Holiday rentals in Captiva

5 out of 5 average rating, 55 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

4.89 out of 5 average rating, 18 reviews

Apartment in Captiva

Superb Beachfront Residence at South Seas Resort

Located in the most sought after resort on Captiva, this superb one bedroom one bath residence with gulf facing exposure aims to please even the most discerning of guests. This renovated Beach Villas residence in South Seas Resort features direct beach views, plush master quarters with king bed, a spacious and well appointed living area with pullout sofa for extra guests and a flatscreen TV for those lazy days in, and a robust kitchen featuring a fully equipped inventory. Enjoy the beach with th

4.95 out of 5 average rating, 93 reviews

Ocean Views_Pickleball & 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 & Pickleball ★ 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★★

5 out of 5 average rating, 9 reviews

Waid N Sea-Sprawling Gorgeous Beach House/Pool/Bar

Welcome to the Gorgeous Brand New "Waid N Sea" Beach House! Located on the Barrier Island of North Captiva, this 4 BR, 3 Full Bath, Private Heated Pool Home with Amazing Outdoor Dining and Entertaining Areas is now booking Simply Luxurious Vacation Stays! Temporary Boat Dockage may be available inquire! This Superb Beach House located only steps to the most desirable "Butterfly Beach" offers White Sugar Powdered Sand, Amazing Gulf Ocean Views and Wildlife, and World Class Fishing and Shelling!

4.95 out of 5 average rating, 112 reviews

Welcome to Paradise at CollinsCoveCaptiva!

Welcome to your dream getaway in this beautifully updated, turnkey Key West-style home located in the heart of Captiva Island within walking distance to the village. Nestled in the charming Sunset Captiva community—lined with brick-paver streets—this home offers direct access to award-winning beaches and a private marina on the Bay. Boater’s Paradise? Immediate availability for the brand-new HOA-maintained boat docks. Or spend your days relaxing in the oversized, heated resort-style pool.

4.83 out of 5 average rating, 36 reviews

Flat in Captiva

5136 Bayside Villas, Captiva Island

Welcome to a paradise! Our newly renovated Villa offers a spacious bedroom with a luxurious king bed and a separate living room with a pull-out sleeper sofa, accommodating up to 4 guests. The condo has hot water and is fully equipped. Bring your swimsuit! Enjoy the scenic bay views and watch dolphins and manatees from your window. Walk to the pristine beach and explore fine dining and shops just outside the resort gates. Laundry facilities are conveniently located on the ground level.

4.95 out of 5 average rating, 123 reviews

Steps To Private Beach Captiva Retreat Golfcart

Relax and Reconnect at Our Charming North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly (with applicable fees), it’s easily accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach start making memories!!

4.95 out of 5 average rating, 37 reviews

Beachfront Island Retreat | 360 Views & Privacy!

Stella Maris on North Captiva Island: a luxurious beachfront retreat with unparalleled privacy. This spacious 3-bedroom home with den and separate dining room offers unobstructed Gulf views from every level. Just steps to private beach access. Multi-level design culminates in a rooftop deck with breathtaking 360-degree views—perfect for sunrise and sunset. Features cathedral ceilings, gourmet kitchen, built-in hot tub, and includes a 6-seater golf cart for island exploration. Contact us!

4.94 out of 5 average rating, 102 reviews

Apartment in Captiva

South Seas Resort Beach Villa 🌴 On The Beach !

South Seas 2527 is located in the Beach Villas area of the South Seas Resort, the Gulf of Mexico and pool can be viewed from the private lanai. This second floor unit has one king size bed located in the bedroom and pull out queen size sleeper sofa. The kitchen is fully stocked, there is an inside and outside dining table for your enjoyment. Beach chairs, umbrella and beach towels are provided with this unit since resort amenities are not available when you rent through an owner.

4.97 out of 5 average rating, 58 reviews

Cottage in Captiva

The FlipFlopper Beach House - North Captiva Island

FlipFlopper Beach House - well appointed family focused beach home only a 3 minutes walk from the White Sand Beaches on the Gulf of Mexico and 3 min walk to Island Club Amenities on North Captiva Island. Rate includes Luggage Deliver, use of Golf Cart and Members Access to The Island Club. Hard limit on 6 guests - rare exceptions but please ask - infants are not counted in the above 6 person limit! Private Hot Tub on the rear deck amongst the Sable Palms.

