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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Guest favorite

Cottage in Matlacha

4.88 out of 5 average rating, 133 reviews

Mojito Island Cottage

Update: In September 2022 we were affected by Hurricane Ian. We had just over 5 feet of flooding in our treasured cottage. We have worked tirelessly to put everything back together. All new tile, walls, electric, lighting, furniture, and we even improved the bathroom! Spacious tropical home with water view from our back yard lanai. Boat Dock with Cleaning Fish Station, BBQ beautiful sunsets with fish jumping in our canal. New large kitchen and one block from art galleries, restaurants and bars.

Nov 9 – 16

R2,200 ZAR per night

Guest favorite

Home in Saint James City

4.94 out of 5 average rating, 53 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. 4 seat Golf cart available. Steps to our private community pool & jet tub! Bikes & Kayaks & Games included.Sit back & relax! It's time 🌴🐠

Oct 23 – 30

R2,136 ZAR per night

Guest favorite

Guesthouse in Fort Myers

4.98 out of 5 average rating, 620 reviews

Hints of Key West in Fort Myers' Historic District

Tucked away in tranquil Dean Park Historic District. Built in 1925, this carriage house has been completely renovated in 2016. It is over a garage, there are stairs. Stroll to downtown Fort Myers River District, and enjoy the restaurants, nightlife, and cultural events. Take advantage of all the activities the area has to offer, and at the end of the day come back to this peaceful oasis. Our place can accommodate couples, older child (twin air mattress available), business travelers. No pets.

Jul 9 – 16

R2,535 ZAR per night

Guest favorite

Home in Captiva

4.97 out of 5 average rating, 106 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

Oct 26 – Nov 2

R12,790 ZAR per night

Guest favorite

Home in Captiva

4.92 out of 5 average rating, 100 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.

Oct 13 – 20

R11,784 ZAR per night

Guest favorite

Farm stay in Saint James City

5.0 out of 5 average rating, 45 reviews

Private entire cottage on unique horse farm

Relax and unwind at this private and unique cottage on a beautiful horse farm. Close to dining, shopping, a variety of boating, fishing, and other water activities. Visit the Matlacha Bridge to cast a line with other fishing enthusiasts, or take a leisurely bike ride to tour the island (bikes/helmets provided). Grab a water taxi and visit surrounding sister islands with beautiful, secluded beaches. Please see the host guidebook for places to eat, things to do, and best ways to get there.

Feb 5 – 12

R3,143 ZAR per night

Guest favorite

Guest suite in Matlacha Isles-Matlacha Shores

4.84 out of 5 average rating, 315 reviews

Moon Shell Hideaway

Private entrance to your one bedroom plus den (with queen size sleeper/sofa) apartment attached to main house. Direct access to the Gulf of Mexico. Bedroom has a queen size bed and the den has a queen size sleeper/sofa. The den doubles as your kitchenette and sitting area with double sliding glass doors that open up to the shared pool and dock area. Gas grill and microwave for cooking (no stove). Boat to five restaurants. Visit the Matlacha Art Galleries. Fish off the dock. WELCOME!

Sep 6 – 13

R1,737 ZAR per night

Guest favorite

Home in Matlacha

5.0 out of 5 average rating, 141 reviews

The Secret Island Retreat HeatedPool/4b/open water

Free Heated Pool with open Panoramic Bay Views with Amazing Sunsets from this open layout with 4 bedrooms , a den, 3 bath, 2 car garage. 3200 sq ft. 2nd floor has an oversize owners suite with picture windows over the bay and provides an abundance of space for sitting area or quiet space. Three guests rooms + den. Don't forget to relax & enjoy the breeze on the 2nd story balcony...the perfect retreat. Kayaks, 2 boat lifts, fishing poles, bicycles, games, Grill and much more.

Jul 30 – Aug 6

R8,523 ZAR per night

Superhost

Home in Captiva

5.0 out of 5 average rating, 3 reviews

Turtle Escape: Pool, Beach & Fun!

🍹 Outdoor Oasis: Pool, Bar, Games, TV & Shower 🐚 Beach Access: A Leisurely Stroll Away 🛥️Private Dock Available 🏠 Chic Mid-Century Surf Aesthetic 🛌🏽 Supreme Rest: Westin Heavenly Beds ✅ Gourmet Chef’s Kitchen 🏖️ Premium Beach Essentials: Chairs, Umbrellas & Bikes 🐶 Pet-Friendly 🧻 Full Amenities: Luxury Toiletries & Supplies 💻 High-Speed Internet for Connectivity 😊 Dedicated 24/7 Local Host Support for a Perfect Stay!

Dec 1 – 8

R7,103 ZAR per night

Guest favorite

Apartment in Cape Coral

4.9 out of 5 average rating, 146 reviews

Private Apartment with sunny pool

One-bedroom plus den apartment attached to the main house with private entrance. The apartment has a small kitchenette for basic meal preparation. A large pool is right outside your door! Come relax by the pool & cool off on a hot day. The pool is for your private use. We have a gas BBQ grill located in the fenced yard for your use. Ft. Myers Beach 35 min away Sanibel Beach 45 min away Naples Beaches 60 min away

Jan 24 – 31

R2,463 ZAR per night

Guest favorite

Apartment in Englewood

4.92 out of 5 average rating, 393 reviews

BEACH FRONT Unit w/Pool Sandy Toe's #4

Directly Beach front unit. Listen to the waves, walk the beach, hunt for beautiful shells and prehistoric shark teeth, take a swim in the gulf, watch the dolphins, manatees swim by. You can even try your luck at fishing from your 75 feet of private beach. Life is good! 1 of 5 units for rent, please inquire if interested in another. 3 night minimum stay.

R2,683 ZAR per night

Superhost

Home in Bokeelia

5.0 out of 5 average rating, 3 reviews

Bountiful Bokeelia

Great weekly rates for Summer! 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! All the shopping you need just off island in Cape Coral.

Aug 20 – 27

R1,670 ZAR per night