Vacation rentals with a pool in Captiva

4.93 out of 5 average rating, 15 reviews

Luxury BeachFront~Fishing Dock~Swim Spa~Shelling~

A Luxury BeachFront home for comfort & elegance, Paraíso features 2 ground-level bedrooms for easy access and 2 separate upstairs bedrooms in the main part of the house, the perfect blend of privacy and togetherness. Equipped kitchen with indoor and outdoor seating. Arrive by ferry & stay in pure island luxury. ✔ 1 King Bed~2 Full Beds~2 Bunk Beds~1 Queen Bed ✔ Heated beachfront swim spa ✔ Private fishing dock ✔ Outdoor BBQ kitchen &dining ✔ping pong, & indoor/outdoor games ✔ Washer/dryer, Wifi

A panoramic view of a sandy beach stretches out towards the horizon under a clear blue sky, dotted with white clouds. Beach chairs are set up along the shore, with lush green vegetation in the foreground, leading to the water's edge.

4.95 out of 5 average rating, 106 reviews

100+ 5 Star Reviews and Right on The Beach!

We are a Superhost for a good reason! Sanibel Siesta looks amazing! Immaculate beachfront, 2BR, 2BA w/garage, nicely updated beachy unit at sand's edge. Amazing views of the Gulf with 5 star ratings! 3-day min. New hurricane windows, freshly painted with ELEVATOR IN BUILDING! Discount for weekly/mo. rentals. BR 1: King bed, en suite, smart TV. BR 2: 2 twin beds, smart TV. Qn. sofa bed in LR. Pool, golf course, bikes, laundry on site. No food or condiments stored in unit. May allow small dog.

A two-story beach house features a bright blue exterior and large windows, surrounded by palm trees and lush greenery. A wooden staircase leads to the entrance, with a deck visible on the upper level. The sandy area offers a welcoming beach environment.

4.9 out of 5 average rating, 124 reviews

Blue Laguna - Vacation in paradise!

This bright, fully equipped welcoming three‑story home features a private heated pool and a rooftop observation deck with stunning 360‑degree water views. It offers three comfortable bedrooms and three full bathrooms for up to six guests, plus two screened lanais where you can relax in the island breeze and listen to the birds. A four‑seater golf cart is included, so you can easily explore the beaches and sandy paths of beautiful North Captiva Island. Also full access to Island Club amenities!

A serene beach scene showcases smooth, soft sands meeting the gentle waves of a turquoise ocean. A piece of driftwood rests in the foreground, complementing the clear blue sky and tranquil waters that stretch into the horizon.

4.95 out of 5 average rating, 145 reviews

Steps to Beach Captiva Includes CLUB & Golfcart

HOST PAYS AIRBNB FEE WINTER SPECIALS Golf Cart and Club amenities Included 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(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach STAY WITH US

5 out of 5 average rating, 9 reviews

A modern living space features a comfortable gray sofa adorned with decorative pillows. Large windows offer views of the outdoors, while a dining area, with a table and chairs, is positioned nearby. A sleek kitchen countertop displays tasteful decor, including a vase with white flowers.

Apartment in Captiva

Amazing Captiva Bayside Villa

Experience the nicest remodeled & decorated coastal 1-bedroom 2-bathroom villa on Captiva! Designed for ultimate relaxation with great bayside water views, all within the South Seas gated community. The villa has a spacious bedroom with a luxurious king bed, living room with a pull-out sleeper sofa, to accommodate guests. Enjoy the scenic bay views and wake-up every morning to amazing sunrises! Walk to the pristine beach and explore fine dining and shops just outside the resort gates

A bright and spacious living area features a cozy seating arrangement with neutral-colored sofas and decorative pillows. A dining table with white chairs sits nearby, complementing a woven pendant light above. Large windows provide natural light and views of the surrounding landscape.

5 out of 5 average rating, 18 reviews

Sunny Sanibel - Gorgeous Loggerhead Walkout Unit

Loggerhead Cay 351 is a fantastic ground floor walk out condo residence in the sought after Loggerhead Cay development of Sanibel`s East End. "Sunny Sanibel" features two spacious bedrooms and bathrooms, a fully equipped kitchen, direct Gulf views, and a walk out patio, this residence is both beautiful and functional! With resort grade amenities including tennis, pickleball, Olympic sized heated swimming pool, shuffleboard, and community grills, guests will surely return year after year!

