180 properties available

Located in Captiva, Florida, United States. Private Waterfront Resort - Complimentary Concierge to Plan Ultimate Vacation Inspired by the Greek Islands+celebrating our 10th AnniversaryView the beautifully decorated villa with 11 bedrooms, 12 bathrooms, 4 waterfront acres. New Pickleball Court!!Family Vacations, Corporate Retreats, Exclusive WeddingsWelcome to Sea Oats Luxury Estate, your exclusive retreat on the enchanting shores of Captiva Island. As a distinguished member of the esteemed Drip Castle Estate Collection, Sea Oats invites you to savor the heartwarming embrace of family gatherings and the laid-back allure of a waterfront sanctuary.Experience the essence of Sea Oats Luxury Estate on Captiva Island—a day unfolding in perfect rhythm with the island's charm. Begin with a family breakfast in the chef's kitchen, fostering connections amidst shared laughter. Bask in the sun by the oversized pool or embark on a paddleboarding adventure along Buck’s Key, a wildlife preserve. Wellness enthusiasts can enjoy our full gym with

Located in Captiva, Florida, United States. ON beach top two floors two kings one queen two sleeper sofa south seas resort Feel free to ask about discounts. $250 fine to your security if you keep the lights on the patio and also if curtains are not drawn from9pm to 7am due to turtle season.access to three condo poolsThere are new courts you also have access to Great biking on captiva two bedrooms with king bedstwo full bathrooms tub shower comboLoft with queen bedTwo king beds are memory foamall new bedding and lampsuse of three condo poolstwo sleeper sofas in the living room brand new all furniture in the unit as of 2024granite in kitchen and bathroomsunit is on the top two floors of the resort with commanding views of the water (gulf) Balcony is screened in Kitchen is supplied for cookingSmart TV's no cable Elevators are functional but I make no guarantees as if they will be working during your stay due to the fact they are mechanical items I will not do refunds if elevator decides not to work during your stay Make sure to get

Located in Captiva, Florida, United States. ON beach south seas resort king bed three twins top two floors sleeper sofa $250 fine to your security if you keep the lights on the patio and also if curtains are not drawn from9pm to 7am due to turtle season.This is a two bedroom two bath beach villa in south seas resort. The top two floors in an elevator building unit 2433Renovated and very nice this has the BEST views since it occupies the top two floors of the condo complex. one king bedroom two twins in the second bedroomThere is a twin bed in the loft and a sofa sleeper in the living room. very quiet unit since it is on the top two floors of the resort.beach items available to include beach chairs, beach towels and cooler. An umbrella MAY be available I do not guarantee it since it gets broken by quests frequently and does not get reported as damaged but I check them every time I am there. I do require a rental agreement be signedGolf Carts can be rented with a local providerI no longer guarantee the use of umbrellas in my

Located in Captiva, Florida, United States. 2 BR South Seas Island Resort on the Beach Our 2 Bedroom apartment unit located in a prime location within the exclusive 5 star South Seas Island Resort faces directly on the beach and gulf. The unit features 2 bedrooms and sleeps 6, including a King bed in the Master overlooking the gulf that has private en-suite bathroom with shower, a 2nd bedroom with 2 twin beds has private bathroom with tub. There is a full kitchen, dining area, living room with queen size pull-out sofa and a full screened-in porch with dining table and chairs overlooking the beach and spectacular gulf sunsets. The unit has full access to plantation beach club amenities including pool, bbq, tennis and laundry room. General amenities of South Seas Resort including golf and other pools, tennis and restaurants are available for an additional resort fee. There is air conditioning, wifi and 3 TV's including 2 bedrooms and living room. The unit is on the Lower Level (one flight of stairs above the unit's private parki

Located in Captiva, Florida, United States. South Seas Beach Villa 2424 -Captiva Island gulf front beach vacation rental Beach Villa 2424 is a vacation rental condo on Captiva Island within the exclusive South Seas Resort! If you love spectacular views, sunsets to match, and being within walking distance to the quaint village shops, restaurants, and fun of Captiva Island, then Beach Villa 2424 is perfect for you! Prepare to be whisked away to a tropical paradise like no other at Villa 2424, the epitome of luxury and relaxation. Nestled amidst pristine white sands and crystal-clear waters, this vacation haven offers breathtaking views and unrivaled amenities. Every moment spent in Beach Villa 2424 is like a dream come true, making it the ultimate destination for your well-deserved escape. This 2 bedroom, 2 bath Gulf-front retreat is beautifully appointed with newer furnishings and mattresses and is fully stocked with everything you need to make your stay more enjoyable. Have meals on the spacious lanai as the sun sets over the h

