Holiday rentals in Pine Island Sound

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Top-rated holiday rentals in Pine Island Sound

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Guest favourite

Two turquoise adirondack chairs are positioned beside a small table on a concrete patio overlooking a calm waterfront. A yellow kayak is visible in the water, with palm trees and homes lining the serene canal in the background under a partly cloudy sky.

Home in Matlacha

5 out of 5 average rating, 10 reviews

Small Waterfront Home - kayaking, fishing

Discover the perfect getaway at this charming one-bedroom, one-bathroom waterfront bungalow. Nestled along the serene shoreline, this cozy rental offers a tranquil escape with stunning views and modern amenities, ideal for individuals or couples seeking a peaceful retreat. Centrally location on Matlacha, Florida. Quiet, slow and unique island life living. Hop on a boat or ferry to explore other islands around, just minutes away. Tucked away in a quiet neighborhood with direct access to the water

Top guest favourite

A serene waterfront scene showcases a vibrant sunset, illuminating the sky in shades of orange and pink. Reflections are seen on the calm water, with palm trees framing the view. A paddle board rests on the grass beside a small table and chairs, inviting relaxation.

Home in Saint James City

5 out of 5 average rating, 16 reviews

Charming Waterfront Home on Main Canal

Welcome to our waterfront home with direct access to the gulf! Located in St.James City, Pine Island, this beautifully renovated home, offers a spacious open concept style with two bedroom (Bedroom 1: Queen Bed+Bedroom 2: Bunk Bed (Queen Bottom+Full Top) and two bathrooms. Den with a Queen Size pullout sofa. Sanibel and Captiva Beach are a short boat ride away, area features world class fishing. Marina located on same canal, home has boat lift and dock to tie up to. Paddle board + tandem kayak

Guest favourite

A collage of views showcases a sunset over the water, the interior of a cozy bedroom with a spacious bed, a pool area with lounge chairs, and a living space featuring large windows that reveal lush palm trees and a serene landscape.

Home in Captiva

4.95 out of 5 average rating, 95 reviews

Ocean View, Heated Pool, Pickleball +Walk to Beach

❤We have OVER EIGHTY 5★ Reviews...Book with Confidence❤ ★ 2 Story, 2,115 Sq Ft Home w/ 2 Patios ★ Views of the Ocean on 2 sides ★ 5 Min Walk to Nearly Private Beach ★ Sleeps 8 - (2 Kings, 2 Twins, Sofa Bed) - 3 Bathrooms ★Fast Wifi, Keurig, & Smart TVs ★ Access to Heated Pool, Hot Tub & Pickleball ★ Pack N Play + Board Games ★ Experienced Hosts - (easy check-in, clear communication, clean home) You deserve to see some legendary Captiva Sunrises & Sunsets at least once in your life!

Guest favourite

Apartment in Captiva

5 out of 5 average rating, 6 reviews

2638 Beach Villas- Executive Captiva Condo

Welcome to 2638 Beach Villas—new to our program! This executive-caliber, 3-bedroom, 3-bath beachfront retreat spans over 1,500 sq. ft. and sleeps up to 9 guests (7 in beds + 2 on a sleeper sofa). Enjoy vaulted cedar ceilings with skylights, a private corner-unit location, and premium amenities including a heated pool, pickleball and tennis courts, high-speed Wi-Fi, and outdoor grills—perfect for a premier island getaway.

Superhost

An aerial view captures the charming single-family home with a well-maintained lawn and vibrant landscaping. A spacious driveway leads to the entrance, while nearby canals and trees create a serene backdrop. The pool area is visible through the screened enclosure, enhancing the outdoor experience.

Home in Rotonda West

4.88 out of 5 average rating, 8 reviews

Waterfront Haven: SW Facing Pool and Spa #10

Step into your own waterfront haven as you walk through the front door of this charming 3-bedroom home, where breathtaking views of the canal and Florida's wildlife greet you through the sliding glass doors overlooking the oversized lanai and pool with spa (electrically heated at an additional fee). This tranquil retreat offers the perfect blend of comfort, convenience, and natural beauty for your stay in Rotonda.

