Holiday Rentals in Pineland

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Our top choices for Pineland holiday 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, (4 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.
The price is €364
includes taxes & fees
1 Jun - 2 Jun
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

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, (1,211 reviews)
"We had a great stay!!"
United States
Rebecca
The price is €184
includes taxes & fees
9 Jun - 10 Jun
The Suites at Fishermen’s Village- 2 Bedroom Suites

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, (2 reviews)
"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
The price is €231
includes taxes & fees
25 May - 26 May
Hibiscus House Bed Breakfast Citrus Room

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,648 reviews)
"Excellent stay and amenities for families. "
United States
Megan
The price is €409
includes taxes & fees
31 May - 1 Jun
Sundial Beach Resort & Spa

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,752 reviews)
"Perfect location, super clean, exactly what I needed for a long weekend! Would also be great for a longer stay."
United States
Amy Lynn
The price is €235
includes taxes & fees
2 Jun - 3 Jun
Edison Beach House

Sanibel Siesta on the Beach

Sanibel Siesta on the Beach
2.5 star property
Mid Island
9.6 out of 10, Exceptional, (14 reviews)
"Nice quiet property, super clean, great ladies to check you in, it’s like a second home to us when we are there, everything you would need is there to have a lovely time!! Can’t wait to go back"
United States
Hannelore
The price is €580
includes taxes & fees
26 May - 27 May
Sanibel Siesta on the Beach

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (287 reviews)
"Super cute place!! Super clean and comfortable."
United States
Francesca
The price is €227
includes taxes & fees
21 May - 22 May
Matlacha Tiny Village

Bright & Cozy Townhome · Pool & Near Downtown

Bright & Cozy Townhome · Pool & Near Downtown
3.5 star property
Fort Myers
The price is €301
includes taxes & fees
21 May - 22 May
Bright & Cozy Townhome · Pool & Near Downtown

MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property, peaceful, clean rental. Super responsive owner and all the things you need. Perfect location for boaters. Loved this stay and would definitely rent again! "
United States
April
The price is €362
includes taxes & fees
27 May - 28 May
MALU LANI Inn & Marina

Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,135 reviews)
"The place was amazing and the host was very gracious."
United States
Wendy
The price is €363
includes taxes & fees
27 May - 28 May
Island Inn

Ellis' Hideaway! Cozy 2-bedroom pool home with WiFi, AC in enjoyable Cape Coral

Ellis' Hideaway! Cozy 2-bedroom pool home with WiFi, AC in enjoyable Cape Coral
Caloosahatchee
10.0 out of 10, Exceptional, (28 reviews)
"Great host, perfect amenities!We would definitely come back!"
United States
Eva Marianne T.
The price is €264
includes taxes & fees
31 May - 1 Jun
Ellis' Hideaway! Cozy 2-bedroom pool home with WiFi, AC in enjoyable Cape Coral

Gorgeous Marina Villas Residence at South Seas

Gorgeous Marina Villas Residence at South Seas
Captiva
9.2 out of 10, Wonderful, (11 reviews)
"We stayed with our 2 grandchildren and loved the location and the full kitchen. "
United States
Cheryl G.
The price is €700
includes taxes & fees
21 May - 22 May
Gorgeous Marina Villas Residence at South Seas

Hibiscus House Bed Breakfast Inn Parrot Room

Hibiscus House Bed Breakfast Inn Parrot Room
2.0 star property
Fort Myers River District
10.0 out of 10, Exceptional, (2 reviews)
"Easy check in, clean room and very close to many restaurants and bars"
United States
david
The price is €212
includes taxes & fees
1 Jun - 2 Jun
Hibiscus House Bed Breakfast Inn Parrot Room

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.
The price is €389
includes taxes & fees
21 May - 22 May
Enjoy a 3-bedroom vacation home in Yacht Club - Special January & February.

Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (284 reviews)
"Excellent stay. Only complaint was this single ply toilet paper parking was good. Had a nice back patio air-conditioned worked great. Would definitely go back"
United States
Dean
The price is €81
includes taxes & fees
18 Jun - 19 Jun
Lazy Cuckoo Inn

Chic & Cozy River District Townhouse

Chic & Cozy River District Townhouse
Fort Myers River District
10.0 out of 10, Exceptional, (31 reviews)
"Great place to stay. It is in a good location, close to downtown Fort Myers. The owners are good with their communications and very responsive to questions. We will stay there again on our next trip to the area."
United States
Lynn R.
Chic & Cozy River District Townhouse

coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!

coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
West End
9.2 out of 10, Wonderful, (43 reviews)
"Very responsive host. The cottage was roomy and comfortable and had everything you needed to cook. The bikes were nice and an added bonus. Beach was a couple of hundred yards. Nice neighborhood. We would stay here again. "
United States
Geo K.
The price is €434
includes taxes & fees
21 May - 22 May
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!

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.
The price is €200
includes taxes & fees
22 May - 23 May
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.

Heated Pool, 3 Mi to Dtwn: Cape Coral Escape!

Heated Pool, 3 Mi to Dtwn: Cape Coral Escape!
3.0 star property
Pelican
10.0 out of 10, Exceptional, (1 review)
"This place was wonderful! The host is quick to respond to any questions. Cleanliness excellent. The kitchen has anything and everything you could possibly need. We would highly recommend It. Also is a convenient location to the beaches and downtown Cape Coral. We lived in Fort Myers and Cape Coral before hurricane Ian so we were familiar with the area. It’s also located in a very nice neighborhood. Thankyou for a great stay🍊☀️"
United States
Michael
The price is €311
includes taxes & fees
13 Jun - 14 Jun
Heated Pool, 3 Mi to Dtwn: Cape Coral Escape!

Waterfront, 4 Bed, 2 Bath, sleep 8, Gulf access, pool, spa, southern exposure

Waterfront, 4 Bed, 2 Bath, sleep 8, Gulf access, pool, spa, southern exposure
Pelican
9.8 out of 10, Exceptional, (139 reviews)
"We had an amazing stay! Beautiful home, great location and communication was very easy. "
United States
Jamie G.
Waterfront, 4 Bed, 2 Bath, sleep 8, Gulf access, pool, spa, southern exposure
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 holiday rentals

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

Pineland holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pineland holiday rentals we have selected for you start as low as €81 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 holiday 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 holiday.

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 holiday rentals in Pineland?

Yes, there are holiday rentals close to the most popular sights in Pineland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pineland has to offer?

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **: This holiday home rental outside of Pineland is located on the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Pineland?

Expedia has 10 holiday 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 wider area, you’ll find Randell Research Center and Useppa Island.

What are holiday rentals like in Pineland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pineland. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for families.