Holiday rentals with a pool in Captiva

A modern coastal house with a blue exterior is surrounded by lush tropical landscaping. The two-story structure features a set of stairs leading to the entrance, with views of the calm waters in the background and a sandy beach just steps away.

5 out of 5 average rating, 79 reviews

Beachfront | Pvt Fishing Dock, Shelling, Sunrises

🏝️Latitude Adjustment on North Captiva 👨‍👩‍👦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,basketball) 🏯4-bedroom, 4.5-bath comfortably sleeps 10 ⭐️2,600 sqft under a/c, 1,400 sqft decking overlooking water 📞Owner available from booking-checkout 👩‍✈️Prof Managed- Luggage/Grocery Serv 🛻Golf Cart Included 🛜High Speed Wifi Contact us today!

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 spacious open-concept living area is showcased, featuring a modern kitchen with an island and sleek cabinetry. Large glass doors provide abundant natural light and views of the outdoors. Rustic wooden beams contrast with the contemporary décor, highlighting both elegance and comfort.

4.92 out of 5 average rating, 66 reviews

AquaLux Smart Home

Unwind in style in this spacious and modern home. Here's what awaits you: Smart Home Technology: Control lights, temperature, and even the front door with voice commands or your smartphone for a seamless experience. Heated Saltwater Pool: Take a refreshing dip in the sparkling pool, perfect for year-round enjoyment. Dedicated Workout Area: Maintain your fitness routine with a private space equipped for exercise. Freshwater Canal Views: Wake up to calming water views and the sounds of nature.

5 out of 5 average rating, 4 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 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, 135 reviews

Steps to Beach Captiva Includes CLUB & Golfcart

HOST PAYS AIRBNB FEE FALL 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

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, 121 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.

5 out of 5 average rating, 3 reviews

Apartment in Sanibel

Sundial E304: Gulf Front Sanibel Island Paradise

BRAND NEW - RIGHT ON THE BEACH! Enjoy stunning direct gulf-front views from nearly every room at this relaxing 3BR coastal retreat. This luxury residence was fully renovated to include a custom expanded kitchen, 2 gorgeous bathrooms, and washer & dryer. Top of the line coastal furnishings in every room. The large master bedroom offers spectacular gulf views & a full-size desk in case you need a quiet space to work. WiFi has been fully upgraded to make streaming and video a breeze.

4.93 out of 5 average rating, 106 reviews

The living area features a spacious light-colored sofa accompanied by a rustic coffee table. Large sliding glass doors allow natural light and views of palm trees outside. A flat-screen TV is positioned against a light-coloured cabinet, while a dining table for two is visible on the lanai.

Condo 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.

4.65 out of 5 average rating, 48 reviews

A light-filled living area features a comfortable white sofa adorned with patterned cushions. An accent chair in a subtle pattern complements the space. A flat-screen TV is mounted on the wall, and sliding doors provide views of the surrounding greenery.

Condo in Captiva

Newly Renovated South Seas Villa with Pool

Gorgeous South Seas Villa, formerly known as Tennis Villa, features panoramic garden views, plush master quarters with Posturepedic bed, a well appointed living area with a flatscreen TV, and robust kitchen equipped with all the essentials. Corner residence overlooking pool and garden from its oversized lanai with ample seating, guests will enjoy proximity to all South Seas has to offer while also being close to downtown Captiva, full of opportunities for adventure and relaxation.

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.

4.85 out of 5 average rating, 33 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!

A collage of views showcases a sunset over the water, the interior of a cozy bedroom with a spacious bed, a pool area with lounge chairs, and a living space featuring large windows that reveal lush palm trees and a serene landscape.

4.95 out of 5 average rating, 93 reviews

Ocean View+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) You deserve to see some Captiva Sunsets at least once in your life!

A spacious kitchen area features a large island with seating for six. The room showcases modern appliances, a stylish backsplash with circular patterns, and an open ceiling enhanced by natural wood beams. Light colors create a bright and inviting environment.