5 out of 5 average rating, 20 reviews

Lookout Escape: Private Island Luxury*Gulf Views

🌅 360° Gulf-to-Bay Views 🎉 Outdoor Paradise: Pool, Bar, Dart Boards, TVs, Games, Outdoor Shower, Bikes+ 🏖️Steps from the Beach! 🍳 Gourmet Kitchen: KitchenAid Appliances & Williams Sonoma Gear 🛥️ Shared boat dock - ask about availability. 🛌 Westin Heavenly Mattresses 🏖 Top-Tier Beach Gear: Chairs, Umbrellas, Cooler & Wagon 🐕 Pets Welcome 🧴 Luxe Amenities: Fine Toiletries & Essentials 🌐 Fast Starlink Internet 😊 24/7 Local Host Support

4.94 out of 5 average rating, 17 reviews

Apartment in Sanibel

"Seaspray" - beachfront, Amazing GULF VIEWS!

Hurricane Update: When Hurricane Ian hit on September 28, 2022 it devastated the island. Many complexes are still recovering. There is a likelihood that you will hear construction noises throughout your stay from our complex or neighboring complexes depending on the dates of your stay. We appreciate you being part of the healing process. There are plenty of local restaurants and shops to experience during your stay! #SanibelStrong

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Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Captiva

Townhouse in Captiva

4.63 out of 5 average rating, 99 reviews

south seas king bed sleeper NOW open renovated

TerriRating, 5 stars3 weeks ago

Wonderful condo! Right on the beach and next to the pool area. Great sunsets! The unit was very clean and had everything we needed. Loved the screened in balcony. Kim as very easy to communicate with.

5 out of 5 average rating, 5 reviews

Beautiful Florida stilt house steps to the beach

CarrieRating, 5 stars1 month ago

We had an amazing stay at this Captiva getaway! The house was beautiful, clean, and had everything we needed for a relaxing vacation. The location couldn’t have been better...just a short walk to the beach and close to shops and restaurants, yet peaceful and quiet. It was the perfect spot to unwind and enjoy all that Captiva has to offer. We’d absolutely stay here again!

4.81 out of 5 average rating, 32 reviews

Home in Sanibel

Premier Beachfront Residence at Villa Sanibel

LisaRating, 5 stars35 months ago

This condo was in a great location. Right on the beach and close to the pool. Close to Bailey’s and restaurants. Very clean and nicely decorated. Great communication with the owner while making reservations, during our stay and after checking out. I will definitely be back.

4.93 out of 5 average rating, 15 reviews

Home in Sanibel

Amazing Getaway with Private Pool

UldaRating, 5 stars11 months ago

Upon arrival in Sanibel, we found the property immaculately clean and beautifully decorated, creating a cozy. Our stay at Ricardo’s place was absolutely fantastic from start to finish. Everything exceeded our expectations. Communication with Ricardo was smooth and prompt, making the booking process hassle-free. The amenities provided were top-notch, ensuring that we had everything we needed for a comfortable stay. The location was perfect. We enjoyed exploring the area and discovered plenty of great dining options nearby. Overall, our experience was nothing short of amazing. We highly recommend Ricardo and his property. Thank you for such a memorable stay we will definitely be back.

5 out of 5 average rating, 4 reviews

Villas in the Air – Elevated Island Living!

JamieRating, 5 stars1 week ago

The place is as wonderful as the photos and description. Getting there was effortless and enjoyable and the host was very responsive to our many needs. There were a few things missing but they corrected them very quickly and we could not expect any better really! Keep in mind that the “convenience store” on the island closes early if they are on holiday or whatever so bring everything you may need including lots of bug spray! Take advantage of every spot in and outside of this property because there are magical little spots everywhere to enjoy! Great hosts! This is worth every penny for our family holiday!

Apartment in Sanibel

5 out of 5 average rating, 6 reviews

Spectacular Sanibel condo near beach with pool

RobertRating, 5 stars6 days ago

We would definitely consider staying here again and tell friends and family about it if they’re ever in Sanibel. It was so helpful to have items available for the beach, as well. The Airbnb was very well put together and welcoming. The only inconvenience was having water shutoff during our stay but we realize it was necessary. it was necessary for the complex. Having Bowman’s beach near by was great!

5 out of 5 average rating, 15 reviews

Windows on the Water "W.O.W."

MattRating, 5 stars3 months ago

North Captiva will not disappoint! Windows on the water is out of this world. Great family vacation with plenty to do. All the logistics were easy to navigate. We will be back! The island club with mango’s is a great addition. Need to add a golf cart to the property though. This will meet your expectations!