Vacation Home Rentals By Owner In Captiva, FL

Rated 9.8/10 by 182 guests — one of the highest-rated beachfront rentals on North Captiva Island.brbrTHE SPACEbrbrRainbow's End sits on a rare private beachfront point at the northern tip of North Captiva Island — a spot so secluded it has its own name: Rum Point. With the turquoise Gulf of Mexico just 10 steps from your door and 4 acres of untouched tropical land behind you, this is the most private and peaceful beachfront on the island. There are no neighbors in your sightline. No road noise. Just the sound of waves, the rustle of palm fronds, and dolphins passing by most mornings.brbrThe home sleeps 7 comfortably across 2 bedrooms, with a full kitchen, washer/dryer, free WiFi, and air conditioning. Every room has been maintained to the same standard our guests have come to expect — and come back for.brbrTHE BEACHbrbrStep off the back deck and you are in the Gulf of Mexico. No walk down the street, no public beach access to share — just your private stretch of pristine white sand and warm, clear water, whenever you want it. The western exposure at Rum Point delivers what guests consistently call the best sunsets on the island: the sky turns every shade of orange and pink right in front of your dinner table.brbrWatch dolphins swim along the shoreline from the porch — this happens on most days and never gets old.brbrYOUR GOLF CART IS INCLUDEDbrbrNorth Captiva has no cars — just lush sandy trails and golf carts. Yours is waiting at the dock when you arrive. A relaxed 5-minute ride brings you straight to Rainbow's End, and from there the whole island is yours to explore at your own pace. Use it to find a quiet beach on the other side of the island, grab a drink at the pool bar, or simply cruise the trails as the sun goes down.brbrTHE ISLANDbrbrNorth Captiva is a true offshore island — accessible only by boat or small plane. No cars, no chain hotels, no traffic lights. Around 300 homeowners. Miles of untouched beach. Over 600 acres of Federal Wildlife Preserve with hiking trails, exotic birds, and complete solitude whenever you want it.brbrWhen you do want company, the island delivers:brbrPool bar and grillbrMarina restaurantbrGuided fishing and boating toursbrBoat rentals and kayak toursbrSmall convenience storebrGrocery delivery to the dockbrDaily island-hopping and dolphin-watching tour boatsbrbrGETTING HEREbrbrFerries depart from Pine Island throughout the day — it's a 20-minute crossing. You can also fly in by small plane. Once you land, your golf cart is waiting. First-time visitors often say the ferry ride itself feels like the start of something different. They're right.brbrWe recommend stocking up on groceries before you board, or pre-ordering a grocery delivery to arrive when you do. The island has a small market, but part of the magic is having everything you need and nowhere you have to be.brbrGOOD TO KNOWbrbrSleeps 7 · 2 bedrooms · 2+ bathrooms · 1,200 sq ftbrGolf cart included for the duration of your staybrPrivate beachfront — no public access nearbybrFull kitchen, free WiFi, A/C, washer and dryerbrFerry departs from Pine Island (approx. 20 min)brPeak season: January through April — book earlybrbrONE LAST THINGbrbrThe most common thing our guests say when they leave That the week ended too soon. We hear it every time. Book early — Rainbows End fills up fast, and once you've been, you'll understand why guests keep coming back year after year.

Private BEACHFRONT Point - Dolphins, Sunsets & Golf Cart Included/North Captiva!

