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.

5.0 out of 5 average rating, 84 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!

ValueFamilyComfort

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.

4.91 out of 5 average rating, 143 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!

LocationValueView

5.0 out of 5 average rating, 3 reviews

Dolphin Cottage | Beach front | Sunset Cruise

🌴 **DOLPHIN COTTAGE | Old Florida Island Escape 🐬 Escape to Dolphin Cottage, a charming waterfront retreat on North Captiva’s peaceful sunrise side. Wake up to stunning Pine Island Sound views, spot dolphins and manatees from the property, explore nearby beaches, fish, shell, and unwind on expansive porches surrounded by nature. 🌊☀️ 🏖️ Private beach access • 🌅 Water views • 🐬 Wildlife • 🌴 Old Florida charm Disconnect, reconnect, and experience North Captiva island life at its best.✨

Getting aroundCleanlinessDecor

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, 99 reviews

Ocean View, Heated Pool, Pickleball +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 Nearly Private Beach ★ Sleeps 8 - (2 Kings, 2 Twins, Sofa Bed) - 3 Bathrooms ★Fast Wifi, Keurig, & Smart TVs ★ Access to Heated Pool, Hot Tub & Pickleball ★ Pack N Play + Board Games ★ Experienced Hosts - (easy check-in, clear communication, clean home) You deserve to see some legendary Captiva Sunrises & Sunsets at least once in your life!

LocationValueAir conditioning

4.87 out of 5 average rating, 108 reviews

Cottage in Captiva

Coral Cottage hidden in Palms short walk to Beach

Actual review left by a Guest “We had a great time in Captiva Island. It's the perfect place to get away for a relaxing, secluded, car-free vacation. Federico's cottage is conveniently located just a short walk to the beach and had all of the amenities we needed to relax and enjoy the trip. Federico was helpful and responsive when I had any questions. I highly recommend staying here if you are looking to disconnect and enjoy pristine beaches with lots wildlife and natural beauty. ”

ValueFamilyLong stay

4.94 out of 5 average rating, 120 reviews

Captiva Beach Villa On The Gulf Beach !

Captiva 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.

LocationFamilyCheckout

4.67 out of 5 average rating, 3 reviews

A spacious living room features towering ceilings and numerous windows, allowing natural light to fill the area. Comfortable seating arrangements include two upholstered chairs and a sofa. A large television is positioned on the wall, and modern wall art enhances the decor.

Townhouse in Captiva

Beach Breeze - 7 houses from the beach!

Only seven houses from the Gulf of Mexico, Beach Breeze is a gorgeous two-story elevated home located on Laika Lane in the heart of Captiva Village and surrounded by lush landscaping. Numerous windows and towering ceilings in the first-floor living room lend an air of spaciousness to the home. Through the sliding glass doors, the screened lanai offers your family options for relaxation with a private heated lap pool. Upstairs, the sun deck is the perfect place to catch some rays

LocationFamilyBeach

5.0 out of 5 average rating, 69 reviews

Seashell Escape: Heated Pool•Golf Cart•Pool•Truste

💰No nickel & diming — AirBnb & cleaning fees in nightly rate! ⭐ Dedicated guest concierge to help you plan your perfect vacation! 🏖️ Stroll to beach: chairs, umbrellas, wagon provided 🏊 Private heated pool 🛥️ Shared boat dock - ask about availability. 🚗Golf cart included! 🍹 Screened-in pool bar 🏓 FUN! Ping pong, cornhole, PlayStation, games 💻 Fast Starlink internet 🐶 Pet-friendly ✅ Fully stocked kitchen 🧴 Plush bedding, luxurious linens & bath amenities

LocationFamilyCondition

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.

4.94 out of 5 average rating, 156 reviews

Beach Getaway + Golf Cart & Club Access

HOST PAYS AIRBNB FEE 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 proximity/ steps to the beach

LocationValueHot tub

5.0 out of 5 average rating, 6 reviews

Sunset Captiva 58

Your family will be close to everything when you stay at this centrally located place. It is a 7 min walk to the beach and the village where you can dine and shop. Has a heated community pool and tennis courts. House has a small side yard where the family can sit and enjoy the outdoors or play games. Bikes are also included, and it comes equipped with beach towels, wagon, umbrella, cooler, fishing poles and beach chairs.Also comes with a 6 seater golf cart.

ValueLocationAmenities

4.5 out of 5 average rating, 52 reviews

Captiva Villa 3212 Serene Condo Walk to the Beach

Serene Captiva Villa, formerly known as Tennis Villa, features panoramic garden views from its oversized lanai with ample seating, plush master quarters with King bed, a well appointed living area with a 55`` flatscreen TV, and a robust kitchen equipped with all the essentials. Enjoy proximity to all Captiva has to offer while also being close to downtown Captiva, full of opportunities for adventure and relaxation.

