Holiday rentals with a pool in Captiva

4.88 out of 5 average rating, 16 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

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, 13 reviews

Gumbo Limbo North Captiva

Located on North Captiva, in Safety Harbor Club, this comfortable home is conveniently located near beaches, pools, & boat docks. Nestled among native palms, Gumbo Limbo has a wildlife-friendly, private setting you will love. Beautiful beaches & refreshing pools are a short walk or 2 minutes by golf cart (included). The island has over 5 miles of pristine sandy beaches to explore. 3 large pools, tennis & pickle ball courts, sea kayaks, bicycles & private beach access are available to guests.

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, 125 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!

5 out of 5 average rating, 6 reviews

Newly Remodeled Home with Pool Steps to the Beach!

🏡 Laika House – Newly Remodeled Private Pool Home Steps from the Beach! 🏖️ 🌟 EXCITING NEW REMODEL! 🌟 Welcome to Laika House, a charming private pool home just steps from Captiva’s white sandy beaches! Located on quiet Laika Lane with no public parking and minimal traffic, this home offers the perfect blend of privacy and convenience. Walk to Captiva Village’s unique shops, top-rated restaurants, and vibrant attractions while enjoying a peaceful retreat surrounded by tropical landscaping.

5 out of 5 average rating, 4 reviews

Modern Captiva Retreat I Pool/Spa I Prime Location

Escape to "Happy Daze," a luxurious retreat in Captiva Village, just steps from pristine beaches, shops, and dining. Recently refreshed, this 5-bedroom, 5.5-bathroom home features a modern design, elegant finishes, and a warm ambiance, perfect for families and groups. Enjoy a private outdoor space with a kitchen, BBQ, pool/heated spa, ping pong, and pool table. Inside, find 10 TVs, beach gear, and high-speed Wi-Fi. Occupancy: 12 Guests Parking: 4 Spots No Pets Allowed Beds: K/Q/Q/F/T/T/T/T

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, 148 reviews

Steps to Beach Captiva Includes CLUB & Golfcart

BOOKING SUMMER 2026 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 proximity to the beach

4.78 out of 5 average rating, 9 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.

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, 94 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!

4.94 out of 5 average rating, 116 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.

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.

4.87 out of 5 average rating, 38 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!

4.98 out of 5 average rating, 62 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.

4.86 out of 5 average rating, 7 reviews

2638 Beach Villas- Executive Captiva Condo

Welcome to 2638 Beach Villas—new to our program! This executive-caliber, 3-bedroom, 3-bath beachfront retreat spans over 1,500 sq. ft. and sleeps up to 9 guests (7 in beds + 2 on a sleeper sofa). Enjoy vaulted cedar ceilings with skylights, a private corner-unit location, and premium amenities including a heated pool, pickleball and tennis courts, high-speed Wi-Fi, and outdoor grills—perfect for a premier island getaway.

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, 57 reviews

A spacious screened pool area is shown, featuring a heated saltwater pool with built-in bench seating. Lounge chairs are positioned along the edge, and a hammock is visible nearby. The outdoor dining area and sectional seating are included, with a 55" Smart TV situated to provide entertainment.

Home in Bonita Shores

Private Palm Oasis - Close to Beach

5 out of 5 average rating, 58 reviews

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

5 out of 5 average rating, 22 reviews

An aerial view captures the surrounding neighborhood of Mangoes, showcasing lush greenery and winding roads. The retreat is positioned prominently among other residences, with the structure featuring a distinctive green roof. The coastline is visible in the distance, highlighting its proximity to the beach.

Home in Sanibel

Mangoes (Right Side)

5 out of 5 average rating, 69 reviews

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

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.

4.92 out of 5 average rating, 26 reviews

Panoramic Ocean Views, Sleeps 10, Heated Pool

4.97 out of 5 average rating, 117 reviews

A screened patio overlooks a serene swimming pool surrounded by lush greenery. Two lounge chairs are positioned nearby, with a small table featuring colorful drinks. A few inflatable toys float in the water, offering a casual ambiance for relaxation.

