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)
"We had a wonderful stay. Beautiful home with a peaceful view. Great communication with the host. A nice quiet neighborhood. Would stay again. "
United States
Shauna
The price is CA $218
CA $593 total
includes taxes & fees
Aug 31 - Sep 1
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 $244
CA $520 total
includes taxes & fees
Aug 31 - Sep 1
MALU LANI Inn & Marina

3. 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 $90
CA $221 total
includes taxes & fees
Sep 24 - Sep 25
Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

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 $208
CA $431 total
includes taxes & fees
Sep 23 - Sep 24
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

5. 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 $144
CA $528 total
includes taxes & fees
Sep 1 - Sep 2
Casa Florida 🌴 waterfront home with boat ramp

6. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (295 reviews)
"We had a wonderful visit July 26th-28th. Check in was so easy. We stayed in the flamingo. The flamingo is so cute and charming. We had a wonderful time just relaxing and fishing off the dock with the grandkids. We love the kayaks. Tiny village is the perfect place for a little getaway and we can’t wait to book again."
United States
Heather
The price is CA $152
CA $274 total
includes taxes & fees
Sep 9 - Sep 10
Matlacha Tiny Village

7. 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 $263
CA $540 total
includes taxes & fees
Sep 23 - Sep 24
NEW!! The “WATERSIDE” COTTAGE~With dockage

8. 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 $132
CA $460 total
includes taxes & fees
Sep 7 - Sep 8
Luxe 3BR Waterfront Stay in Cape Coral

9. 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 $131
CA $371 total
includes taxes & fees
Sep 7 - Sep 8
Cozy retreat, NE cape coral oasis 5 mins to restaurants and shopping plaza.

10. 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, (41 reviews)
"The property was nice and the location was great. There was plenty of room to park without having to unhook my trailer which was very convenient. The dock area had plenty of room and the foam pads on the pilings were great with no worry at all of damaging the boat. I would definitely recommend staying here and plan to come back."
United States
Carlos P.
The price is CA $308
CA $724 total
includes taxes & fees
Aug 27 - Aug 28
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

11. Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views

Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views
Captiva
9.0 out of 10, Wonderful, (14 reviews)
"Clean property, easy access. Good kitchen supplies. It was nice to be staying on the island and close to the beach."
United States
Louis
The price is CA $145
CA $643 total
includes taxes & fees
Sep 1 - Sep 2
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views

12. Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach

Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach
Captiva
9.2 out of 10, Wonderful, (31 reviews)
"Very nice condo overlooking waterway. Nice pool and easy in and out. "
United States
William B.
The price is CA $173
CA $657 total
includes taxes & fees
Aug 27 - Aug 28
Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach

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, (19 reviews)
"Host very responsive to questions! Really enjoyed the pool and on site amenities!"
United States
Doug M.
The price is CA $223
CA $627 total
includes taxes & fees
Aug 30 - Aug 31
Ultra Modern Home w Heated Salt water Pool pet friendly

14. Perfect Getaway, Anytime of Year, Sunny, Clean, Spacious & Ideally Located!

Perfect Getaway, Anytime of Year, Sunny, Clean, Spacious & Ideally Located!
Pelican
10.0 out of 10, Exceptional, (36 reviews)
"Yes Great location . Close to stores and restaurants . Pool could have been better if Had a cover temp went down over nite."
United States
Rickie D.
The price is CA $203
CA $599 total
includes taxes & fees
Aug 27 - Aug 28
Perfect Getaway, Anytime of Year, Sunny, Clean, Spacious & Ideally Located!

15. Sunshine POOL Cape Coral Home Centrally Located Great Outdoor Space

Sunshine POOL Cape Coral Home Centrally Located Great Outdoor Space
Caloosahatchee
10.0 out of 10, Exceptional, (22 reviews)
"nice clean, comfortable, quiet location. "
United States
John J.
The price is CA $141
CA $541 total
includes taxes & fees
Sep 14 - Sep 15
Sunshine POOL Cape Coral Home Centrally Located Great Outdoor Space

16. Harbour Tower 414 | Gorgeous Residence with Panoramic Water Views and Secluded Beach

Harbour Tower 414 | Gorgeous Residence with Panoramic Water Views and Secluded Beach
Punta Rassa
9.6 out of 10, Exceptional, (20 reviews)
"Was even better in person than the pictures. The communication with the owners was fantastic and the place was absolutely perfect. The private beach was amazing and loved the staff! We are booking again and is an absolute gem to stay at! Had a manatee swim next to us in the ocean and saw dolphins at sunset! Even a Mama Stingray and her baby swam by! Loved this perfect vacation!"
United States
Misti G.
Harbour Tower 414 | Gorgeous Residence with Panoramic Water Views and Secluded Beach

17. 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, (40 reviews)
"We had a great stay and the house is great. "
United States
Craig L.
The price is CA $149
CA $485 total
includes taxes & fees
Sep 7 - Sep 8
Huge Pool, Close to Beach - Bikes, Beach Gear, Everything You Need!

18. SUNSHINE GETAWAY VACATION RENTALS

SUNSHINE GETAWAY VACATION RENTALS
Fort Myers
8.4 out of 10, Very good, (145 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 $73
CA $348 total
includes taxes & fees
Sep 25 - Sep 26
SUNSHINE GETAWAY VACATION RENTALS

19. Waterfront Home: Private Pool & Stunning Sea Views

Waterfront Home: Private Pool & Stunning Sea Views
Pelican
10.0 out of 10, Exceptional, (8 reviews)
"Home was spotless. Loved the layout and view "
United States
Jo-Ann
The price is CA $165
CA $660 total
includes taxes & fees
Sep 17 - Sep 18
Waterfront Home: Private Pool & Stunning Sea Views
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 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.