Pineland Vacation Rentals

Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Pineland vacation rentals

Dining

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, (6 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.
$386 nightly
The price is $426
Jun 21 - Jun 22
Total with taxes and fees
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
Private beach nearby, motor boating, fishing

MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Overall, very friendly Gave me advice about the area Told me what live bands were playing that night Very fun definitely will be back"
United States
Kyle
$365 nightly
The price is $398
Jun 22 - Jun 23
Total with taxes and fees
MALU LANI Inn & Marina
Village Beach & Harbor Suite | Balcony view

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, (1,233 reviews)
"Great location clean and specious"
United States
Kathryn
$206 nightly
The price is $231
Jun 21 - Jun 22
Total with taxes and fees
The Suites at Fishermen’s Village- 2 Bedroom Suites
Smart TV

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, (15 reviews)
"Host communication was great. Location was great, would recommend! "
United States
Tori H.
$406 nightly
The price is $447
Jun 22 - Jun 23
Total with taxes and fees
Ultra Modern Home w Heated Salt water Pool pet friendly
Exterior

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,654 reviews)
"Excellent stay and amenities for families. "
United States
Megan
$471 nightly
The price is $525
Jul 18 - Jul 19
Total with taxes and fees
Sundial Beach Resort & Spa
Premium Cottage, Lanai, Garden View | Living area | Smart TV

Driftwood Inn

Driftwood Inn
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (11 reviews)
"The cottage was well stocked with all we needed. It was also immaculate with a lovely garden. The beach was a 5 minute walk."
United States
Maureen
$518 nightly
The price is $578
Jun 24 - Jun 25
Total with taxes and fees
Driftwood Inn
Beach nearby, sun loungers, beach towels

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, (74 reviews)
"Very nice property, close to beaches and shopping. I especially liked that they had pretty much everything you needed for a beach day."
United States
Melissa
$287 nightly
The price is $317
Jun 19 - Jun 20
Total with taxes and fees
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Terrace/patio

Tiki Retreat

Tiki Retreat
Riverbend Country Club
10.0 out of 10, Exceptional, (16 reviews)
"A great place to stay!!! "
United States
shelby S.
$329 nightly
The price is $363
Jun 24 - Jun 25
Total with taxes and fees
Tiki Retreat
Beach nearby

Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
East End
9.6 out of 10, Exceptional, (51 reviews)
"The unit appeared to be recently remodeled….its beautiful! Perfect for a weekend get away! "
United States
Mary Kay M.
$290 nightly
The price is $307
Jun 21 - Jun 22
Total with taxes and fees
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
Shower, towels

Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!

Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
East End
9.2 out of 10, Wonderful, (72 reviews)
"Great little place, really enjoyed having the kitchen and the grill. "
United States
Eric W.
$305 nightly
The price is $323
Jun 23 - Jun 24
Total with taxes and fees
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
Terrace/patio

Gulf Access Condo Heated Pool & Dock

Gulf Access Condo Heated Pool & Dock
Caloosahatchee
10.0 out of 10, Exceptional, (29 reviews)
"We enjoyed our stay. "
United States
Karen B.
$304 nightly
The price is $334
Jun 19 - Jun 20
Total with taxes and fees
Gulf Access Condo Heated Pool & Dock
Dining

Burnt Store Isles Golf Home, W/Hot Tub/King Bed/Fast WIFI/Unbeatable Location

Burnt Store Isles Golf Home, W/Hot Tub/King Bed/Fast WIFI/Unbeatable Location
Burnt Store Isles
10.0 out of 10, Exceptional, (22 reviews)
"House is always clean. Great location and very quiet neighborhood. "
United States
Yvonne T.
$320 nightly
The price is $354
Jun 22 - Jun 23
Total with taxes and fees
Burnt Store Isles Golf Home, W/Hot Tub/King Bed/Fast WIFI/Unbeatable Location
Exterior

1BR - Short walk to the beach - Colony Inn 46

1BR - Short walk to the beach - Colony Inn 46
East End
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful place to stay. Just minutes to walk to beach and everything was as discribed "
United States
Lisa
$329 nightly
The price is $347
Jul 13 - Jul 14
Total with taxes and fees
1BR - Short walk to the beach - Colony Inn 46
A heated pool

Enjoy a 3-bedroom vacation home in Yacht Club - Special January & February.

