Holiday rentals in Pine Island Sound

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Top-rated holiday rentals in Pine Island Sound

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Top guest favourite
A clear blue pool is surrounded by a spacious patio, featuring comfortable loungers partially immersed in the water. The inviting outdoor space overlooks the serene canal, while the covered lanai offers additional seating options. Lush palm trees sway gently in the background under a bright sky.
Home in Cape Coral
4.97 out of 5 average rating, 132 reviews

Boater’s Paradise-Stunning Sunsets! Games Room!

Renovated lanai! This 3 bed/4 bath home is on the nicest canal with 200+ ft of frontage & gorgeous views of the canal & sunset. The pool, tiki hut & docks have full sun all day. Each bedroom has a private bath & there's a 2 pc powder room off the laundry. The primary has a king bed & walkout to pool. The 2nd bedroom has a queen bed & pool access. Bedroom 3 has a queen & private bath. Fully equipped kitchen with everything you need. And a games room! Enjoy stunning sunsets under the tiki hut.

Top guest favourite
The screened-in pool area features a serene swimming pool with shimmering water, two blue lounge chairs positioned nearby, and views of a wide canal. A thatched-roof Tiki hut can be seen across the water, surrounded by lush greenery.
Home in Cape Coral
4.99 out of 5 average rating, 241 reviews

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

Top guest favourite
A modern living area is highlighted by a spacious white sectional sofa, accented with a mustard yellow pillow. A glass coffee table sits atop a striped rug, while a charming yellow front door adds a pop of color. Decorative oars are mounted on the wall.
Cottage in Bokeelia
4.99 out of 5 average rating, 141 reviews

Romantic Getaway “Waterside” Dockage~Canal front

Also available: airbnb.com/h/aframeausable Minutes to open water and Jug Creek Marina! Wait till you see this freshly updated cottage! Bring your boat, or rent one nearby. There is a dock available here. 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! Jug Creek Marina is steps away with food & music!

Top guest favourite
A bright, airy living area features large windows showcasing panoramic Gulf views. A spacious seating arrangement is positioned around a central coffee table, inviting relaxation. The coastal-inspired decor complements the natural light that floods the space, enhancing the serene atmosphere of the beachfront retreat.
Home in Captiva
5 out of 5 average rating, 13 reviews

Beachfront Oasis w/ Golf Cart and Paddle Boards!

💰No nickel & diming : AirBnb & cleaning fees included! 🤝 local concierge support for a stress-free stay! 🏖️ Beachfront paradise, bordered by untouched nature on both sides— serene, and truly private 🚲 2 bikes + 🛶 2 paddleboards included for island adventures on land and sea 🛺 Golf cart provided for carefree island cruising 🛏️ Oversized primary suite: king bed, lounge areas, desk & full ensuite bath 🏡 Detached casita with private king suite—ideal for guests, couples, or quiet retreats!

Guest favourite
A serene beach scene showcases smooth, soft sands meeting the gentle waves of a turquoise ocean. A piece of driftwood rests in the foreground, complementing the clear blue sky and tranquil waters that stretch into the horizon.
Home in Captiva
4.95 out of 5 average rating, 144 reviews

Steps to Beach Captiva Includes CLUB & Golfcart

HOST PAYS AIRBNB FEE WINTER SPECIALS Golf Cart and Club amenities Included 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(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach STAY WITH US

Superhost
Home in Cape Coral
5 out of 5 average rating, 3 reviews

Villa510~3 En-Suites~Gulf Access, Heated spa~pool

Villa510 is a newly built waterfront retreat ideal for extended stays in Cape Coral. Enjoy peaceful salt canal water views and manatees from the lanai, then relax in your private heated pool and spa—perfect year-round. The outdoor kitchen and lanai create an easy, comfortable daily routine. Inside offers three private en-suite bedrooms, a den with optional airbed, open living space, and TVs in every room. Close to shopping, dining, and beaches—perfect for snowbirds seeking comfort and ease.