Located in Captiva, Florida, United States. RESTORED TO TIP-TOP SHAPE AND ACCEPTING RESERVATIONS FOR 2024! A Tuscan villa located in the heart of Captiva Village, with all the amenities to accommodate a multi-generation family vacation.Just steps away from the blue water beaches and in the heart of Captiva Village is this luxury home featuring 5 bedrooms, 5 ensuite bathrooms, 4 balconies, a heated pool, infinity hot tub, gourmet kitchen, laundry room, large dining table, outdoor eating areas, outdoor grilling area and a covered bar by the pool. This home also has a elevator if anyone in your party needs assistance with the stairs.Captiva Attitudes has 4 king beds and 3 queen beds. Your rental includes all linens, towels, beach towels, beach chairs, beach umbrellas and a beach cart ... for no additional fee!The gourmet kitchen features a 6 burner gas stove, granite countertops, 2 large refrigerators, dishwasher, wall oven and two sinks. We also provide a Keurig coffee maker, microwave and other kitchen essentials.With over 4,0

Located in Captiva, Florida, United States. ROYAL PALM HOUSE - Luxury Style 3 Bedroom Home On Captiva With Private Pool INTRODUCING THE ROYAL PALM HOUSE*BOOK AND STAY JULY 1ST-OCTOBER 31ST, 2023 AND RECEIVE A FREE GOLF CART RENTAL WITH YOUR STAY! THIS $500 VALUE ONLY LASTS WHILE CARTS ARE STILL AVAILABLE!*A Note To Our Guests:With each new sunrise, we’re one day closer to normal on the islands of Sanibel and Captiva. We’re working diligently with our owners to reopen their vacation rentals as quickly and safely as possible. Please be aware that clean up and construction work will continue throughout the islands due to Hurricane Ian.HOME FEATURESThis three-bedroom home is situated on the Silver Palms Estate and is tucked away on the Roosevelt Channel, giving you a peaceful and relaxing feel and is every fisherman's dream with a private dock, private heated pool and full resort access to Tween Waters Island Resort and Spa, only 0.5 miles away! This home can sleep up to nine guests and is dog friendly with owner approval (additiona

Located in Captiva, Florida, United States. Villa Del Mar - The ultimate vacation home now reduced for 2024! Beach, Shops, Restaurants, Music, Boat Cruises and Galleries all WALKING DISTANCE from Villa Del Mar. Experience the ultimate vacation home in this beautiful five bedroom, media room, game room and heated pool!Villa Del Mar (Formerly known as Breathless) is a stunning five-bedroom home on the best street on Captiva Island! Located five houses from the world-famous stunning white beaches of Captiva Island but also in the heart of Captiva Village. This home and location are the best of both worlds! Hidden behind the double wood doors is an amazing courtyard with a large, heated pool, a hot tub, pool games, and multiple lounge chairs.Walking into the home on this first level means walking into a large game room with a ping pong table, flat-screened TV, and foosball. The theater room with large pit couch that can be made into an extra queen bed is also on this level as well as a large bedroom with two queen beds, flat screen

Located in Captiva, Florida, United States. Lollipop, the perfect Captiva Home **Lollipop is considered a value property which means great location, good interior but some worn fixtures and some worn exterior**Lollipop, the perfect Captiva vacation home. Central to Captiva village this three bedroom three and ½ bath pool home offers the perfect escape for a relaxing vacation. There are so many great features to this home, cathedral ceilings, screened in porch, updated modern kitchen, pool and spa and multiple decks. A short three minute stroll down sandy Laika Lane and you will be on the world renowned beaches of Captiva. The master suite features a comfortable king size bed and large shower in the master bathroom. The first large guest room features ample space a comfortable queen bed and bathroom in the hallway. The second guest room has a double bed and ample closet space. A day bed off of the living-room with a trundle is a comfortable space for your guests. The third full bathroom is located off of the dining area o