Enjoy a 3-bedroom vacation home in Yacht Club - Special January & February.
Caloosahatchee
9.6 out of 10, Exceptional, (120 reviews)
"We loved our stay"
United States
Nathaniel H.
$401 nightly
The price is $442
Jul 13 - Jul 14
Total with taxes and fees
Enjoy a 3-bedroom vacation home in Yacht Club - Special January & February.
Beach nearby

Stunning Luxury villa Sandpiper across the street from the beach!

Stunning Luxury villa Sandpiper across the street from the beach!
East End
9.0 out of 10, Wonderful, (50 reviews)
"It was great"
United States
Susan H.
$504 nightly
The price is $524
Jun 20 - Jun 21
Total with taxes and fees
Stunning Luxury villa Sandpiper across the street from the beach!
Pool

Lakeside Haven with Heated Pool

Lakeside Haven with Heated Pool
Hancock
9.2 out of 10, Wonderful, (46 reviews)
$381 nightly
The price is $435
Jun 21 - Jun 22
Total with taxes and fees
Lakeside Haven with Heated Pool
Outdoor dining

Luxe 3BR Waterfront Stay in Cape Coral

Luxe 3BR Waterfront Stay in Cape Coral
Mariner
10.0 out of 10, Exceptional, (12 reviews)
"We were pleased with our stay. "
United States
Jamie G.
$337 nightly
The price is $345
Jun 20 - Jun 21
Total with taxes and fees
Luxe 3BR Waterfront Stay in Cape Coral
Outdoor pool, a heated pool

Huge Pool, Close to Beach - Bikes, Beach Gear, Everything You Need!

Huge Pool, Close to Beach - Bikes, Beach Gear, Everything You Need!
Caloosahatchee
10.0 out of 10, Exceptional, (38 reviews)
"We had a great stay and the house is great. "
United States
Craig L.
$319 nightly
The price is $352
Jun 21 - Jun 22
Total with taxes and fees
Huge Pool, Close to Beach - Bikes, Beach Gear, Everything You Need!
Sun loungers, beach towels

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, (40 reviews)
"Very clean and loved the space. Very bright and homey. Loved how well equipped the kitchen was since I was there for Thanksgiving and had to cook a little. Not a far drive from some great spots such as Sanibel Island, Bonita Springs and the outlets for some great shopping. Host was great with communication. Would love to stay again next time I’m in the area. "
United States
Stacy D.
$205 nightly
The price is $226
Jun 19 - Jun 20
Total with taxes and fees
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.
Exterior

Yacht Club Area Gulf Access. All you need away from home!

Yacht Club Area Gulf Access. All you need away from home!
Caloosahatchee
9.8 out of 10, Exceptional, (102 reviews)
"Kelly is an amazing host and checked with us after our arrival to make sure we didn’t need anything. She is quick to respond to questions. We enjoyed staying at her home and the location was close to everything. "
United States
Kathleen C.
$462 nightly
The price is $509
Jun 27 - Jun 28
Total with taxes and fees
Yacht Club Area Gulf Access. All you need away from 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

Hampton Inn & Suites Fort Myers Beach/Sanibel Gateway

Hampton Inn & Suites Fort Myers Beach/Sanibel Gateway

10/10 Excellent
"The room was clean. However, we had to ask to have our room clean."
Latonia 3-night trip
Posted 1 hour ago
Hampton Inn & Suites Fort Myers Beach/Sanibel Gateway

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 $92 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.