Guest favourite
Aerial view of a serene coastal landscape features lush greenery along the shoreline. Gentle waves lap against the sandy beach, with a pier extending into the clear blue water. Bright blue skies complement the tranquil setting, inviting exploration and relaxation.
Home in Cayo Costa
4.93 out of 5 average rating, 27 reviews

Cayo Costa Paradise Found

•This stunning home will be for sale as my wife and I transition to full retirement. • 360”views! • On the beach! • Artsy! .• Sleeps 6 (2 Queen, 2 Twin) • Additional unit on 1st fl. . Hot tub! • Beach combing! • kayaks! • Fishing poles! • Swimming, dolphins,manatees! . Books! . Grill, Utensils, fridge, microwave, plates, cups, glasses • 2 Full bath, 2 1/2 bath, 2 outside showers! • Towels, linens, soap, shampoo! • Fire pit!

Top guest favourite
An outdoor area features a sparkling heated pool surrounded by a screened lanai. Two blue loungers are positioned nearby, and the landscaped yard with green grass and palm trees is visible in the background.
Home in Cape Coral
4.99 out of 5 average rating, 73 reviews

Relaxing Poolside Retreat

Welcome to The Sunny Getaway! Nestled in SW Cape Coral, our charming 3-bedroom, 2-bathroom home offers the perfect blend of comfort and relaxation, complete with a sparkling heated pool. The master suite features a king-sized bed and an en-suite bathroom for added privacy and convenience. Take a dip in the pool to cool off from the Florida sun, or simply soak up the rays on the sun loungers. Tucked away in a quiet neighborhood, this place is sure to help you refresh, relax and recharge.

Top guest favourite
An open living area features a spacious arrangement of light-colored furniture, including a large leather sectional and armchairs. A modern fireplace and flat-screen TV are positioned on a textured feature wall. Natural light floods the space through expansive glass doors that overlook the pool area.
Home
4.98 out of 5 average rating, 49 reviews

Villa Sunset Serenade II

Komplett renoviert und neu eingerichtet! Erleben Sie die schönsten Wochen in der brandneu durch ein professionelles Designerteam komplett renovierten Villa Sunset Serenade II. Das mit einem tollen Lichtkonzept ausgestattete offene Wohnzimmer mit der nagelneuen großen modernen Küche der Ess- und Kochinsel sowie mit Kamin und Großfernseher. Die große italienische Ledercouch mit den großen elektrischen Sessel erlaubt einen tollen Blick auf den breiten Kanal und laden zum genießen ein.

Top guest favourite
A two-story house with a light-colored exterior and a metal roof is showcased under a bright blue sky. Lush tropical landscaping surrounds the property, including palm trees. A paved driveway leads to the two garage doors at the front of the home.
Home in Bokeelia
5 out of 5 average rating, 35 reviews

Peaceful Lakeview Retreat / Screened Porch & Bikes

Escape to a peaceful lakeview retreat on Pine Island. Relax on the breezy screened porch, unwind in the cozy living room, and enjoy two serene bedrooms with smart TVs and comfortable bedding. The home features modern bathrooms, a fully stocked kitchen, fast Wi-Fi, and in-unit laundry for convenience. Pet-friendly and close to trails, marinas, and seafood spots — perfect for birdwatching, biking, fishing, or simply soaking up the island’s quiet charm and natural beauty.

Top guest favourite
A serene waterfront view features private docks with blue canopies, providing shade for two green lounge chairs. A small white boat is visible, securely positioned at the dock. Lush palm trees and a clear blue sky enhance the relaxing outdoor atmosphere.
Home in Saint James City
5 out of 5 average rating, 35 reviews

Tranquility, pool, ocean access, boat lift

Mins to ocean, 2 BR + Den, 3 Baths, private pool, end of Monroe channel, boat lift for up to 21 ft, watch dolphins, fish right off the dock, kayaks, boat ride only mins from Sanibel and Fort Myers Beaches, all the amenities of home + board games, Playstation, 2 adult bikes with helmets. Unwind, enjoy the sunny outdoors with a bar and private pool deck – watch sunsets, sip cocktails, spot dolphins, fish from the docks. Come enjoy waterfront living at its finest!

Top guest favourite
Home in Cape Coral
5 out of 5 average rating, 10 reviews

The Palms on Surfside 1004 - SW Cape Coral

Welcome to The Palms on Surfside, a beautiful and super modern designed home located in SW Cape Coral near the Sandoval Community. This 2023 built home will ensure you a vacation in style. You will never want to leave the huge lanai with lots of seating areas overlooking the canal. Spend time fishing in the canal or just relaxing in the heated pool. The living room has 4 large nesting sliding doors that bring the outside in.

Popular amenities for Pine Island Sound holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Lee County
  5. Pine Island Sound