A waterfront with palm trees and a boat dock.

Pineland Vacation Rentals

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Our top choices for Pineland vacation rentals

1. 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, (10 reviews)
"Property and house were beautiful, clean, quiet. Everything was top notch. Would definitely book again."
United States
Erik B.
The price is CA $221
CA $594 total
includes taxes & fees
Sep 24 - Sep 25
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

2. 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
The price is CA $252
CA $531 total
includes taxes & fees
Oct 14 - Oct 15
MALU LANI Inn & Marina

3. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (297 reviews)
"So cute and clean nice dock to sit and relax or fish. Kayaks available to use free as well with life jackets paddles, etc. well equipped rental we can’t wait to go again! Great communication with hosts."
United States
Lori
The price is CA $185
CA $311 total
includes taxes & fees
Sep 29 - Sep 30
Matlacha Tiny Village

4. 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
The price is CA $210
CA $333 total
includes taxes & fees
Sep 23 - Sep 24
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

5. NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (51 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.
The price is CA $350
CA $660 total
includes taxes & fees
Sep 29 - Sep 30
NEW!! The “WATERSIDE” COTTAGE~With dockage

6. Casa Florida 🌴 waterfront home with boat ramp

Casa Florida 🌴 waterfront home with boat ramp
Bokeelia
9.4 out of 10, Exceptional, (11 reviews)
"This is our second time staying at this location and we will definitely be back! It is so convenient to have the boat ramp at the house and we love the boat lift. The house and property itself has everything you need and is always clean! "
United States
Morgan P.
The price is CA $175
CA $539 total
includes taxes & fees
Sep 23 - Sep 24
Casa Florida 🌴 waterfront home with boat ramp

7. 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, (42 reviews)
"Excellent!"
United States
Tim A.
The price is CA $311
CA $567 total
includes taxes & fees
Sep 23 - Sep 24
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

8. 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.
The price is CA $91
CA $224 total
includes taxes & fees
Sep 24 - Sep 25
Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

9. The Suites at Fishermen’s Village

The Suites at Fishermen’s Village
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,326 reviews)
"Great place"
United States
Nidia
The price is CA $224
CA $250 total
includes taxes & fees
Oct 4 - Oct 5
The Suites at Fishermen’s Village

10. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,156 reviews)
"Great location"
United States
Nicole
The price is CA $284
CA $316 total
includes taxes & fees
Sep 29 - Sep 30
Island Inn

11. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,917 reviews)
"Great stay."
United States
Angie
The price is CA $198
CA $276 total
includes taxes & fees
Sep 23 - Sep 24
Edison Beach House

12. Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence

Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence
Matlacha
9.8 out of 10, Exceptional, (64 reviews)
"Great stay, would definitely go back! "
United States
Chad N.
The price is CA $650
CA $1,506 total
includes taxes & fees
Sep 29 - Sep 30
Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence

13. 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, (21 reviews)
"Host very responsive to questions! Really enjoyed the pool and on site amenities!"
United States
Doug M.
The price is CA $238
CA $649 total
includes taxes & fees
Sep 23 - Sep 24
Ultra Modern Home w Heated Salt water Pool pet friendly

14. Marina Villa 603 | Spacious Coastal Residence | Great Amenities | Walk to the Beach

Marina Villa 603 | Spacious Coastal Residence | Great Amenities | Walk to the Beach
Captiva
8.6 out of 10, Excellent, (13 reviews)
"We stayed with our 2 grandchildren and loved the location and the full kitchen. "
United States
Cheryl G.
The price is CA $396
CA $962 total
includes taxes & fees
Sep 23 - Sep 24
Marina Villa 603 | Spacious Coastal Residence | Great Amenities | Walk to the Beach

15. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (299 reviews)
"Great place!"
United States
Bruce
The price is CA $69
CA $123 total
includes taxes & fees
Oct 22 - Oct 23
Lazy Cuckoo Inn

16. 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, (3 reviews)
"Quiet, staff friendly, breakfast beautifully presented. Staff very helpful."
United States
Ann
The price is CA $209
CA $315 total
includes taxes & fees
Sep 23 - Sep 24
Hibiscus House Bed Breakfast Citrus Room

17. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,700 reviews)
"Excellent place for children"
United States
Jaime E
The price is CA $474
CA $621 total
includes taxes & fees
Sep 23 - Sep 24
Sundial Beach Resort & Spa

18. 2 Queen Bed|Nsmk|Cape Coral FL

2 Queen Bed|Nsmk|Cape Coral FL
Caloosahatchee
10.0 out of 10, Exceptional, (151 reviews)
"Had a lovely time here!"
United States
Anonymous traveller
The price is CA $86
CA $96 total
includes taxes & fees
Sep 23 - Sep 24
2 Queen Bed|Nsmk|Cape Coral FL

19. Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach

Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach
Captiva
9.6 out of 10, Exceptional, (23 reviews)
"Well kept condo."
United States
Joseph S.
The price is CA $175
CA $770 total
includes taxes & fees
Sep 23 - Sep 24
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach

20. 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)
"House was very clean and looked just like advertised. Had a very comfortable stay and property is close to everything you need. Will definitely come back."
United States
Jennifer B.
The price is CA $124
CA $328 total
includes taxes & fees
Sep 23 - Sep 24
Bright & Airy 2bed 2bath home near downtown/Weekly and monthly discounts!
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?

Tiki Hut Paradise 4-bedroom Bokeelia House w Golf Cart Tesla Charger Island Time: This Pineland vacation home rental has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Pineland?

Expedia has 9 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.