4.98 out of 5 average rating, 44 reviews

Heated Pool, Golf Cart, Pickleball& Close to Beach

🍹 Outdoor Oasis: Pool, Bar, Games, TV & Shower 🐚 Beach Access: A Short Leisurely Stroll Away 🛥️ Shared boat dock - ask about availability. 🎾Access to club with tennis, pickleball. 🏠 Chic Mid-Century Surf Aesthetic 🛌🏽 Supreme Rest: Westin Heavenly Beds ✅ Gourmet Chef’s Kitchen 🏖️ Premium Beach Essentials: Chairs & Umbrellas 🐶 Pet-Friendly 🧻 Full Amenities: Luxury Toiletries & Supplies 💻 High-Speed Internet 😊 Dedicated 24/7 Local Host Support for a Perfect Stay!

Popular amenities for Captiva rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An inviting screened-in patio features a large heated swimming pool surrounded by lounge chairs. Sculptures adorn the sides of the pool, and lush greenery is visible through the expansive windows, offering tranquil views of the outdoors and tranquil ambiance.

5 out of 5 average rating, 76 reviews

Luxe Riverfront Retreat~Pool~Spa~Bar~Tropical Yard

An aerial view of a single-story home surrounded by lush green grass and palm trees. The exterior features a warm-colored roof, colorful landscaping, and a pathway leading to the entrance. An American flag is prominently displayed in the front yard.

4.96 out of 5 average rating, 110 reviews

***Relaxation Awaits*** Heated Saltwater Pool Home

5 out of 5 average rating, 8 reviews

Home in Bonita Springs

Family Oasis | Heated Pool + Beach Gear, Kid Ready

A spacious bedroom features a wooden bed with a light-colored blanket and accent pillows. Natural light streams through two windows and French doors, highlighting the wood flooring and area rug beneath the bed. A decorative lamp and a nightstand add to the room's charm.

4.94 out of 5 average rating, 187 reviews

Surfside Elegance SW Cape Coral Luxe Vacation home

5 out of 5 average rating, 9 reviews

Intervillas Florida - Villa Xanadu

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.

4.97 out of 5 average rating, 118 reviews

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

4.95 out of 5 average rating, 77 reviews

A spacious living area is highlighted by a modern sectional sofa facing a sleek gas fireplace and a wall-mounted television. Oversized patio doors open to a lush outdoor area, enhancing the bright and airy ambiance with views of greenery and patio seating.

Home in Naples Park

751 SeaGlass Elegance · Heated Pool · Walk 2 Beach

The exterior view showcases a modern coastal retreat, highlighting a private pool and spacious outdoor areas. Lush greenery surrounds the property, with sandy paths leading to the beach in the distance. The inviting design is complemented by a clear blue sky that enhances the serene coastal atmosphere.

5 out of 5 average rating, 13 reviews

Brand New! Gulf View, Heated Pool, Club Amenities!

Condo rentals with a pool

Condo in Fort Myers Beach

A contemporary living space features a comfortable sofa and a coffee table adorned with decorative items. Large glass doors open to a private balcony with ocean views, allowing natural light to fill the room. Soft colors and minimalistic decor create an inviting ambiance.

4.98 out of 5 average rating, 48 reviews

Beach Sanctuary Condo

4.83 out of 5 average rating, 6 reviews

The spacious living area showcases plush seating arranged around a coffee table, with a large flat screen TV mounted on the wall. A dining table is positioned nearby, and natural light fills the room through sliding glass doors that lead to a screened porch with views of surrounding greenery.

Condo in Sanibel

Blind Pass A205: Renovated West End Condo by Beach

4.97 out of 5 average rating, 30 reviews

A private lanai is visible, featuring a small table with two chairs positioned for ocean views. The scene includes lush greenery, multiple palm trees, and the Gulf of America beyond. The nearby resort buildings add to the tranquil ambiance of the outdoor space.

