and fees
The Suites at Fishermen’s Village- 2 Bedroom Suites

50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.
Matlacha
10.0 out of 10, Exceptional, (40 reviews)
"Dana was easy to get ahold of and very helpful. The house was roomy and inviting and well appointed. Very nice stay"
United States
Jeanne/James B.
$404 nightly
The price is $446
Jul 25 - Jul 26
Total with taxes and fees
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

Tiny home glamping unit in pine island on a 6 acre property

Tiny home glamping unit in pine island on a 6 acre property
Saint James City
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful setting, terrific host, just right for our one night stay!"
United States
A P.
$129 nightly
The price is $142
Aug 3 - Aug 4
Total with taxes and fees
Tiny home glamping unit in pine island on a 6 acre property

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, (9 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.
$160 nightly
The price is $176
Jul 25 - Jul 26
Total with taxes and fees
Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,825 reviews)
"I love this place, my favorite place to vacations."
United States
Johanna
$219 nightly
The price is $245
Jul 26 - Jul 27
Total with taxes and fees
Edison Beach House

Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,139 reviews)
"The place was amazing and the host was very gracious."
United States
Wendy
$259 nightly
The price is $289
Aug 4 - Aug 5
Total with taxes and fees
Island Inn

Car-Free Island Escape | Pool, Spa + Golf Cart

Car-Free Island Escape | Pool, Spa + Golf Cart
North Captiva
10.0 out of 10, Exceptional, (12 reviews)
"We had an excellent stay. "
United States
Ana A.
$1,322 nightly
The price is $1,455
Jul 26 - Jul 27
Total with taxes and fees
Car-Free Island Escape | Pool, Spa + Golf Cart

Sunny By You Beach House: North Captiva, Private Pool, Steps to Beach, Golf Cart

Sunny By You Beach House: North Captiva, Private Pool, Steps to Beach, Golf Cart
North Captiva
10.0 out of 10, Exceptional, (30 reviews)
"Great place"
United States
Rich M.
$1,222 nightly
The price is $1,345
Jul 27 - Jul 28
Total with taxes and fees
Sunny By You Beach House: North Captiva, Private Pool, Steps to Beach, Golf Cart

Ultra Modern Home w Heated Salt water Pool pet friendly

Ultra Modern Home w Heated Salt water Pool pet friendly
Mariner
10.0 out of 10, Exceptional, (17 reviews)
"Host communication was great. Location was great, would recommend! "
United States
Tori H.
$429 nightly
The price is $473
Jul 26 - Jul 27
Total with taxes and fees
Ultra Modern Home w Heated Salt water Pool pet friendly

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,670 reviews)
"Excellent stay and amenities for families. "
United States
Megan
$435 nightly
The price is $485
Aug 17 - Aug 18
Total with taxes and fees
Sundial Beach Resort & Spa

Gorgeous Bayview Residence on Captiva Island

Gorgeous Bayview Residence on Captiva Island
Captiva
9.6 out of 10, Exceptional, (23 reviews)
"Well kept condo."
United States
Joseph S.
$571 nightly
The price is $629
Jul 25 - Jul 26
Total with taxes and fees
Gorgeous Bayview Residence on Captiva Island

Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (294 reviews)
"Clean room, good location, easy check in instructions."
United States
Brooklyn
$87 nightly
The price is $97
Aug 6 - Aug 7
Total with taxes and fees
Lazy Cuckoo Inn

The Chic Shack: Elevated Beachfront Luxury & Designer Views at Beach Villa 2414

The Chic Shack: Elevated Beachfront Luxury & Designer Views at Beach Villa 2414
Captiva
9.4 out of 10, Exceptional, (31 reviews)
"The place was very nice ."
United States
Cathy S.
$561 nightly
The price is $618
Jul 26 - Jul 27
Total with taxes and fees
The Chic Shack: Elevated Beachfront Luxury & Designer Views at Beach Villa 2414

4BR Captiva Home with Private Pool & Steps to the Beach

4BR Captiva Home with Private Pool & Steps to the Beach
Captiva
9.8 out of 10, Exceptional, (47 reviews)
"Great stay, close to beach, good beach amenities, comfortable home."
United States
Dana P.
$1,148 nightly
The price is $1,264
Jul 26 - Jul 27
Total with taxes and fees
4BR Captiva Home with Private Pool & Steps to the Beach

Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift

Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift
St James City
9.6 out of 10, Exceptional, (94 reviews)
"This home was great for my family we will try to rent again!!!!All-around great home and short vacation?????"
United States
Clint F.
$444 nightly
The price is $489
Jul 26 - Jul 27
Total with taxes and fees
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift

Stunning Harborview Residence on Captiva Island

Stunning Harborview Residence on Captiva Island
Captiva
9.2 out of 10, Wonderful, (31 reviews)
"Very nice condo overlooking waterway. Nice pool and easy in and out. "
United States
William B.
$479 nightly
The price is $528
Jul 25 - Jul 26
Total with taxes and fees
Stunning Harborview Residence on Captiva Island
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 $97 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 10 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 Sanibel Island Southern Beach.

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.