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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Top guest favorite

Apartment in Fort Myers Beach

4.99 out of 5 average rating, 67 reviews

Island Sunshine Poolside Gem

Important Note: This apartment has been totally remodeled from hurricanes in 2024. Everything is perfect here. Beaches are beautiful, pool is relaxing and welcoming. Thankfully the island restaurants and bars are also back up and going in fun island style! Perfectly remodeled bright and cheery poolside apartment. This one truly has it all. From luxury bedding to a fully equipped kitchen to a spacious screen porch right outside the living room door. This dreamy island apartment offers a king me

Guest favorite

Tiny home in Port Charlotte

5 out of 5 average rating, 6 reviews

Minutes to Sand, Dog Friendly, Hot Tub Luxury

Watch the stars from your hot tub! Not camping, not glamping... This is luxury living for less! Private dog friendly property. Hooked up to city water, cold air in all rooms, immediate demand hot water and septic. This slice of paradise is minutes from the sand and has an elegantly appointed private master, two private loft bedrooms, sleeper sofa & 9' vaulted ceilings. Your private retreat includes the use of two kayaks, gazebo, beach chairs, 5G Wi-fi & Netflix, Prime, Paramount. Paradise!

Top guest favorite

Home in Bonita Springs

5 out of 5 average rating, 17 reviews

Casa Bonita by the Sea

Indulge in a dream vacation at our 3-bedroom oasis near one of Florida's top beaches. Inside this brand new home, bask in natural light and chic decor. Unwind on the reclining sofa, step outside to your private paradise with a saltwater pool, infinity spa, and outdoor kitchen. The master suite offers luxury with pool access, soaker tub and shower. Enjoy nearby beach activities, hiking, shopping and dining. Every detail is designed for your relaxation. Book now for the ultimate coastal retreat!

Superhost

Home in Captiva

4.95 out of 5 average rating, 92 reviews

Ocean Views |Fast WiFi & Pool |5 Min 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 Gulf of Mexico Beach ★ Sleeps 8 - (2 Kings, 2 Twins, Sofa Bed) - 3 Bathrooms ★Fast Wifi, Keurig, & Smart TVs ★ Access to Pool, Hot Tub & Grill ★ Pack N Play + Board Games ★ Experienced Hosts - (easy check-in, clear communication, recommendations, clean home) ★★ 3 hurricanes hit the area over the last 2 years but the area is coming back nicely★★

Guest favorite

Cottage in Captiva

4.86 out of 5 average rating, 86 reviews

Cottage Secluded in Palms 1 minute walk to Beach

Actual review left by a Guest “We had a great time in Captiva Island. It's the perfect place to get away for a relaxing, secluded, car-free vacation. Federico's cottage is conveniently located just a short walk to the beach and had all of the amenities we needed to relax and enjoy the trip. Federico was helpful and responsive when I had any questions. I highly recommend staying here if you are looking to disconnect and enjoy pristine beaches with lots wildlife and natural beauty. ”

Guest favorite

Home in North Fort Myers

4.91 out of 5 average rating, 23 reviews

Paradise Found

PARADISE FOUND, you can vacation right here at your own LAKE SIDE PARK! Stunning, peaceful & beautiful waterfront property with your own little island. Fish, bird watch or feed the turtles from your private dock or double arched bridge. Huge back yard for enjoyment & safety of children & pets. Your vacation home has a sunny disposition & soaring ceilings. First floor master suite with sliders to pool/lanai. Two story ceilings in livingroom & gorgeous staircase to guest suites.

Top guest favorite

Home in Fort Myers Beach

5 out of 5 average rating, 63 reviews

Coastal Retreat; paradise found!

Welcome to our tranquil retreat, nestled just minutes away from the pristine shores of Ft Myers Beach and Sanibel. Step inside and be captivated by the inviting ambiance of our thoughtfully designed space. The airy living area welcomes you with its abundant natural light, stylish decor, and comfortable furnishings. Relax on the sofa or enjoy the backyard space as you plan your beach adventures. TV's in every bedroom and living room. We look forward to hosting you!

Guest favorite

Home in Naples

4.96 out of 5 average rating, 69 reviews

Blue Tides Inn

Put away your wool hats, hang up your parkas, and break out the swim trunks, sunglasses and flip flops. There’s no better way to celebrate summer (or escape winter) than with a relaxing beach vacation with a tropical pool. Bring the whole family, roll with a group of friends, or make it a romantic retreat. Whatever the trip, opt for a luxurious vacation rental with all the home amenities you’re used to at home—and some. This incredible beach home has it all!

Superhost

Cottage in Fort Myers Beach

4.89 out of 5 average rating, 28 reviews

DEJA BLUE 1000 FT from Beach Great for Families

1000 ft from the beach No car needed!!!! Walk around town or Trolley Best location on beach Perfect vacation spot, beautiful sunsets Newly renovated Close to time square restaurants and shopping. Relax on landscaped palm tree front patio 3 New flat screen tv’s and Brand new stainless kitchen Beach chairs, umbrella and towels are ready to go to the beach Backyard with grill Let’s book and start your vacation!!!!!!!!!!!!!!!!!!!!!!

Top guest favorite

Home in Naples

4.93 out of 5 average rating, 139 reviews

675 FantaSea | New Heated Resort Pool & Fire Pit

Spend the day outside morning, noon & night and live out your FantaSea vacation! Lounge on the deck or in the heated pool on the sun shelf. On a cool night sit by the fire and relax in the Adirondack chairs. Desirable designer interior with coastal decor has the comfort of home with the feel of the sea. We are just a few minutes away from white sandy beaches with beautiful sunsets, amazing restaurants and upscale shopping centers.

Top guest favorite

Home in Punta Gorda

5 out of 5 average rating, 11 reviews

Stunning! Luxury waterfront home

STUNNING!! LUXURY WATERFRONT HOME - HEATED POOL- Close to Harbor/Fish Village -PREMIER HOST reviews averaging 5.0 since 2018 on other site. -Modern, newly updated home with open layout allowing for enjoyment of the cool waterfront breezes. -Boat dock with very close Harbor access within 10 minutes. -Southern exposure, full sun, heated pool, and waterfront. Oversized pool extends along large portion of rear of home.

Superhost

Home in Cape Coral

4.67 out of 5 average rating, 121 reviews

La venezia beautiful 4 bedroom pool/spa heated

Nicely decorated big spacious rooms comfortable beds close to great restaurants 10 minutes from cape coral beach and 1/2 an hour from fort Myers beach 10 to sun splash water park and great house just to relax and enjoy great pool and spa Now with covid-19 we are taking all the precautions to completely sanitized all areas using all the right products for all your protection