Located in Captiva, Florida, United States. 150 yards to the beach. Waterfall resort style pool, private theater and more Welcome to "Stayawiles," your newly refreshed dream vacation rental! This luxurious 6-bedroom home is a haven for families in search of the ultimate beach retreat. Positioned mere steps from the sandy shoreline, you'll relish the serene ambiance of the waves and the easy beach access. This expansive abode, named "Stayawiles", features two distinct living areas, providing ample room for both relaxation and entertainment. The residence boasts not one, but two master suites, ensuring maximum privacy and comfort for all. Enjoy ultimate relaxation with your very own private pool, inviting you to take refreshing dips or soak up the sun. For indoor amusement, a pool table awaits friendly competitions, and a cutting-edge theatre room offers a premier cinematic experience. Your family's perfect vacation awaits—book now to secure this remarkable rental at "Stayawiles"!Do you remember Lifestyles of the Rich and Famous?

Located in Captiva, Florida, United States. Coco Mango by AvantStay | Chic and Private Captiva Escape Sweeten up your Sunshine State experience at Coco Mango — a charming retreat in Captiva. This bright, welcoming home features a gorgeous entertainer's backyard, perfect for hosting a group. Spend your days lounging poolside, surrounded by foliage, as the waterfall from the stone hot tub fills the air with ambient sound. The shaded deck features a lounge area, grill, and comfortable tables, while heading up the spiral staircase will lead you to the upper balcony with views toward the shore.Inside, Coco Mango has a clean, elegant feel and contemporary warmth. The main living room, downstairs rec room, and upper lounge area give your group plenty of space to spread out while keeping everyone entertained. If you're feeling competitive, a pool table and shuffleboard table are both available. Whip up a snack in the spacious kitchen, take a soak in the primary ensuite's luxurious corner tub, or head to nearby Cape Coral and Fort Myers

Located in Captiva, Florida, United States. Beachfront Bliss: MANGROVE MANOR- Elevator, Private Pool and Spa, Boat Dock Welcome to Mangrove Manor, your ultimate beachfront getaway! This stunning 5,886 sqft, 5-bedroom, 5-bathroom house is directly on the Pine Island Sound beach for stunning sunrise and sunset views!Mangrove Manor towers over North Captiva Island providing nearly 360° views on each level!With a private pool and spa, you can relax and soak up the sun while enjoying the breathtaking ocean views. Take a stroll out front to your own private beach STEPS AWAY from the front door!The house also features a private boat dock, perfect for exploring the waters at your leisure. Sit on the boat dock and admire the work of the osprey nest on its perch or watch the dolphins swimming around the docks playing!Inside, you'll find two bars for entertaining, a gourmet kitchen with a gas range, and enough space to comfortably sleep 19 people. Did we mention it has an elevator?!Whether it's a family vacation or a friend gathering, Mang

Located in Captiva, Florida, United States. The Salty Conch - Luxury Just Steps To The Beach with Private Pool Book your stay at the beautiful, new to the rental market, island house, just a short golf cart ride to the beach!The Salty Conch is an exquisite home for comfortable living and on a private site located close to the gulf beaches on a quiet sandy lane. Surrounded by a tropical landscape with circular patio and a private, heated pool. Screened-in outdoor living space with TV, games, dining, and sitting areas. A lovely two-story foyer greets you on the first level, plus two King bedroom suites and an additional Queen. A loft room with a Full bed and fantastic Gulf views surrounded by sliding glass doors that lead to the top lookout deck with panoramic views of the island. The luxurious, fully equipped kitchen with living room and dining to enjoy a full family experience. The Salty Conch is the place to Make Memories that last a Life Time!When you book this house, you and your family have access to the North Captiva Island

Located in Captiva, Florida, United States. Captiva Village Home This 5 bedroom, 4 bath luxurious home is located in the heart of Captiva Village with private beach access just 450 feet away. With its prime location, you are just steps away from restaurants, live music, marinas and shopping. This home is light and bright with a spacious floor plan and high ceilings. The home has been completely updated and features a fully equipped gourmet kitchen and a beautiful dining area opening up to a screened lanai. The outside of the home has been beautifully landscaped and includes a screened in heated pool, a putting green, and several covered sitting areas. There is also a roof top sun deck to enjoy during the day or stargaze in the evening.

