Holiday rentals in Captiva

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Top-rated holiday rentals in Captiva

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Guest favourite

Home in Captiva

5.0 out of 5 average rating, 35 reviews

My Sea Shack~ 1 minute to beach, SH Club, G-Cart

Let "My Sea Shack" be your home away from home while you recharge your mind, body and soul on our island oasis, North Captiva! We are an unspoiled, low-key tropical paradise off the coast of Southwest Florida. This means that our beaches are uncrowded, and tourists and traffic are just a mainland memory! Leave your car and your cares at the marina because this island is only accessible by water taxi, boat or private aircraft. Each day, after exploring our paradise (by provided golf cart), let this spacious property welcome you back. Our new stilt home was built in 2018 and is ready to meet all your vacation needs! It features 2 bedrooms and a pull-out couch which will comfortably sleep 6. The master’s over-sized king bed will provide a nightly hug and a warm place to dream. Not tired quite yet...put on some tv and fall asleep while watching your favorite show on the flat screen. The 2nd bedroom can accommodate 3 people eaily with a comfy queen bed and twin. This room also has a flat screen making it a little easier for guests or little ones to doze off. In the morning, start your day off with your cup of coffee or tea on our sprawling deck. Relax and unwind in this comfortable home away from home! Spend your days on our beaches or stay as busy as you’d like with four on-island restaurants, two bars, kayak rentals, fishing charters, private chefs, cabana rentals, craft making opportunities, bicycle rentals, sunset cruises and our favorite - island hopping charters! My Sea Shack also comes with resort like amenities…take a dip in the community pool, play a game of tennis, enjoy priority seating at Safety Harbor’s restaurant -> On The Water or bring your private boat and have access to a boat slip (small daily fee applies). What makes this property TRULY SPECIAL though is the fact that it is only a 2-minute walk to Safety Harbor’s private beach entrance. This beach is so secluded, you will feel like you are on your own private beach. Choose your itinerary, let us take care of the rest~ your next adventure on North Captiva awaits. HOW TO GET TO THE ISLAND AND HOUSE Island Girl Charters has a ferry that runs from Pine Island to North Captiva. At the marina, you can leave your vehicle there. The boat crew will load up your luggage and groceries onto the ferry and you will be on your way..the actual ride is only about 20 minutes long. Many times you will see dolphins trailing behind as you make your way to the island. Upon arriving at the Safety Harbor drop off, our conceirge service will pick you up and load your belongings onto a trailer. If this is the first time, they will be happy to give you a quick tour before taking you to the house. The conceirge service will also take you back to Safety Harbor upon departure. INCLUDED~ Water osmosis system Wifi Netflix, disney +, hulu, amazon prime DVD player Blue-ray player 6 beach chairs Umbrella Beach towels Beach games Sand toys Pickle ball set Grill Propane tank Pack & play Highchair All spices Courant pizza maker (for frozen pizzas) Mixer Can opener Toaster Coffee maker Blender All kitchen cutlery Blowdryer T-fal cookware Vacuum Cleaning supplies Laundry det pods Hand soap Dish soap Toilet paper Paper towels 1 bottle of wine

2–9 Dec

$415 SGD per night

Guest favourite

Home in Captiva

5.0 out of 5 average rating, 65 reviews

Beachfront | Pvt Fishing Dock, Shelling, Sunrises

🏝️Latitude Adjustment on North Captiva!! 💎Newly renovated throughout (2023) 👨‍👩‍👦Family Friendly 🏖️Private Beachfront 🎣Private Fishing Dock w/ Lights for night fishing, best fishing spot! Loaded w/ Snook,Redfish,Trout,Sheepshead &more! 🏊‍♂️Island Club Membership (pools,kayaks,bikes) 🏯4-bedroom, 4.5-bath comfortably sleeps 10 ⭐️2,600 sqft under a/c, 1,400 sqft decking overlooking water 📞Owner avail from booking-checkout! 👩‍✈️Prof Managed- Luggage/Grocery Serv 🛻Golf Cart Included! 🛜High Speed Wifi 🕹️Games

26 Sep – 3 Oct

$912 SGD per night

Guest favourite

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.

31 May – 7 Jun

$158 SGD per night

Superhost

Home in Captiva

4.95 out of 5 average rating, 99 reviews

Welcome to Paradise!

A modern single family vacation home in a beachfront-to-bayfront community with tennis, pool, and marina with dock and boat slip. There are two master bedrooms with king beds, a loft with two twin beds, and a children's room with two bunk beds, so the house can sleep 6 adults and 2 children (under 13 years old) comfortably. There are two full bathrooms. Amenities include 3 cable TVs, WiFi, washer/dryer, ceiling fans, sundeck off of master bedroom, large shaded screened porch and covered parking.

17–24 Aug

$538 SGD per night

Guest favourite

Holiday home in Sanibel

5.0 out of 5 average rating, 15 reviews

Laid-Back Luxury - *Private Pool* - Bowmans Beach!

Retreat to this luxury escape, 12-minute walk to Bowmans Beach! Ideal for multi-family/ generational fun. This 5bd/3ba gem sleeps 10+ in style. Upstairs, King, Queen, & Queen+Single comfort, with a ground-level King+Single setup. Bonus room with fullsize bunks. Unwind in the sunroom's social setting, relax in private pool, stay connected w/Gigabit Wifi. Entertainment with TVs, Ping Pong, Beer Pong, and Corn Hole. Elevate your stay with an optional golf cart, 6 bikes. Your dream getaway awaits!

17–24 Jan

$1,331 SGD per night

Guest favourite

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

26 Oct – 2 Nov

$909 SGD per night

Guest favourite

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.

13–20 Oct

$864 SGD per night

Guest favourite

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!

6–13 Sep

$123 SGD per night

Superhost

Cottage in Captiva

4.88 out of 5 average rating, 34 reviews

SEACLUSION TOO, Tropical Private Vacation Island

North Captiva - ferry only access island!! kayaks and bicycles! Fresh remodel Exceptionally romantic vacation home , authentic Captiva charm in a one level cottage with very private bedrooms and bathrooms Large covered patio leads to huge living room with vaulted ceilings and open kitchen Large windows surrounded by dense vegetation Features gleaming woodwork throughout Great location , walk to the beach No neighbors Only rented through Airbnb Reverse osmosis drinking water!!

22–29 Aug

$469 SGD per night

Superhost

Apartment in Captiva

4.88 out of 5 average rating, 34 reviews

Captiva Sweet Retreat at Bayside Villas

Captiva Paradise. Privately owned premier corner location one-bedroom, two bath Bayside Villa with beautiful lanai view of the marina and pool. Step outside for a Short walk to the fabulous beach and village of Captiva. Enjoy mesmerizing sunsets, beach walks and large pool. Open floor plan with spacious living, dining area, large waterfront lanai, kitchen with breakfast island and roomy bedroom with ensuite bathroom. See other things to note for resort access info.

25 Oct – 1 Nov

$394 SGD per night

Superhost

Apartment in Captiva

4.92 out of 5 average rating, 76 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. Enjoy some of the continents most spectacular ocean sunsets right from your own private balcony.

16–23 Jul

$704 SGD 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!

26 Sep – 3 Oct

$540 SGD per night