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Pine Island Sound vacation rentals

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Top-rated vacation rentals in Pine Island Sound

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

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Home

4.94 out of 5 average rating, 106 reviews

Welcome to Paradise!

Come visit paradise in this amazing newly remodeled property in Sunset Captiva! Kitchen, appliances, and modern touches coupled with a very private property situated for peace and tranquility. A modern single-family vacation home in a beachfront-to-bayfront community with new tennis/pickleball courts, pool, and marina with new state of the art dock and boat slips. You cannot find a better location to enjoy Captiva Island. Look for the iguanas in the trees that cover the screened in porch!

Home

4.91 out of 5 average rating, 64 reviews

🌴ISLAND TIME! DOCK⚓️POOL🏊🏻‍♀️KAYAKS🛶Boat to Beach🏖 Pets

DIRECT GULF ACCESS HOME - Step back in time, recharge yourself on ISLAND TIME! Pine Island is a laid back Old Florida atmosphere where you can get away from it all. 4 beds, 2 full baths. Steps to your dock & canal. Sandy secluded Beaches are minutes away by BOAT! Island Hopping! Don't have a boat, no worries-water taxis & rentals are plentiful on the Island. Golf cart available for a fee. Steps to private community pool & jet tub! Bikes & Kayaks & Games included.Sit back & relax! It's time 🌴🐠

Home

4.97 out of 5 average rating, 114 reviews

The Pearl Beach House, North Captiva Island,FL

This water-front property offers designer furniture and panoramic views of the Gulf of Mexico throughout the home. Experience unprecedented privacy with direct walking access to the beach, and a very secluded location suitable for couples, friends or families. The property has a Main House and Guest Cottage, both with expansive decking and panoramic windows and doors providing spectacular views of the water and sunsets. StarLink WiFi and Samsung QLED smart TV. We allow dogs up to 50 lbs

Rental unit

5 out of 5 average rating, 22 reviews

Apartment at Treehouse Permaculture Farm

This apartment is on a one-of-a-kind tropical fruit farm. Guests can wander throughout 4 acres of tropical fruit tree groves featuring extremely rare fruits grown as a "Food Forest" using the principles of Permaculture. The apartment has private entrance at poolside. On a paved road in a quiet rural location at the north end of Pine Island, within minutes of Saint James City and Bokeelia! All new kitchen. Queen size bed. Parking for a boat trailer. The large bathroom has a tub and shower.

Condo

5 out of 5 average rating, 19 reviews

Island Time Private Poolside Retreat !

Welcome to Island Time! Enjoy all that Pine Island has to offer from this comfy poolside, waterfront ground level apartment with private entrance and boat dock access. Enjoy lounging at the private pool or BBQing on the patio. 15 miles of bike/walking trails are accessible from the front door, and several waterfront tiki bars and restaurants are within walking distance. Captiva, Sanibel and Fort Myers Beach are a short boat ride away. Explore Cape Coral, Fort Myers and nearby state parks.

Home

4.86 out of 5 average rating, 316 reviews

Almost Sanibel, 5 min. Peace, Privacy & Nature.

Almost Sanibel is in a Peaceful/Quite neighborhood. Bunche Beach 2 miles, Sanibel Island 4 miles, Fort Myers Bch 5 miles. Home is set up as a duplex, with TWO COMPLETELY SEPERATE & PRIVATE entrances, kitchens, living rooms, bedrooms, bathrooms & laundry rooms for COMPLETE PRIVACY. It is a 2 bedroom with 2 King beds, 1 full bathroom & shower with large living room, kitchen & Lanie. Perfect for family or 2 couples! • 1/2 mile to Restaurants and Shopping • FREE High-Speed Wi-Fi and Cable-TV

Home

4.92 out of 5 average rating, 106 reviews

Blue Laguna - Vacation in paradise!

Beautiful and welcoming are just two words to describe this magnificent, 4 story home with heated private pool and sweeping 360 degree water views from the observation deck. Blue Laguna features 3 bedrooms and 3 full baths allowing this home to sleep up to 6 people. Two screened in lanai's so you can sit and enjoy the island breeze and leave the sliding doors open for a true island nature experience during the colder seasons. A golf cart for 4 persons is also included in the rental.

Home

4.95 out of 5 average rating, 282 reviews

Luxurious Escape

Centrally located close to restaurants, supermarkets and malls , is 30 minutes to Fort Myers Beach, Sanibel and Captiva. All amenities provided. Guests that have stayed at this property have stress how clean and spotless is this house, UV system in air conditioner system to eliminate viruses, meticulously cleansed after each guest stay. Beach towels, chairs, umbrella provided. Beach in town 5 minutes from the house. We do not accept pets, service pets or comfort pets owner is allergic.

Home

4.95 out of 5 average rating, 110 reviews

Steps To Private Beach Captiva Retreat Golfcart

Relax and Reconnect at Our Charming North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly (with applicable fees), it’s easily accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach start making memories

Home

4.93 out of 5 average rating, 15 reviews

2 Bedroom Island Oasis Getaway

Hi to all of our past & future guests. Our home is such a great place to stay, we are just steps from the water, fishing & the beautiful sunsets. We have space for your boat or you can rent ours. Completely remodeled home as of March 2022, there is a master bedroom and a 2nd bedroom along with a large bathroom. Guest will have access to the entire house including the lanai, patio, boat dock, boat ramp and parking. We also have an optional boat rental available to you right at the dock

Home

4.85 out of 5 average rating, 626 reviews

Tiny house 5 miles from Sanibel / No cleaning fee!

Tiny Paddle Board House $0 cleaning fee Stay on adventure's doorstep! 5 miles to FMB and Sanibel island (beaches, salt water fishing, paddle boarding, kayaking ). Are guests enjoy free amenities: 1. Coffee/tea/bottled water 2. Bicycles 3. SUP - inflatable paddle boards 4. BBQ gas grill 5. Beach chairs and umbrella 6. Cooler and beach towels 7. Secured Wi-Fi 8. Amazon TV, Netflix, Hulu, Disney +, ESPN+ 9. Parking 2 cars 10. Washer and dryer in house 11. Kids toys and books

Home

5 out of 5 average rating, 7 reviews

Bountiful Bokeelia

Escape the cold! Great rates for March and April 2025, one week minimum, monthly discounts. Forget your worries in this spacious and serene oasis. Professionally decorated, Coastal Chic, extremely quiet, 3 acre fenced and gated property off the beaten path on Pine Island. So close yet so far away! The immediate mainland has all that you could possibly need. The property boasts a unique clean natural swimming pond pool.

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Popular amenities for Pine Island Sound vacation rentals

Laptop-friendly workspace

Air conditioning

Other great vacation rentals in Pine Island Sound

Home

5 out of 5 average rating, 13 reviews

Tropical Family Oasis: Pool, Spa, Golf Cart

Home

4.98 out of 5 average rating, 41 reviews

Hidden Treasure - NEW - Pool - Tiki Bar-Near Beach

Home

4.93 out of 5 average rating, 76 reviews

Villa Luhna 3 Bed / 2 Bath Canalfront Heated Pool

Home

4.74 out of 5 average rating, 19 reviews

House With Pool

Home

4.87 out of 5 average rating, 60 reviews

Beautiful Home/Casa Hermosa

Home

4.98 out of 5 average rating, 59 reviews

Peaceful Pine Island House 🌿 Top Floor

Home

5 out of 5 average rating, 94 reviews

Whole cozy house for group of 4

Home

4.91 out of 5 average rating, 33 reviews

Panoramic Views & Heated Pool!

Destinations to explore