Located in Captiva, Florida, United States. Special summer pricing! Luxury Beach House, Private Pool, just steps to beach Do not miss the opportunity to enjoy a relaxing family friendly summer getaway at one of North Captiva's best properties offering Summer Specials to welcome guests back to our beautiful island paradise! After an 18 month long top to bottom renovation, we are thrilled to welcome back guests to enjoy the luxury finishes and amenities of La Casa Del Sol comfortably accommodating up to 12 guests.The beach is calling so there's no better place to soak up the sun and escape the crowds than this beautiful beach home! Located on the private island of North Captiva, La Casa Del Sol (the house of the sun) is a luxury 4 bedroom beach home that boasts stunning ocean views just steps from the beach. This private pool home offers a tranquil getaway for up to 12 of your family and friends, with everything you need to relax & entertain in style. Designed with a relaxed coastal feel, this home is sure to delight those who

Located in Captiva, Florida, United States. Drip Castle Estates Captiva Island - 20 Bedroom Estate Rentals for Large Groups! Welcome to Captiva Island's Ultimate Paradise! 🌴Are you ready for a double dose of tropical bliss? The Drip Castle Estate Collection is thrilled to present the spectacular Sea Oats Luxury Estate and the magnificent Sea Palms Estate, your passport to paradise on Captiva Island, Florida! 🌞🏡 Sea Oats Luxury Estate: 🏡Picture yourself in an opulent seaside sanctuary, where luxury and relaxation unite in perfect harmony. The Sea Oats Luxury Estate is your ticket to a waterfront haven like no other. Featuring 11 bedrooms, this spacious property is designed to accommodate large groups and events. Inside, you'll find every modern amenity, and outside, the shimmering Gulf of Mexico will be your backdrop. Enjoy morning coffee on your private veranda, and finish the day with a mesmerizing sunset stroll on the pristine beach right at your doorstep.🌴 Sea Palms Estate: 🌴Welcome to your very own tropical paradise at the S

Located in Captiva, Florida, United States. Quiet, clean townhouse. Relaxing winner. Harbor view, short Gulf walk… Nice relaxing townhome…. Simple, white, clean…. A few steps from the harbors edge. Great place to escape from work, or great place to escape the mainland and work…..kayak right from nearby launch, or walk 1200’ to Gulf of Mexico beaches. Dockage of boat included and nice golf cart. Use of Safety Harbor Club heated pool and new tennis courts included. Boat slip 35yards from townhouse. New grill, fully stocked kitchen. 2.5 bedrooms.

Located in Captiva, Florida, United States. Linesider Hideaway Beach House - North Captiva Island Welcome to North Captiva Island and our home Linesider Hideaway. North Captiva is a barrier island to the west of the mainland Pine Island and is only accessible by private boat, island ferry or private plane. The seclusion of this island are what make it truly unique, close enough for modern amenities, but far enough for a nice break and slow down. Whether you are coming to the island to spend more quality time with the family or coming with a group of friends to enjoy the year round fishing opportunities close by, North Captiva has something for everyone.The island currently has two functioning restaurants, Mangos Pool Bar and OTW (Over the Water restaurant), both which are very close to our home. Next to Mangos is a small island store with some bare essentials and Boats n Fun where you can rent kayaks, golf carts, fishing or sight seeing charters.This is a new custom 3 bedroom 2 bathroom home in Safety Harbor Club on North Captiv

Located in Captiva, Florida, United States. TARPON COVE - Coastal Luxury 2 Bedroom 2 Bathroom Island Home ***Post Hurricane Ian Update 6/1/23***Thank you for your interest in Tarpon Cove.We’re happy to report that the island is recovering really well and coming back to life. Our repairs are finished and we are happy and excited to see new and familiar faces come and visit Tarpon Cove! Book your next vacation now!Thank you,Andrey & Lana Gera****************************Follow and get to know us on Facebook and Instagram! Search: VisitTarponCovewww.visittarponcove.comLana 440-308-7813 / Andrey: 216-570-7269Come and stay at Tarpon Cove and experience true paradise living in a luxury 2 bedrooms 2.5 bath home located on North Captiva Island!!(1) 4 person Golf Cart IncludedBEDROOMSMake yourself at home at Tarpon Cove with two bedrooms located on the first floor. The master bedroom has a king-size bed with a memory foam mattress. The spare bedroom has two queen size beds. Both bedrooms have access to a screened-in deck overlooking beaut