FamilyLocationCondition

4.85 out of 5 average rating, 33 reviews

Captiva Hide-A-Way 1A

Amazing 2 bedroom upper condo (sleeps 4) overlooking Pine Island Sound. Take the spiral staircase to the pool and boat dock area. Just a short walk away from the beaches, and some of Captiva Island's best restaurants and bars where you can hear live music almost any night. This getaway destination that will soothe away the stresses of everyday hustle & bustle.

LocationFamilyBiking

Popular amenities for Captiva rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 266 reviews

The screened-in pool area features a serene swimming pool with shimmering water, two blue lounge chairs positioned nearby, and views of a wide canal. A thatched-roof Tiki hut can be seen across the water, surrounded by lush greenery.

Home in Pelican

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

LocationValueParking

4.99 out of 5 average rating, 106 reviews

Home in Bonita Beach

"The Mac" Beach House! Premier Location! Pool/Spa

LocationFamilyTV

The Compass Rose is a multi-level home surrounded by lush greenery, showcasing a light blue exterior. A spacious rooftop deck with seating is visible, complemented by multiple balconies offering shaded areas. Palm trees and coastal vegetation frame the property in a relaxing coastal setting.

4.94 out of 5 average rating, 31 reviews

Panoramic Gulf Views | Heated Pool | Beach

FamilyLocationLong stay

4.88 out of 5 average rating, 26 reviews

Home in Sanibel

Sanibel Beachfront Condo | Shelling Paradise

FamilyValueQuiet

5.0 out of 5 average rating, 6 reviews

Home in Sanibel

Luxury Pine Cove 2br Ocean Front

FamilyLocationView

4.89 out of 5 average rating, 19 reviews

Home in Sanibel

Sanibel SUNsation! Pet Friendly, with heated pool!

LocationFamilyBathroom

The exterior of the beach house is showcased, featuring a covered porch with wooden railings and an American flag. Tropical palm trees surround the property, and stairs lead to the elevated entrance, highlighting the inviting design and island charm.

4.94 out of 5 average rating, 66 reviews

2/2 SandDollars, CLUB, Boat Slip

LocationFamilyCheck-in

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.

5.0 out of 5 average rating, 20 reviews

Gumbo Limbo North Captiva

FamilyLocationNearby

Apartment rentals with a pool

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, 121 reviews

100+ 5 Star Reviews and Right on The Beach!

ValueFamilyPets

4.84 out of 5 average rating, 103 reviews

Breakers West B1, Steps to the Beach!

FamilyValueGetting around

A modern living area features a comfortable leather sofa and two armchairs, complemented by a rectangular coffee table. A dining table for four is visible in the background, with contemporary lighting adding warmth to the space. Soft tones and artwork create a relaxed atmosphere.

4.92 out of 5 average rating, 98 reviews

Stunning Modern Beach front condo - w golf cart!

FamilyValueSleep quality

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.

4.88 out of 5 average rating, 34 reviews

Captiva Bayside Villas 1 Bedroom 2 Bath - sleep 4

LocationFamilyIndoor spaces

4.8 out of 5 average rating, 5 reviews

Ocean's Edge - Beachfront Luxury Condo-Golf Cart

FamilyLocationHospitality

4.98 out of 5 average rating, 58 reviews

Gulf-front Penthouse, Lighthouse Sunrises

FamilyLocationIndoor spaces

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.

5.0 out of 5 average rating, 59 reviews

South Seas Serenity Luxury Beach Condo

ValueFamilyAccess

4.92 out of 5 average rating, 12 reviews

Sayana Unit 101 – Steps to Sand & Sunset Views

LocationWalkabilityBiking

Other holiday rentals with a pool

4.86 out of 5 average rating, 64 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.

Flat in Captiva

5136 Bayside Villas, Captiva Island

FamilyLocationBathroom

4.94 out of 5 average rating, 84 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

FamilyLocationTV

5.0 out of 5 average rating, 30 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.

Flat in Captiva

Amazing Captiva Bayside Villa

LocationFamilyBiking

A two-story home is framed by lush greenery, showcasing a light yellow exterior. The property features large windows and a bright blue door, while a covered entryway is supported by white columns. Outdoor stairs lead to the main entrance, enhancing accessibility.

4.91 out of 5 average rating, 69 reviews

Sunset Captiva 48

FamilyLocationNearby

5.0 out of 5 average rating, 80 reviews

1 minute to Beach & Heated Pool, SH Club, G-Cart

ValueFamilySleep quality

Cottage in Captiva

Beach cottage 1411

LocationFamilyDecor

4.92 out of 5 average rating, 13 reviews

A clear view of a circular hot tub is presented, surrounded by patterned brick. Beyond the hot tub, an expanse of sparkling blue water is visible, framed by tropical greenery and lounge chairs. A dock can be seen in the distance against a bright blue sky.

4.86 out of 5 average rating, 7 reviews

Waterfront House Best Location!Private dock!

LocationFamilyCleanliness