Vacation rentals in Pineland

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Top-rated vacation rentals in Pineland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost

Guesthouse in Bokeelia

4.82 out of 5 average rating, 28 reviews

Adorable & spacious efficiency w/ full kitchen

Relax on island time in this adorable & spacious efficiency. It is equipped with wifi, full kitchen, full bathroom, and full closet. There is also a queen sized bed and futon to accommodate guests. Indoor and outdoor dining options. Charcoal grill on site. Designated outdoor smoking section in rear of efficiency with a firepit. Located just 2 miles from the BEST fishing pier in Southwest Florida. Tour the island and experience local restaurant yummy bites. Please *no pets, smoking, or parties *.

Apr 24 – May 1

R1,672 ZAR per night
Guest favorite

Cottage in Matlacha

4.88 out of 5 average rating, 130 reviews

Mojito Island Cottage

Update: In September we were affected by Hurricane Ian. We had just over 5 feet of flooding in our treasured cottage. We have worked tirelessly to put everything back together. All new tile, walls, electric, lighting, furniture, and we even improved the bathroom! Spacious tropical home with water view from our back yard lanai. Boat Dock with Cleaning Fish Station, BBQ beautiful sunsets with fish jumping in our back yard. New large kitchen and one block from art galleries, restaurants and bars.

Sep 27 – Oct 4

R2,101 ZAR per night
Guest favorite

Cottage in Bokeelia

4.99 out of 5 average rating, 106 reviews

Romantic Getaway “Waterside” Dockage~Canal front

Minutes to open water and Jug Creek Marina! Wait till you see this freshly updated cottage! Bring your boat, or rent one nearby. The dock is shared, but there is plenty of room! Lots of history on this beautiful island, with fishing you’ll be amazed with! Tarpon capital of the world, and Charlotte Harbor moments away! Boca Grande, Cayo Costa, Useppa, North Captiva, Sanibel and Cabbage Key, etc. a short boat ride away! The golf carts/kayaks/boats/bikes are available to rent at local resources!

Jul 4 – 11

R3,846 ZAR per night

Popular amenities for Pineland vacation rentals

Stay near Pineland's top sights

Tarpon Lodge26 locals recommend
Island Girl Charters26 locals recommend
Tarpon Lodge Restaurant18 locals recommend
Safe Harbor Pineland14 locals recommend
Alden Pines Country Club16 locals recommend
Pineland Monument Park4 locals recommend

Other great vacation rentals in Pineland

Guest favorite

Home in Cape Coral

5.0 out of 5 average rating, 7 reviews

The Cape Escape Pet-Friendly Sleeps 7

Aug 12 – 19

R2,371 ZAR per night
Guest favorite

Home in Bokeelia

4.97 out of 5 average rating, 31 reviews

Relaxing island home near marina and boat ramp

Sep 26 – Oct 3

R3,060 ZAR per night
Guest favorite

Apartment in Bokeelia

4.83 out of 5 average rating, 84 reviews

Family & Fisherman Get-a-way

Jul 22 – 29

R2,380 ZAR per night
Guest favorite

Condo in Punta Gorda

4.94 out of 5 average rating, 35 reviews

One bedroom condo overlooking Harbor with Pool

Jul 7 – 14

R2,658 ZAR per night
Guest favorite

Guesthouse in Cape Coral

4.93 out of 5 average rating, 56 reviews

Cute & Cozy

Sep 1 – 8

R1,848 ZAR per night
Guest favorite

Home in Cape Coral

5.0 out of 5 average rating, 10 reviews

Charming private room with terrace

Jun 7 – 14

R1,528 ZAR per night
Guest favorite

Home in Cape Coral

4.97 out of 5 average rating, 38 reviews

Cozy 3BR home in the Cape

Sep 29 – Oct 6

R2,813 ZAR per night
Guest favorite

Condo in Bokeelia

5.0 out of 5 average rating, 14 reviews

Bokeelia Island Breeze

Oct 9 – 16

R2,787 ZAR per night
Guest favorite

Home in Matlacha

5.0 out of 5 average rating, 17 reviews

Bayshore Bungalow - 1 bedroom

Aug 24 – 31

R1,983 ZAR per night
Guest favorite

Home in Bokeelia

4.91 out of 5 average rating, 54 reviews

Cozy Duplex in the Heart of the Island

Nov 14 – 21

R2,415 ZAR per night
Superhost

Apartment in Matlacha

4.86 out of 5 average rating, 42 reviews

Studio#3 The Heart of Matlacha-kayaking access

Apr 11 – 18

R2,701 ZAR per night
Superhost

Home in Matlacha

4.93 out of 5 average rating, 30 reviews

Matlacha Waterfront Fisherman’s Escape

May 9 – 16

R2,423 ZAR per night

Destinations to explore

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  4. Lee County
  5. Pineland