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, (7 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 $223
CA $609 total
includes taxes & fees
Jul 8 - Jul 9
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

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 $166
CA $522 total
includes taxes & fees
Jul 14 - Jul 15
Tiki Retreat

Luxury family friendly WATERFRONT home with a POOL, PLAYGROUND, FIREPIT & BEACH

Luxury family friendly WATERFRONT home with a POOL, PLAYGROUND, FIREPIT & BEACH
Fort Myers
9.6 out of 10, Exceptional, (38 reviews)
"Enjoyable stay for our one night. "
United States
Kevin B.
The price is CA $242
CA $658 total
includes taxes & fees
Jul 9 - Jul 10
Luxury family friendly WATERFRONT home with a POOL, PLAYGROUND, FIREPIT & BEACH

SUNSHINE GETAWAY VACATION RENTALS

SUNSHINE GETAWAY VACATION RENTALS
Fort Myers
8.4 out of 10, Very good, (144 reviews)
"This is a beautiful place to stay and it is EXACTLY as pictured in the platform. No surprises and nothing left out. It was clean, space to eat and cook. Nice area to relax and private bedroom. Nice pool for swimming and the residents were pleasant. A great value! Thank you for accommodating us with last minute notice. Will recommend staying with you. "
United States
SUZANNE M.
The price is CA $83
CA $371 total
includes taxes & fees
Jul 11 - Jul 12
SUNSHINE GETAWAY VACATION RENTALS

Beach Bliss~Walk to Beach & Times Square~Private Pool

Beach Bliss~Walk to Beach & Times Square~Private Pool
Fort Myers Beach
10.0 out of 10, Exceptional, (15 reviews)
"Great location, convenient and very well decorated."
United States
Andrea N.
The price is CA $283
CA $706 total
includes taxes & fees
Aug 4 - Aug 5
Beach Bliss~Walk to Beach & Times Square~Private Pool

Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (293 reviews)
"Clean room, good location, easy check in instructions."
United States
Brooklyn
The price is CA $82
CA $138 total
includes taxes & fees
Aug 6 - Aug 7
Lazy Cuckoo Inn

Lakeside Haven with Heated Pool

Lakeside Haven with Heated Pool
Hancock
9.2 out of 10, Wonderful, (47 reviews)
"Fun pool with lake view and breeze. Extremely clean property and pool. Comfortable beds. Wonderful enclosure around pool. Well maintained. Heated pool awesome. "
United States
Rachel L.
The price is CA $125
CA $625 total
includes taxes & fees
Jul 28 - Jul 29
Lakeside Haven with Heated Pool

Tropical King and Queen with Kitchenette in Fort Myers Beach

Tropical King and Queen with Kitchenette in Fort Myers Beach
Siesta Isle
10.0 out of 10, Exceptional, (1 review)
The price is CA $192
CA $242 total
includes taxes & fees
Jul 11 - Jul 12
Tropical King and Queen with Kitchenette in Fort Myers Beach

Times Square Hideaway By FL Vibes

Times Square Hideaway By FL Vibes
Downtown Fort Myers Beach
9.8 out of 10, Exceptional, (34 reviews)
"Great place with a great host! "
United States
Cynthia N.
The price is CA $213
CA $490 total
includes taxes & fees
Jul 8 - Jul 9
Times Square Hideaway By FL Vibes

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,805 reviews)
"As always, loved my stay with this establishment. Beautifully run My granddaughters “wanted to live there “ 😊"
United States
Yvonne
The price is CA $215
CA $295 total
includes taxes & fees
Aug 1 - Aug 2
Edison Beach House

Casa Playa #205- Toes in the Sand - Pet Friendly

Casa Playa #205- Toes in the Sand - Pet Friendly
Fort Myers Beach
10.0 out of 10, Exceptional, (13 reviews)
"The staff was extremely helpful during my stay"
United States
Kendell S.
Casa Playa #205- Toes in the Sand - Pet Friendly

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.
The price is CA $241
CA $726 total
includes taxes & fees
Jul 10 - Jul 11
Yacht Club Area Gulf Access. All you need away from home!

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 CA $219
CA $621 total
includes taxes & fees
Jul 13 - Jul 14
Enjoy a 3-bedroom vacation home in Yacht Club - Special January & February.

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)
"Very clean property and close to shopping and restaurants. "
United States
Kristen M.
The price is CA $138
CA $387 total
includes taxes & fees
Jul 13 - Jul 14
Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.

Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown

Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown
Caloosahatchee
9.2 out of 10, Wonderful, (39 reviews)
"Great place to stay. Clean, nicely decorated and all amenities close by!"
United States
Darrel P.
The price is CA $116
CA $413 total
includes taxes & fees
Jul 11 - Jul 12
Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown

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, (63 reviews)
"Great place"
United States
Randy W.
The price is CA $121
CA $328 total
includes taxes & fees
Jul 8 - Jul 9
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!

Casa Playa #604 - Palm Tree Place

Casa Playa #604 - Palm Tree Place
Fort Myers Beach
10.0 out of 10, Exceptional, (15 reviews)
"The room was lovely! Good location and staff was very friendly and helpful! We would stay here again. "
United States
Mary W.
The price is CA $198
CA $497 total
includes taxes & fees
Jul 9 - Jul 10
Casa Playa #604 - Palm Tree Place

Paradise Vacation Pool Home Last minute $155

Paradise Vacation Pool Home Last minute $155
Pelican
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful place, great host ! Highly recommended ! "
United States
Titus C.
Paradise Vacation Pool Home Last minute $155

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.
The price is CA $144
CA $489 total
includes taxes & fees
Jul 15 - Jul 16
Luxe 3BR Waterfront Stay in Cape Coral

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, (16 reviews)
"Host communication was great. Location was great, would recommend! "
United States
Tori H.
The price is CA $229
CA $643 total
includes taxes & fees
Jul 8 - Jul 9
Ultra Modern Home w Heated Salt water Pool pet friendly
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 11 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.