Vacation rentals with a pool in Captiva

The stilt home is surrounded by lush greenery and features a spacious deck with railings. Large windows reflect the blue sky, while palm trees frame the structure. A well-kept lawn adds to the natural beauty, enhancing the home's tropical atmosphere.

5 out of 5 average rating, 56 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

The exterior of the residence showcases a two-story structure, adorned with a welcoming porch and surrounded by tropical landscaping. Palm trees and colorful plants enhance the natural beauty of the entrance, with a stone pathway leading toward the front door.

4.88 out of 5 average rating, 8 reviews

Sea U Soon - Luxury Villa with Heated Pool

Welcome to Sea U Soon- An exceptional residence that exudes quintessential Captiva charm with a decidedly modern flare, featuring handcrafted interior design, a lush outdoor landscape with built in kitchen and heated pool, and a true chef's kitchen with custom banquet. Location, location, location- with soaring gulf and bay views from the rooftop sundeck, and just steps to white sand beaches, shopping and dining, guests will find themselves perfectly positioned to enjoy all that Captiva has to o

A heated community pool is surrounded by spacious sun loungers, set against a backdrop of palm trees and well-maintained greenery. The clear blue water reflects the sky, while a golf course stretches out beyond the pool area, providing an inviting environment for relaxation.

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★★

A bird's-eye view captures a modern two-story home with a metal roof surrounded by lush tropical landscaping. A large heated swimming pool is seen in the foreground, with lounge chairs positioned nearby, emphasizing outdoor relaxation in a serene setting.

5 out of 5 average rating, 11 reviews

" Here Comes The Fun" Absolutely Magnificent! Home

HERE COMES THE FUN! Doo-d-Doo-Doo FUN FUN FUN HERE IT COMES! No detailed has been missed. This is truly a luxury home. HERE COMES THE FUN is a single story 3-bedroom, 3.5 bathroom home. Finished in early 2020 it was built on 2.5 lots or on one half acre of sand. Its location is only a 3.5-minute walk on a white sand path-like road past just 4 houses to the largest beach on the island. There is public access and golf cart parking available there and that isn’t always the case on other streets.

A serene resort-style pool is surrounded by lounge chairs under large blue umbrellas. Palm trees and lush greenery create a tropical ambiance. Bright blue skies with a few scattered clouds complete the inviting outdoor setting, ideal for relaxation and enjoyment.

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

A comfortable living area is furnished with a beige sofa adorned with decorative pillows. A light blue armchair complements the space. Large sliding glass doors reveal a view of the bay, while natural light brightens the room. An abstract painting hangs on the wall.

Apartment in Captiva

5136 Bayside Villas, Captiva

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!

A bright outdoor area is visible, featuring a clear pool surrounded by lounge chairs. The white building is complemented by lush greenery, and a well-maintained, artificial grass area enhances the space. Large windows allow natural light to fill the interior.

4.84 out of 5 average rating, 31 reviews

Fredrickson's Corner

Fredrickson’s Corner is newly renovated (2023) and oozes old school captiva cottage charm! Home is steps to Captiva’s world famous beaches and Village and features 3 bedrooms / 2 baths. Our beach house is tastefully decorated with modern finishes and touches. With vaulted ceilings and numerous windows the sun shines bright. The master suite is large and spacious and the guest rooms offer plenty of comfort for family and guests. Pool and hot tub get amazing sun all day!

4.97 out of 5 average rating, 59 reviews

An aerial view captures a serene coastal neighborhood surrounded by lush greenery, with the beach visible in the distance. The beach house is nestled among palm trees, indicating its close proximity to the shoreline and other scenic homes in the area.

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

5 out of 5 average rating, 4 reviews

A scenic view of tropical vegetation leading to a wide beach area, with soft sand and gentle waves. The sky showcases a mix of clouds and bright blue, creating a peaceful atmosphere. The shoreline is visible in the distance, inviting relaxation and exploration.

Apartment in Captiva

New Luxe Beachfrnt, Specatular Ocean Views + Club!

***ALL NEW, FULLY REMODELED, HIGH END, BEACH FRONT & GULF FRONT - LUXURY TOWNHOUSE - WITH THE ISLAND CLUB AT NORTH CAPTIVA AMENITIES! ***ABSOLUTE PRIME LOCATION SLEEP UP TO 4 ADULTS! PLEASE INQUIRE IF ADDITIONAL GUEST REQUESTS AND UP TO 2 DOGS AS APPROVED Please submit requests with these indicated at the booking request. LOCATED ON THE WHITE SUGAR SAND BUTTERFLY BEACH!