Condo in Sanibel

Serene Ocean View Escape at Sundial Resort

4.93 out of 5 average rating, 28 reviews

A spacious terrace features comfortable seating, including a sectional sofa and a coffee table, with vibrant cushions. A large umbrella provides shade, while beautiful landscaping and distant buildings create a serene backdrop under a bright blue sky.

Condo in Cape Coral

Grand Outdoor Patio-Luxury Master, Water Views

4.97 out of 5 average rating, 98 reviews

A spacious living area is captured, featuring a comfortable couch and a stylish armchair. A large television is mounted on an entertainment unit, while a coffee table with decorative items sits in the center. Soft lighting enhances the open layout, inviting relaxation.

Condo in Cape Coral

Luxury Condo by Cape Harbor and Excellent Dining!

4.99 out of 5 average rating, 143 reviews

An open kitchen and dining area features a round glass table surrounded by rattan chairs adorned with tropical patterns. Stainless steel appliances are positioned next to light cabinetry. Expansive windows invite natural light, providing a view of the outdoor scenery.

Condo in Bonita Springs

Casa Bonita - Relax @ The Beach (Newly Remodeled)

4.96 out of 5 average rating, 84 reviews

A wide sandy beach is depicted with gentle waves lapping at the shore. The water transitions from turquoise to light green, under a clear blue sky with scattered clouds. The horizon is visible where the ocean meets the sky, creating a serene coastal view.

Condo in Sanibel

Penthouse Ocean view Condo on Sanibel Beach

4.86 out of 5 average rating, 29 reviews

The living area features a comfortable gray sofa with decorative cushions, a white coffee table, and a dining table with blue cushioned chairs. Large sliding glass doors open to a balcony, allowing natural light to fill the space.

Condo in Captiva

Captiva Bayside Villas 1 Bedroom 2 Bath - sleep 4

Other holiday rentals with a pool

A covered outdoor space features a heated saltwater pool bordered by wide stone tiles. Comfortable lounge seating is seen under an umbrella nearby. Lush greenery and canal views are visible beyond the pool area, offering a serene setting for relaxation.

5 out of 5 average rating, 59 reviews

Coastal Cowgirl - Heated Pool

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

5 out of 5 average rating, 4 reviews

south seas beach cottage 1411

An aerial view showcases a modern villa surrounded by lush green landscaping, with a stone driveway leading to the entrance. The property is positioned along a scenic canal, offering waterfront access, while neighboring houses and boats line the peaceful waterway.

4.93 out of 5 average rating, 30 reviews

Aqua Vista - Luxury Vacation Rental Cape

A spacious living area showcases a light-colored sofa arrangement with blue accent pillows. A contemporary coffee table sits in the center, complemented by a neutral area rug. The open layout reveals a modern kitchen and dining area, with natural light illuminating the space through large windows.

5 out of 5 average rating, 21 reviews

D'Alice, 2 Kingsize BR/1 Queen BR, free WiFi, BBQ

An open living area features a spacious arrangement of light-colored furniture, including a large leather sectional and armchairs. A modern fireplace and flat-screen TV are positioned on a textured feature wall. Natural light floods the space through expansive glass doors that overlook the pool area.

4.98 out of 5 average rating, 43 reviews

Villa Sunset Serenade II

4.96 out of 5 average rating, 96 reviews

The outdoor area features a screened porch with a whirlpool, overlooking a serene lake. Sunlight reflects on the water's surface, creating a tranquil atmosphere. Lush greenery surrounds the space, enhancing the natural beauty of the setting.

Villa in Cape Coral

Villa Lake View, A Stunning House&Spectacular View

4.96 out of 5 average rating, 50 reviews

A spacious living area is highlighted by large windows allowing natural light to fill the room. A comfortable sectional sofa is positioned around a coffee table on a patterned rug, while plants add a touch of greenery. Decorative elements enhance the inviting atmosphere.

Townhouse in Captiva

Sunrise Bay - North Captiva 2 carts!

A serene view of the Gulf can be seen from a balcony, with lush greenery framing the foreground. Palm trees are swaying gently against a vibrant blue sky, while calm waters reflect the inviting colors of the landscape.