Top guest favourite

The private, heated pool is surrounded by a screened enclosure, showcasing lush tropical landscaping. Soft lighting reflects off the water's surface, while an inviting jacuzzi is situated beside the pool. Two lounge chairs are positioned for relaxation in this serene outdoor space.

Home in Fort Myers

4.96 out of 5 average rating, 137 reviews

Coastal Modern Retreat with Heated Pool and Spa

Retreat to paradise in this extra clean and beautifully renovated home centralized to all major Southwest Florida attractions. Splash and play in your private, year-round heated pool or relax and unwind in the bubbles of the jacuzzi. Heating included in price! Less than a 10 minute drive gets you to RSW airport, tons of excellent restaurants, three supermarkets and 4 major shopping malls.

Guest favourite

An outdoor living area is displayed with comfortable seating arranged around a glass-top table. A ceiling fan hangs above, providing airflow. The space opens to a screened enclosure offering a view of the heated saltwater pool, surrounded by lush greenery.

Home in Cape Coral

4.81 out of 5 average rating, 42 reviews

Family-Fun Amenities, Heated Pool - Villa Mercedes

* * New Amenity * * A Hot Tub for your vacation stay Your search is over in this affordable and beautifully maintained home. Peacefully nestled in a sought after neighborhood in SW Cape Coral you will delight in the tranquility a home of this quality will bring to your vacation. The home features over 2300 square feet of living space under air with 4 bedrooms and 2 baths.

Superhost

An outdoor dining area features a large table surrounded by several wicker chairs. A built-in grill and outdoor kitchen are visible, along with ceiling fans providing airflow. Lush greenery can be seen through the screened enclosure, enhancing the sense of an inviting outdoor space.

Villa in Cape Coral

4.8 out of 5 average rating, 15 reviews

Villa Laura, outdoor kitchen, BBQ, Pool/Jacuzzi

Villa Laura sleeps 8 and is in the desirable SW Cape Coral area in a quiet neighborhood with convenient boat access to the Gulf of Mexico. Are you looking for a stunning Gulf Access vacation home in SW Cape Coral with salt water pool and Jacuzzi? Then the Villa Laura is ideal for you! This Villa will delight you. Your dog up to 25 lbs is for a pet fee welcome as well.

Guest favourite

Home in Saint James City

5 out of 5 average rating, 5 reviews

Lime Life Villa, Retro Escape with Hot Tub!

Lime Life Villa – Retro Waterfront Escape in St. James City Welcome to Lime Life Villa, your slice of laid-back island life in sunny St. James City, Florida! Just steps from Tropical Point Park, this charming off-water retreat blends vintage 70s Florida style with modern comforts — perfect for boaters, beach lovers, and anyone chasing that “lime life” vibe.

Guest favourite

A modern living area features a comfortable leather sofa and two armchairs, complemented by a rectangular coffee table. A dining table for four is visible in the background, with contemporary lighting adding warmth to the space. Soft tones and artwork create a relaxed atmosphere.

Apartment in Captiva

4.92 out of 5 average rating, 89 reviews

Stunning Modern Beach front condo - w golf cart!

This beachfront unit has just been renovated from top to bottom. Every square inch from the floors to the doors to the furniture, appliances and the $5000 Prana Sleep mattress! The ocean views from this unit are breathtaking. Includes your own private Golf Car! This beautiful beach front unit is located within the South Seas resort grounds.

Guest favourite

Home in Bokeelia

4.84 out of 5 average rating, 44 reviews

Paradise Found! - 3/2 Pool Home

Escape to our Tropical Oasis in Bokeelia, Pine Island, Florida! This 3-bed pool home offers comfort and style. Enjoy a private pool, lush surroundings, and amenities galore. Minutes from SWFL's best beaches, Cape Coral, Fort Myers, Matlacha, and Pine Island's restaurants and shops. Book now for a perfect blend of relaxation and adventure!

Top guest favourite

A charming yellow house is framed by lush greenery and vibrant red flowers. The inviting porch features a railing, while a pathway leads to the entrance. Tropical palm trees sway gently in the background under clear blue skies.

Home in Bokeelia

5 out of 5 average rating, 29 reviews

Bountiful Bokeelia

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 natural swimming pond. Pet paradise!