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House rentals with a pool

Home in North Captiva Island

A green tropical-style house is elevated on stilts, featuring a spacious staircase that leads to the front entrance. A golf cart is parked in the foreground, equipped with multiple seats, amidst lush landscaping with palm trees and native plants.

4.89 out of 5 average rating, 62 reviews

Gorgeous Island Paradise *heated pool*golf cart*

Tamara Rating, 5 stars2 weeks ago

This was a great place to stay. place was roomie and clean and had all of the necessities both indoor and out to have a stay!

5 out of 5 average rating, 16 reviews

A large pool area is surrounded by tropical palm trees, with lounge chairs placed along the deck and a shaded seating area in the background. Crystal-clear water reflects the bright blue sky, creating a serene atmosphere for relaxation and enjoyment.

Home in North Captiva

Escape to Saltwater&Sunsets | Beach & Club Pools

DavidRating, 5 stars1 week ago

Great hospitality, great host, great stay… Thanks for welcoming us.

4.5 out of 5 average rating, 4 reviews

A modern villa features a striking exterior with large glass doors and a symmetrical design. The entrance is framed by neatly arranged landscaping and a spacious driveway, providing an inviting approach to the home. A bright blue sky with scattered clouds enhances the overall aesthetic.

Home in Pelican

The Masterpiece, high end, luxurious

UweRating, 5 stars11 months ago

Die Villa ist sensationell schön, sehr gepflegt, bestens ausgestattet und super sauber. Das Team von CoralVilla war super gut erreichbar, wahnsinnig flexibel und dazu noch ausgesprochen nett und professionell. Wir haben uns in der Villa wie zu Hause gefühlt und kommen sehr gerne wieder! Vielen Dank!

4.97 out of 5 average rating, 117 reviews

A clear blue pool is surrounded by a spacious patio, featuring comfortable loungers partially immersed in the water. The inviting outdoor space overlooks the serene canal, while the covered lanai offers additional seating options. Lush palm trees sway gently in the background under a bright sky.

Home in Caloosahatchee

Boater’s Paradise-Stunning Sunsets! Games Room!

AndrewRating, 5 stars3 days ago

Wonderful location and peaceful neighborhood! Our fishing charter picked us up right from the dock as well. Other than getting live bait to fish with, and the occasional trip for groceries, we stayed in, relaxed, and enjoyed just being away. This location is definitely on our short list for next year's trip.

5 out of 5 average rating, 6 reviews

The outdoor pool area is enclosed by a screened lanai, showcasing a tranquil setting with palm trees and water views. Comfortable lounge chairs line the poolside, while the surface reflects the colors of the sunset, providing a serene atmosphere.

Home in Bonita Springs

Luxurious 4-Bed Pool Home with Dock & Gulf Views,

AnnemieRating, 5 stars1 month ago

We had an absolutely great 4 day stay. The house is beautiful and the views are stunning. The description in the listing is completely accurate. We would for sure choose this place again for future stays.

4.98 out of 5 average rating, 123 reviews

Home in Bonita Springs

Luxe Unique: Close to Beach, Hot Tub, Heated Pool

TammyRating, 5 stars1 month ago

We had an amazing stay! The property is just a short drive from the beach and located on a quiet, safe street. Andrew was a fantastic host, super responsive and helpful throughout our stay. The home was spotless and clearly well maintained. The highlight was definitely the beautiful pool and hot tub area, it truly felt like our own private resort oasis. We felt relaxed and right at home the entire time. We’ll definitely be back and highly recommend this place to anyone looking for a peaceful, beachside getaway!

4.97 out of 5 average rating, 108 reviews

The living room features a spacious sectional sofa, providing ample seating. Large glass doors open to the outdoor area, enhancing natural light. A mounted TV displays beach scenery, while a modern fireplace adds a touch of warmth. The room's design promotes comfort and relaxation for guests.

Home in Pelican

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

ChristieRating, 5 stars2 weeks ago

My family had an excellent stay at this location. The neighborhood was and with a beautiful canal view.

4.93 out of 5 average rating, 15 reviews

Home in Sanibel

Mangoes (Left Side)

JudyAnn WRating, 5 stars3 weeks ago

We loved the house! Everything was pristine. Was very accommodating when I asked for a shower chair for my husband.

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Condo rentals with a pool

A screened lanai is visible, featuring a round table and two cushioned chairs. The Gulf of Mexico is seen in the background, framed by palm trees under a bright blue sky. Beach chairs are neatly stacked nearby, enhancing the coastal setting.

