Holiday rentals with a pool in Captiva

100+ 5 Star Reviews and Right on The Beach!

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

Value · Location · Outdoor spaces

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!

Value · Family · Getting around

Turtle Escape: Heated Pool, Golf Cart, Pickleball&

💰No nickel & diming - AirBnb & cleaning fees in nightly rate! 🍹 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. 🏖️ Premium Beach Essentials: Chairs, Umbrellas, wagon 💻 High-Speed Starlink Internet 🐶 Pet-Friendly 🛌🏽 Supreme Rest: Westin Heavenly Beds 🧻 Full Amenities: Luxury Toiletries & Supplies 😊 Dedicated 24/7 Local Host Support for a Perfect Stay!!

Family · Location · Check-in

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.✨

Hospitality · View · Cleanliness

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.

Location · Family · Quiet

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

Location · Family · Pool

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. ”

Family · Location · Hot tub

Panoramic Gulf Views | Heated Pool | Beach

🧭 The Compass Rose | Beach Getaway 🌴 Welcome to our 4 bed, 3 bath island retreat. Room for 10 guests with a private heated pool. ✔️Rooftop deck ✔️ Screened in porches ✔️4 king beds and 3 full baths ✔️2 carts, 4 kayaks, beach gear, ping pong, foosball, cornhole and Golden Tee ✔️Gourmet kitchen with oven, cooktop, and multiple fridges ✔️50 yards to the Gulf beach - walk or drive, its your choice Settle in, head for the beach, and enjoy the pool and game spaces at your own pace.

Value · Family · Accuracy

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.

Location · Family · Access

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

Location · Family · Beach

Beach Getaway + Golf Cart & Club Access

BOOKING FALL 2026 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

Value · Family · Decor

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.

Location · Family · Biking