Beachfront holiday rentals in Captiva

Beachfront North Captiva | Rooftop Deck | Hot Tub

No bridges. No cars. No crowds. Stella Maris sits directly on the Gulf on North Captiva — a private barrier island reachable only by boat. Step off your deck onto white sand. Watch dolphins from your 360° rooftop deck at sunset. 3 bedrooms, each with private en-suite bath. Cathedral ceilings, gourmet kitchen, formal dining with Gulf views, stone fireplace, hot tub, and included golf cart. Dual club access — Safety Harbor Club included; optional Island Club for pools, kayaks, bikes, and pool bar.

Sundial I101: Beach Front 1BR w/Garden Views

Right on the beach w/no stairs to climb! Enjoy ground floor living at its best in this relaxing coastal retreat, just steps to the beach. This large 1BR condo sleeps 5 and was fully renovated to include a custom kitchen & bathroom w/large walk-in shower. Top of the line coastal furnishings in every room. The spacious master bedroom offers a Stearns and Foster king bed and a full-size desk if you need a quiet space to work. WiFi has been fully upgraded to make streaming and video a breeze!

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.

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!

Pearl, brand new old island charm

Pearl is a cottage duplex hidden on a private access lane, beautifully and newly decorated. An Island retreat surrounded by tropical vegetation, bathed in sun, and gaurded by waters and waves that seduce you into forgetting the laundry you still have to do at home. Walkability score, 10. Pearl rests less than 3 blocks from Captiva Village. Searing sunrises, alfresco dining, the beach, island shops, live music, and fiery sunsets await you. Ice cream is plentiful and there’s even a Starbucks

Cayo Costa Paradise Found

•This stunning home will be for sale as my wife and I transition to full retirement. • 360”views! • On the beach! • Artsy! .• Sleeps 6 (2 Queen, 2 Twin) • Additional unit on 1st fl. . Hot tub! • Beach combing! • kayaks! • Fishing poles! • Swimming, dolphins,manatees! . Books! . Grill, Utensils, fridge, microwave, plates, cups, glasses • 2 Full bath, 2 1/2 bath, 2 outside showers! • Towels, linens, soap, shampoo! • Fire pit!

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.

NEW 354 Gulf Water Views + CoolCabana +Beach Items

Welcome to the new Loggerhead Cay 354, a tropical retreat on beautiful Sanibel Island where lush vegetation, swaying palms, and clear blue Gulf waters create the feeling of a Caribbean getaway. It’s hard to believe you’re still in Florida. Sanibel has been recognized as one of the Best Places to Visit in 2026 by Travel + Leisure and featured in The New York Times’ “52 Places to Go in 2026,” thanks to its natural beauty, peaceful atmosphere, and world-famous shelling beaches.

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.

Island Retreat Steps from the Beach! 2 BR / 2 BA

Welcome to Sol Mate Too – A Private Island Retreat Steps from the Beach! 🌴🏖️ Sol Mate Too is a beautifully modern second-story vacation home, perched among the treetops just steps from the Gulf of Mexico. With 2 bedrooms, 2 baths, and a spacious open-concept living area, this bright and airy retreat offers a unique blend of seclusion and convenience.

Rare walkout condo on Sanibel beach

READY FOR YOUR SANIBEL VACATION! Everything you need in this recently updated, comfortable 2 bedroom, 2 bath condo on beautiful Sanibel Island, Breakers West Unit A-6. Rare ground floor location; private walk-out patio leaves you just steps to the pool and less than a 2 minute walk to the world famous Sanibel beach on the Gulf of Mexico.

Beach Paradise: Oceanfront, Sleeps 10, Pool, Games

Discover the allure of Beach Paradise, a brand-new listing boasting unparalleled luxury. This recently furnished 4-bedroom rental property rests directly on the pristine Gulf of Mexico shores, nestled amidst lush tropical surroundings adorned with swaying coconut palms and pristine white sands adorned with exquisite seashells.