4.71 out of 5 average rating, 7 reviews

Home in Sanibel

Sanibel Beachfront Condo | Shelling Paradise

Beachfront 2BR/2BA condo on beautiful Sanibel Island, famous for world-class shelling and sunsets. Enjoy Gulf views from the living room and master bedroom. Includes a fully equipped kitchen, open living area with sleeper sofa. Full size washer and dryer are in the unit. The Pool and tennis court are currently under construction Free parking and direct beach access. Perfect for families, couples, or friends looking to relax, explore, and experience the natural beauty of Sanibel Island.

4.94 out of 5 average rating, 111 reviews

South Seas Resort Beach Villa 🌴 On The Beach !

South Seas Beach Villa 2527 is located directly on the beach. The beautiful sunsets over the Gulf of Mexico, along with the condo pool can be viewed from the private lanai. This updated 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. You will have access to the beach, pool, pickleball, tennis courts, beach chairs & towels and BBQ grills located in the front of the unit.

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.

4.86 out of 5 average rating, 37 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!

4.94 out of 5 average rating, 70 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.

4.98 out of 5 average rating, 61 reviews

A heated saltwater pool is enclosed by a spacious screened area, allowing for relaxation and sun exposure. Lounge chairs and vibrant orange seating are positioned beside the water, with views of a tennis court visible through the mesh walls and lush landscaping beyond.

Home in West Gulf Drive

Coastal Chic Island Escape

Just 150 yards from Sanibel's peaceful beach, our home offers unmatched luxury: direct beach access, a heated saltwater pool, private pickleball/tennis court, and sea-view dining. A king suite, additional king bedroom, playful bunk room, and separate apartment provide comfort for all. Perfect for those seeking a serene escape, our home is not suited for loud gatherings or parties. Please help us preserve the tranquility of this special place. 28-day minimum.

Superhost

A light blue beach house is shown, elevated on a foundation with steps leading to a welcoming porch. Lush tropical plants and vibrant flowers surround the front yard, with clear blue skies and sunlit trees in the background.

5 out of 5 average rating, 4 reviews

18 Sunset Captiva 2 BR / 2 BA House w/ King Bed

Welcome to Sunset Captiva #18 – Your Coastal Sanctuary 🌴🌊 Escape to Captiva Island, Florida, and experience the perfect blend of privacy, convenience, and coastal beauty at Sunset Captiva #18. Nestled in the exclusive Sunset Captiva community, this beautifully remodeled home offers a serene island retreat just steps from the beach, pool, and tennis courts.

Popular amenities for Captiva rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 30 reviews

An inviting outdoor space features a heated pool, surrounded by loungers and a covered seating area. A colorful inflatable pool toy is placed in the water. The backdrop includes lush greenery and a vibrant sunset sky, providing a soothing atmosphere for relaxation.

Home in Bonita Shores

Luxury Heated Pool Home-Minutes to Barefoot Beach

4.88 out of 5 average rating, 25 reviews

Home in Cape Coral

Luxury Cape Coral Pool Escape

5 out of 5 average rating, 31 reviews

A screened-in patio area offers a view of a private heated pool surrounded by lush greenery. Comfortable wicker seating is positioned near a glass table adorned with snacks. Sunlight filters through, highlighting the tranquil setting against the backdrop of a colorful sunset.

Home in Bonita Shores

3mins2Beach|ScreenedHeatedPool|Bikes|Office|Fenced

Home in North Captiva Island

4.89 out of 5 average rating, 72 reviews

4.89 out of 5 average rating, 74 reviews

An outdoor patio features a refreshing saltwater pool surrounded by lush greenery and palm trees. Several lounge chairs are arranged around the pool, providing ample seating for relaxation. The space is well-lit by natural sunlight, creating a vibrant outdoor setting.

Home in Cape Coral

Luxe Home Pool!

4.94 out of 5 average rating, 51 reviews

A spacious living area features modern furnishings, large windows allowing natural light, and a comfortable seating arrangement facing a flat-screen TV. An adjacent dining area showcases a large table surrounded by stylish chairs.

Home in Bonita Springs

Vanillasky Luxus-Pool-Villa 2-8 Pax Bonita Springs

5 out of 5 average rating, 13 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 Shores

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

5 out of 5 average rating, 18 reviews

NamaStay - Luxury 4BR w Private Heated Pool

Condo rentals with a pool

Superhost

An inviting living area features a pair of striped sofas and a matching armchair, complemented by decorative pillows. Large glass windows provide expansive views of the water, while mirrored walls enhance the light-filled atmosphere. A decorative coffee table sits at the center, with a small lamp illuminating the space.