Condo in Captiva

4.8 out of 5 average rating, 45 reviews

South Seas Beach Villa 2412

LindseyRating, 5 stars3 months ago

Great place to stay! Super easy access to the beach and a beautiful view of the ocean. The condo was clean and had everything we needed for our stay. We would recommend and stay again!

A spacious swimming pool is surrounded by lounge chairs and tropical landscaping. The multi-story building is visible in the background, featuring large windows and shaded areas. Umbrellas provide additional comfort, while clear blue skies create a bright atmosphere.

4.85 out of 5 average rating, 26 reviews

**Sanibel Island's Best Kept Secret

DianeRating, 5 stars4 weeks ago

Very nice unit. Exactly like the photos . Plenty of room. Arrived late on a Saturday so it was nice to have some staples on hand. ( toilet paper, paper towels , soap, shampoo, waters etc) Plenty of towels and beach supplies. Building G is the closest to the beach which was very pretty and not at all crowded. Very quiet and peaceful. There is still construction going on in some of the 1st floor units but they seemed to begin later in morning and finish up early. It was not a bother at all. The beds were very comfortable. Met some very nice neighbors . Would love to return in the future.

4.94 out of 5 average rating, 102 reviews

A clear view of the pool area is presented, surrounded by a white fence. In the background, a three-story building features multiple balconies with screened areas, framed by lush greenery and palm trees. Gentle clouds can be seen in the bright sky.

Condo in Captiva

South Seas Resort Beach Villa 🌴 On The Beach !

BethanyRating, 5 stars3 weeks ago

We had an amazing stay at this condo for our honeymoon. It was the perfect place to relax together and just enjoy the beach! The condo was extremely nice and it was great to have an umbrella and chairs available to use! Elizabeth was very helpful and had so much information for us and recommendations which was so helpful as first time visitors! The area was beautiful and the pool was also very nice! We cannot wait to come back to Sanibel/Captiva!

A screened lanai features a round glass table surrounded by four wooden chairs with tropical-patterned cushions. Lush palm trees provide a view of the pool area, while bright skies and sunlight enhance the space.

5 out of 5 average rating, 6 reviews

Spectacular Sanibel condo near beach with pool

RobertRating, 5 stars1 week 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!

The open kitchen features white cabinetry, stainless steel appliances, and a large granite countertop that offers ample prep space. Natural light floods the area through windowed shutters, while overhead lighting brightens the room. A modern aesthetic is highlighted by minimalist decor and organized storage.

5 out of 5 average rating, 10 reviews

Loggerhead Cay 332 + Bikes + Paddleboard

BethRating, 5 stars3 months ago

Our week at Loggerhead Cay flew by! Right away we all felt at home. The condo is just as pictured and it was very clean, beautifully done, and so comfortable! We all loved the proximity to the peaceful beach with tons of shells (and easy to get to the beach chairs and other supplies). Caihlin was super helpful with local info and travel tips and went above and beyond as a host with so many details - including a pack n play which sealed the deal for me since that’s so hard to find (my kids were obsessed with the bunk bed and the screened in porch). The showers and soft sheets were soooo relaxing and it was very helpful to have a full kitchen and laundry available. We loved exploring Sanibel and this was a great, comfy home base for our family.

A screened-in balcony offers a view of the Gulf of Mexico, featuring palm trees and lush greenery. Two wooden chairs are positioned to face the scenic coastline, allowing for peaceful relaxation. The expansive glass doors provide access to the living area, enhancing the indoor-outdoor experience.

5 out of 5 average rating, 8 reviews

Stylish 2BR Sanibel condo amazing beach views 5C2

AudreyRating, 5 stars3 weeks ago

We absolutely loved this condo. It was beautiful and so peaceful. We would definitely book this again.

A bright living area features a light grey sofa and matching armchairs adorned with decorative blue pillows. A glass-topped coffee table is positioned in front, and natural light filters in through large sliding doors that open to the balcony, framed by white curtain sheers.

4.86 out of 5 average rating, 77 reviews

Sanibel Island Waterfront Condo!!

PattyRating, 5 stars4 months ago

Staying at Juanita’s place was wonderful. Got to see the sunrise every morning and rode my bike to the beach everyday! I highly recommend staying in the condo as the neighbors were so lovely. In addition the pool was wonderful at the end of each day!

An outdoor area features a large blue pool surrounded by lounge chairs. Lush landscaping with green shrubs and palm trees adds to the setting. Several buildings are visible in the background, enhancing the serene atmosphere.