Home in Bonita Springs

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool

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.

4.92 out of 5 average rating, 49 reviews

2/2 SandDollars, CLUB, Boat Slip

4.92 out of 5 average rating, 120 reviews

A resort-style pool area is showcased with a stone patio, featuring several lounge chairs and two shaded umbrellas. Palm trees stand nearby, and a rock formation is visible within the pool's edge, complementing the serene outdoor setting.

Home in Iona

Experience of a lifetime

Apartment rentals with a pool

Apartment in West Gulf Drive

An aerial view captures the beachfront setting of Pine Cove #102, revealing direct access to the sandy shore and turquoise waters. Adjacent properties are visible, surrounded by lush greenery, with sunlight casting a warm glow over the landscape. The inviting beach stretches along the coastline.

5 out of 5 average rating, 3 reviews

Pine Cove #102 is a 3/2 beachfront Sanibel vacatio

A marina view is presented through a screened lanai, with several boats docked along the tranquil waters. Lush greenery and palm trees frame the scene, complemented by a pastel sky reflecting the warm hues of sunset.

4.92 out of 5 average rating, 59 reviews

Captiva Sweet Retreat at Bayside Villas

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, 16 reviews

Spectacular Sanibel condo near beach with pool

4.91 out of 5 average rating, 32 reviews

Pointe Santo of Sanibel Unit D32

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, 93 reviews

View of Gulf, Steps to Beach@The Turquoise Turtle

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.

4.97 out of 5 average rating, 33 reviews

Amazing beach views - Sanibel - Sandalfoot 5C2

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!

4.67 out of 5 average rating, 3 reviews

South Seas Beach Villa 2237 - Beach Front

Other holiday rentals with a pool

5 out of 5 average rating, 8 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 of a beachfront home is presented, showcasing its expansive layout surrounded by lush greenery. The property features a pool adjacent to a patio, with a glimpse of the coastline and the Gulf beyond. Nearby palm trees enhance the tropical ambiance.

5 out of 5 average rating, 4 reviews

Sandy Feet North Captiva Island Beach House

A comfortable outdoor seating area features a large sectional sofa adorned with decorative cushions. A coffee table is centered on a patterned rug. In the background, a private pool is visible through a white fence, surrounded by lush greenery.

5 out of 5 average rating, 10 reviews

Island paradise. Hakuna Matata.

A spacious waterfront home is elevated on stilts, featuring a large deck with multiple seating areas. A set of white lounge chairs is positioned on the sandy ground in front, with lush greenery and a clear blue sky enhancing the serene atmosphere.

4.67 out of 5 average rating, 9 reviews

Sanderella

Home in North Captiva Island

A cozy children's bunk room features a wooden ladder leading to an elevated sleeping area. A spacious bed is located underneath, while light-colored bedding complements the shiplap walls. A framed motivational quote decorates the wall, providing a playful touch to the inviting space.

4.89 out of 5 average rating, 72 reviews

5 out of 5 average rating, 18 reviews

An aerial view of a coastal neighborhood reveals well-appointed homes bordering a serene harbor. Lush greenery surrounds the area, while boats are docked at a nearby marina. The tranquil water reflects the clear blue sky, contributing to a calming seascape.

Townhouse in Captiva

Casita Salida del Sol-Waterfront

4.8 out of 5 average rating, 86 reviews

A beach cottage-style home is elevated on stilts, surrounded by lush palm trees. The exterior features a light-colored facade, large windows, and a balcony with railing on the upper level. A clear blue sky serves as the backdrop, enhancing the overall coastal atmosphere.

Cottage in Captiva

Turtle Trax

A spacious living area is presented with two large brown sofas facing each other, complemented by two cream-colored armchairs. A central coffee table sits in between. Large glass doors provide views of the outdoor space, while a television is mounted on the wall, adding to the modern design.