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, (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 CA $216
CA $587 total
includes taxes & fees
May 16 - May 17
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

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

Heated Pool, 3 Mi to Dtwn: Cape Coral Escape!
3.0 star property
Pelican
The price is CA $128
CA $498 total
includes taxes & fees
Jun 13 - Jun 14
Heated Pool, 3 Mi to Dtwn: Cape Coral Escape!

Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.

Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.
Diplomat
9.4 out of 10, Exceptional, (23 reviews)
"This property was exceptionally clean and beautifully decorated. We felt very at home here and would highly recommend!"
United States
Laura I.
The price is CA $117
CA $355 total
includes taxes & fees
May 29 - May 30
Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.

Luxe 3BR Waterfront Stay in Cape Coral

Luxe 3BR Waterfront Stay in Cape Coral
Mariner
10.0 out of 10, Exceptional, (12 reviews)
"Good property for stay witj the family."
United States
Matvei M.
The price is CA $146
CA $480 total
includes taxes & fees
May 16 - May 17
Luxe 3BR Waterfront Stay in Cape Coral

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, (72 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
The price is CA $137
CA $432 total
includes taxes & fees
May 17 - May 18
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

Waterfront Condo with Pool & Boat Slip

Waterfront Condo with Pool & Boat Slip
Caloosahatchee
10.0 out of 10, Exceptional, (11 reviews)
"The property was amazing. Everything was clean and perfect for our great little vacation."
United States
Amy G.
The price is CA $134
CA $562 total
includes taxes & fees
May 18 - May 19
Waterfront Condo with Pool & Boat Slip

Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs
Englewood
10.0 out of 10, Exceptional, (52 reviews)
"Apartment was very clean! Lots of outdoor seating options. Nice beach chairs to take to the beach."
United States
Apryl H.
The price is CA $122
CA $413 total
includes taxes & fees
May 17 - May 18
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

Tiki Retreat

Tiki Retreat
Riverbend Country Club
10.0 out of 10, Exceptional, (16 reviews)
"A great place to stay!!! "
United States
shelby S.
The price is CA $178
CA $524 total
includes taxes & fees
Jun 1 - Jun 2
Tiki Retreat

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 CA $184
CA $410 total
includes taxes & fees
May 16 - May 17
Matlacha Tiny Village

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, (50 reviews)
"Great place "
United States
Christine
The price is CA $206
CA $443 total
includes taxes & fees
May 17 - May 18
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

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)
"Had a lovely stay.. close to beach and Food. "
United States
Francis F.
The price is CA $206
CA $444 total
includes taxes & fees
May 18 - May 19
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!

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)
"Couldn’t been better"
United States
Louis
The price is CA $206
CA $430 total
includes taxes & fees
May 16 - May 17
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

SUNSHINE GETAWAY VACATION RENTALS

SUNSHINE GETAWAY VACATION RENTALS
Fort Myers
8.4 out of 10, Very good, (143 reviews)
"Easy location to get where we needed. Clean and spacious."
United States
Chris N.
The price is CA $89
CA $370 total
includes taxes & fees
May 26 - May 27
SUNSHINE GETAWAY VACATION RENTALS

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 CA $79
CA $133 total
includes taxes & fees
Jun 4 - Jun 5
Lazy Cuckoo Inn

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

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

Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!

Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
Pelican
9.6 out of 10, Exceptional, (61 reviews)
"Great place"
United States
Randy W.
The price is CA $115
CA $316 total
includes taxes & fees
May 18 - May 19
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!

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 CA $111
CA $309 total
includes taxes & fees
May 23 - May 24
Modern boho 2bed 2bath home, 8 mins to downtown cape and near beach.

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
10.0 out of 10, Exceptional, (22 reviews)
"Ammenities were great.Everything you need.Bring a carry on and check inWill stay again."
United States
Keenan F.
The price is CA $150
CA $447 total
includes taxes & fees
May 17 - May 18
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

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, (27 reviews)
"Great host, perfect amenities!We would definitely come back!"
United States
Eva Marianne T.
The price is CA $185
CA $420 total
includes taxes & fees
May 19 - May 20
Ellis' Hideaway! Cozy 2-bedroom pool home with WiFi, AC in enjoyable Cape Coral

Sunshine Getaway Vacation Rentals!

Sunshine Getaway Vacation Rentals!
Fort Myers
8.2 out of 10, Very good, (72 reviews)
"Great communication with host. Location was fantastic for us in Ft. Myers with all of our destinations within 10-12 minutes."
United States
Richard O.
The price is CA $80
CA $359 total
includes taxes & fees
May 16 - May 17
Sunshine Getaway Vacation Rentals!
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pineland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 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.