4.8 out of 5 average rating, 5 reviews

Mariner Pointe 1013: Island Oasis with Bay Views!

A spacious living area features blue upholstered furniture and striped armchairs, complemented by a glass coffee table. Natural light floods in through large sliding doors, revealing a scenic view of greenery and a balcony. An 82" flat-screen TV is mounted on the wall.

5 out of 5 average rating, 56 reviews

South Seas Serenity Luxury Beach Condo

4.9 out of 5 average rating, 259 reviews

A serene view of the Gulf of Mexico features soft waves lapping against a sandy shore, with clear turquoise water meeting an expansive blue sky. The adjacent image shows the condo's exterior with lush green landscaping, highlighting multiple units in a welcoming and well-maintained setting.

Condo in West Gulf Drive

Rare walkout condo on Sanibel beach

5 out of 5 average rating, 11 reviews

Beachfront with Pool + Bikes Loggerhead 472

Condo in Fort Myers Beach

A private screened-in balcony offers stunning views of the ocean. A round dining table is set for four, featuring blue napkins and fresh fruit. The backdrop showcases the serene turquoise water and clear sky, framed by the building structure on one side.

5 out of 5 average rating, 11 reviews

Gullwing Beach Resort 1002

Condo in Fort Myers Beach

A dining area features a round marble table surrounded by sleek, dark chairs. A vibrant floral arrangement with pink orchids is placed in the center. Natural light floods in through large windows, reflecting off polished marble floors. A stylish chandelier hangs overhead, providing an elegant touch.

5 out of 5 average rating, 18 reviews

Seaside 302 - Beachfront 2BR/2BA - Solmate on FMB

An inviting outdoor patio features a sectional sofa with soft cushions and decorative pillows. A coffee table sits in the center, complemented by a lantern. Large windows provide a view of the pool area and landscaped grounds, allowing natural light to fill the space.

5 out of 5 average rating, 91 reviews

View of Gulf, Steps to Beach@The Turquoise Turtle

A screened lanai is furnished with a small round table and four chairs, providing a cozy dining space. Beach chairs are stored on the wall, with a view of the lush green lawn and distant ocean visible through the expansive glass sliding doors.

4.98 out of 5 average rating, 59 reviews

Sundial G406 - Brand New w/Beautiful Beach Views

Other vacation rentals with a pool

5 out of 5 average rating, 6 reviews

The gourmet kitchen features a spacious layout with modern stainless steel appliances and quartz countertops. Natural light filters through the large windows, illuminating the wood cabinetry. A dining area with a bright table and vibrant décor is visible to the right, blending seamlessly with the open-concept living space.

Cottage in Captiva

south seas beach cottage 1411

An aerial view illustrates a cluster of charming cottages surrounded by greenery, with a pathway leading to beach access. A swimming pool is visible at the center, framed by the inviting outdoor space, while the serene shoreline lies in the background.

4.8 out of 5 average rating, 5 reviews

Gulf views - Sanibel Island - Pet Friendly - SI 09

4.56 out of 5 average rating, 99 reviews

South Seas 3 beds loft top 2floors ON beach/water

4.8 out of 5 average rating, 25 reviews

Captiva Hideaway on Old Lodge Lane

The exterior of the home displays a modern design with a light color palette. A set of wooden stairs leads to the entrance, surrounded by lush palm trees and verdant foliage, providing a tropical ambiance. Clear blue skies create a bright backdrop.

5 out of 5 average rating, 12 reviews

Gumbo Limbo North Captiva

5 out of 5 average rating, 13 reviews

A serene view of the calm bay is captured, featuring gentle waves and lush green foliage lining the shore. The horizon stretches into the distance, blending the water and sky with soft clouds, providing a peaceful backdrop for outdoor activities.

Vacation home in Captiva

Dolphin Bay House Oceanfront with private dock

5 out of 5 average rating, 7 reviews

Home in Sanibel

Seabreeze Sanctuary

A group of four individuals stands on a rooftop deck, gazing at a vibrant sunset over the Gulf of Mexico. The scene captures the tranquility of the beachfront, with soft sand and palm trees framing the view, enhancing the connection to nature.