Located in Captiva, Florida, United States. Island Oasis/Hidden Beach House-Private pool This traditional, Florida-style island cottage is situated less than 200 yards down a private path to the Gulf of Mexico. This home has only one elevated, single-level, floor plan providing ease of access and family-friendly living. It is designed to provide the utmost comfort while capturing the scenic beauty around it.Features include: Outdoor living environment includes a heated pool with wrap around wooden deck, covered outdoor bar, pool table, barbecue and eating area. The relaxing and stylish interior retreat has a spacious private master suite with study/sitting area and master bath, along with two additional bedrooms in a split floor plan, and a second large bath. Sleeps six with one king, one queen, and two twin beds. A convenient utility room with washer and dryer adjoins the kitchen.The village of Upper Captiva: The village of Upper Captiva sits on the northern tip of North Captiva Island, a secluded tropical island in Southwes

Located in Captiva, Florida, United States. Manatee Haven: Screened-in Pool, Spa and Elevator! 2 Golf Carts Summary:Manatee Haven has been fully rebuilt and renovated post Hurricane Ian. The house is spectacular. Manatee Haven Beach House is located on the exclusive barrier island of North Captiva Island, Manatee Haven is an upscale, non-smoking,  beach-view home that offers four bedrooms and three and a half bathrooms with an elevator to all three levels. It is professionally decorated, has a swimming pool and hot tub located under a 3,200 sq. foot private screened-in pool deck that includes a full outdoor kitchen.The Space:Our home offers every amenity for our guests, including paid access to the private North Captiva Island Club facilities and a private beach access just 500 feet away.  Your rental includes two golf carts.  We do not allow pets in our home.GROUND LEVELYou'll think you walked into heaven as you enter Manatee Haven.  The lower level pool deck is where most spend their time when not out at the beach or hiking

Located in Captiva, Florida, United States. Spectacular Sunsets. Private multilevel designer home with heated pool and spa Multilevel Designer Home with plenty of room for family. Multiple living areas and plenty of outside areas to enjoy. The home has amazing Sunrise and Sunset views. Walk or take the golf cart to the beaches or relax in the private heated pool with an overflow spa. In addition, expanded lot with plenty of outdoor space to enjoy!! No Plans III is a luxury 2700 square-foot beach house with a private pool and 2 golf carts!!!Enjoy No Plans III, an architectural delight providing a standard of living second to none. This lovely beach-view home has no shortage of quality and award-winning elegance. The designers of this beautiful home intentionally named this model, The Deck House, providing numerous decks off every level. The combination of interior elegance and exterior delight blend together seamlessly as it was always meant to beAs you enter into the No Plan

Located in Captiva, Florida, United States. The MAINE DECK - BRAND NEW DESIGNER HOME WITH PRIVATE POOL AND 2 GOLF CARTS BRAND NEW HOME - SCHEDULED FOR COMPLETION 02/28/2022Welcome to the Maine Deck! Our beautiful dream home is brand new with construction completed in February of 2022. On the first floor our home features four spacious bedrooms - 2 kings with en suite baths, and a bunk room that sleeps six with a hall bath. A fourth bed (queen) and bath is located on the second floor. This house comfortably sleeps 12.From the second floor enjoy views of the gulf while cooking in our gourmet Kitchen. You can dine in at our oversized kitchen counter or in the full size dining room. If fresh air is what you desire you can enjoy the full length screened porch for dining or just relaxing and watching the sunset. The kitchen has a Reverse Osmosis water system so no need to bring cases of bottled water - it’s crystal clear!But for the real views check out the bonus room on the third floor, complete with two decks facing east and

Located in Captiva, Florida, United States. Airstrip Ocean Oasis: Pool, Hot Tub, Views & Golf Cart Welcome to Tortuga Sunset – Your Caribbean Escape on North Captiva Island!Transport yourself to paradise at Tortuga Sunset, where serene ambiance and natural beauty will whisk you away to the Caribbean without leaving the comforts of North Captiva Island. Nestled within this barrier island haven, our vacation home offers a tranquil retreat from the everyday hustle and bustle, inviting you to unwind and create cherished memories.Built in 2021: Enjoy a spacious 2350 sq ft oasis with cathedral ceilings and 8 ft doorways.Accommodations: Two king master suites with ensuite bathrooms. One king bedroom with a twin bunk bed and an attached bathroom. Open room with a queen Murphy bed.Modern Amenities: High-speed internet. Private outdoor heated pool and spa. Screened-in back porch. 6-person golf cart (option to rent an additional 4-person golf cart). Island Club North Captiva Membership available for a nominal fee (access to kayaks,