Vacation rentals in Pine Island Sound

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Top-rated vacation rentals in Pine Island Sound

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

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Top guest favourite
An outdoor space features a screened-in pool area with a rectangular swimming pool and a hot tub. Poolside lounge chairs with blue cushions are arranged around a small table. Lush greenery is visible in the background, enhancing the private ambiance.
Villa in Cape Coral
4.95 out of 5 average rating, 133 reviews

LAST Minute! NEW Villa-Heated Saltwater Pool & Spa

Experience Cape Coral like never before all from this gorgeous 3bedroom, 3bath villa. This elegant villa boasts a vibrant interior decorated with Italian furniture and fully equipped kitchen. Begin your day with a few laps in the private pool before heading to the Yacht Club Public Beach, Sun Splash Family Waterpark or Pine Island to soak up some sun! After adventurous days, continue making memories back home with a family barbecue and a soak in the hot tub or have a movie night with loved ones!

Top guest favourite
A scenic view showcases a private deck featuring a spa and circular seating area, positioned near lush greenery. The serene beach is visible in the background, leading to calm waters under a softly lit sky at sunset, creating a tranquil coastal atmosphere.
Home in Captiva
4.96 out of 5 average rating, 49 reviews

Beachfront North Captiva | Rooftop Deck | Hot Tub

No bridges. No cars. No crowds. Stella Maris sits directly on the Gulf on North Captiva — a private barrier island reachable only by boat. Step off your deck onto white sand. Watch dolphins from your 360° rooftop deck at sunset. 3 bedrooms, each with private en-suite bath. Cathedral ceilings, gourmet kitchen, formal dining with Gulf views, stone fireplace, hot tub, and included golf cart. Dual club access — Safety Harbor Club included; optional Island Club for pools, kayaks, bikes, and pool bar.

Top guest favourite
A two-story beach house features a bright blue exterior and large windows, surrounded by palm trees and lush greenery. A wooden staircase leads to the entrance, with a deck visible on the upper level. The sandy area offers a welcoming beach environment.
Home in Captiva
4.91 out of 5 average rating, 129 reviews

Blue Laguna - Vacation in paradise!

This bright, fully equipped welcoming three‑story home features a private heated pool and a rooftop observation deck with stunning 360‑degree water views. It offers three comfortable bedrooms and three full bathrooms for up to six guests, plus two screened lanais where you can relax in the island breeze and listen to the birds. A four‑seater golf cart is included, so you can easily explore the beaches and sandy paths of beautiful North Captiva Island. Also full access to Island Club amenities!

Top guest favourite
A charming two-story home is surrounded by lush tropical landscaping. The exterior features a bright yellow facade with green accents, complemented by a large screened-in porch on the main level. Concrete walkways lead to the entrance, framed by natural beauty and garden elements.
Home in Sanibel
5 out of 5 average rating, 19 reviews

Island Paradise-The Sandy Banana-across from beach

Relax and enjoy a little taste of paradise in this beautiful home with 3 master suites and a large loft area that has twin beds that double as a sofa, its own coffee bar and mini fridge. Tucked in and surrounded by beautiful sea grapes and palm trees you'll feel like its your own private oasis. Located on the quiet west end of Sanibel Island only a two minute stroll to one of the quietest beaches on the island. You're sure to enjoy nightly sunsets over the Gulf of Mexico during your stay!

Guest favourite
Home in Cape Coral
5 out of 5 average rating, 10 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.

Top guest favourite
A clear blue pool is framed by a screened patio, providing a spacious area for relaxation. White lounge chairs are positioned beside the water, and palm trees are visible in the background, enhancing the tropical feel. A boat dock is seen in the distance.
Home in Cape Coral
4.98 out of 5 average rating, 55 reviews

Close to Cape Harbour western pool and dock, golf

Talk about location! This house is located in southwest Cape Coral close to everything great that Cape Coral has to offer including marina, restaurants, shopping, bike trails, kayaks included etc. Right across the street from Cape Coral's most exclusive neighborhood Cape Harbour. This house has a heated pool facing west for sun all day long and fantastic sunsets, new hot tub, boat dock, and completely remodeled check out the primary bath and all brand-new furnishings including kids stuff.

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 in Cape Coral
4.98 out of 5 average rating, 55 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 scenic view of the canal-side property showcasing a wooden dock with a boat lift, surrounded by lush tropical vegetation. Sun loungers are placed on a manicured lawn, and the house's screened-in porch is visible, highlighting the tranquil waterfront setting.
Home in Bokeelia
5 out of 5 average rating, 48 reviews

Waterfront Oasis with Boat Lift & Hot Tub

Bask in endless sun at our Jugg Creek canal-front home, a stone's throw from Charlotte Harbor and iconic islands like Captiva and Boca Grande. Dive into 'Old Florida' with unspoiled beaches and cute eateries. Watch dolphins from your doorstep and savor rainbow sunsets. Our beautiful cottage boasts a outdoor hot tub and shower, screened in porch, grill, and kayaks with a kayak launch right on the dock. Docking is on us, with a new dock & 10k pound boat lift available April-December.

Top guest favourite
Home in Bokeelia
5 out of 5 average rating, 41 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.

Superhost
Home in Saint James City
5 out of 5 average rating, 6 reviews

Charming 2-BR Home w/ AC, Dock & Peaceful.

Discover this charming 2-bedroom waterfront home in peaceful Saint James City. Each bedroom features a comfortable queen bed, plus a cozy living room with a sofa bed for extra guests. With 2 full bathrooms, everyone enjoys space and privacy. The home offers air conditioning and heating for year-round comfort. Relax indoors, unwind by the water, or plan your next island adventure from this inviting home away from home. We’re always happy to share local recommendations.

Top guest favourite
An open-concept living area is showcased, featuring a modern sectional sofa and a sleek coffee table. Large glass doors lead to the outdoor space, allowing natural light to fill the room. A contemporary dining area with stylish fixtures is visible in the background.
Villa in Cape Coral
5 out of 5 average rating, 66 reviews

BRAND NEW Luxury Villa w/Heated and Chilled Pool

Brand new high-end 3 bedroom 3 bath designer home, elegantly decorated with incredible views and direct no-bridge Gulf access. Come and make your lifetime memories in this elegantly appointed executive villa. Located near Matlacha, Sanibel, Fort Myers, and Naples. Extra wide canal with only trees opposite, a salt water lagoon, and just off the spreader canal means incredible solitude and privacy in your elegant oasis retreat.

Top guest favourite
An outdoor area features a sparkling pool alongside a relaxing jacuzzi, both enclosed within a screened lanai. Comfortable seating is arranged in a lounge area, and a set of wooden chairs is positioned near a small table, surrounded by lush greenery and natural light.
Home in Saint James City
5 out of 5 average rating, 20 reviews

Salt Life Serenity

Canal front property, pet friendly, complete with pool, jacuzzi, and boat dock. 2 King beds with 2 full bathrooms. Den/tv room that pulls out into a comfortable Queen bed. We pride ourselves on having a fully stocked kitchen with multiple coffee makers to make your stay in this newly renovated home one to remember. Enjoy fishing from the dock or watching the manatees as they move with the tides.

Popular amenities for Pine Island Sound vacation rentals

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