Captiva, Florida, United States

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Bath

Sleeps

$936.83

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!brbrDo you remember Lifestyles of the Rich and Famous Stay for a week or longer at Stay A-Wiles on Captiva Island and you will feel like a celebrity. Our home has recently been refreshed and decked out to the fullest. The home has over 4,000 sq ft of space to accommodate up to 14 guests. Downstairs is a private theatre featuring leather chairs with retracting screen, billiards table, wet bar and walk right out to the resort style pool area complete with a hot tub, waterfall feature and slide. Downstairs has the theater as well as a bedroom with 2 full size beds and full bathroom. The entire pool area is screened in for privacy and comfort. The main level features a chef's style kitchen with high end appliances, sitting room as well as 3 bedrooms/3.5 bathrooms. Upstairs are two spacious primary suites with king sized beds and en-suite bathrooms. You are situated in the heart of Captiva Village which not only puts you within 150 yards of the sand, but also a short walk to shops and restaurants. Want to relax and read a book while on vacation .... the quaint Captiva Library is just down the lane. Book your stay today and experience a vacation like you've never had before!brbr**Rent our new 6 person golf cart to easily get around the Village area. Inquire with Dream Vacations or add to your reservation during the check-out process** brbr*Important Note: This rental does not include beach chairs or umbrellas. Instead, we’ve partnered with VayKLife to provide you with a credit toward beach essentials like chairs, umbrellas, coolers, wagons, and more—so you can pack light and still enjoy everything you need for a perfect day at the beach. While some of our homes may have beach gear on-site, availability varies, and we cannot guarantee specific items will be provided. With VayKLife, you get to choose exactly what you need, and they’ll deliver it right to your door for added convenience. Your booking confirmation includes a link to VayKLife’s site, where you can browse their full selection and easily redeem your credit. It’s just one of the ways we help make your stay as seamless and enjoyable as possible.

150 yards to the beach. Waterfall resort style pool, private theater and more

Captiva, Florida, United States

Bed

Bath

Sleeps

$683.38

Tortuga Paradise introduces Tortuga SunsetbrCheck out our online reviewsbrbrThe Space – Designed for Connection & Comfortbr2,350 sq ft ranch with soaring ceilingsbrbrSleeping (Sleeps 10)br• 2 King master suites with ensuitesbr• King + twin bunks, attached bathbr• Bonus Queen Murphy bedbrbrIndoor LivingbrOpen layout, gourmet kitchen, 5 smart TVs, Starlink WiFibrbr Outdoor Livingbr• Heated saltwater pool + spabr• Screened sunset porch (ocean views)br• Outdoor kitchen, fire pit, lounge + ping pongbrbr✈️ Island CharmbrNear small airstrip—occasional planes, no runway access

Tortuga Sunset| Ocean Views/Private Pool/Golf Cart

Captiva, Florida, United States

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Bath

Sleeps

$515.29

Secluded island escape with a heated pool, volleyball court, pingpong, outdoor kitchen & golf cart. Sleeps 10 with 2 king suites + bunkroom — perfect for families & groups, anglers or multi-generational.brbrWe've recently added pingpong outside by the pool, 2 paddle boards to strap to golf cart roof and take to whichever beach your heart desires. AND built a private volleyball court on our side lot, to entertain your kids/teens or even get a good adult game going! The Pool is warm, the beaches are beautiful and our new landscape and outdoor lighting is sure to give you all the paradise vibes. Enjoy the world class fishing Captiva offers, the stunning beaches, or boot around the car-less island in a golf cart. Otherwise, relax by your private pool, grab a cold one and fire up the grill. The space:brSplit floor plan, perfectly set up for 2 families, with an ensuite master bedroom (king) on one side of the house, a second ensuite bedroom (king) on the opposite side of the house, with a third bunk room (2 queens and 2 twins) for all the kids! The house has an open floor plan with plenty of space for games or just relaxing. The TV in the great room is internet connected and can be used with most streaming services; just login! The kitchen is fully equipped with a blender, coffee maker, and a propane grillbroutside. Plenty of games for kids, including monopoly,brEnjoy relaxing mornings having coffee and breakfast on the lanai overlooking your private heated pool.

Paddle Boards-Heated Pool-Golf Cart-Volleyball Court-HOT Outdoor Shower-Bunkroom

Captiva, Florida, United States

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Bath

Sleeps

$1640.24

NEW TO THE RENTAL MARKET — Be one of the first to experience Captiva’s finest beachfront living! brbrWake up to breathtaking 180-degree views of both the Gulf of Mexico and the Bay in this extraordinary beachfront home, ideally positioned between two spectacular shorelines. Designed with relaxed coastal elegance in mind, this spacious and luxurious retreat offers seamless indoor-outdoor living—perfect for entertaining, unwinding, and creating unforgettable memories. brbrAn open-concept layout with a thoughtful split floor plan offers both privacy and connection. Natural light pours through expansive windows, showcasing sweeping water views from nearly every room.brbrOutdoor Living Highlights:brStep outside to enjoy multiple decks, a screened lanai, a large fenced backyard with pavers, and a private pool and spa—all nestled in lush tropical landscaping. For those who enjoy time on the water, the property includes access to a shared dock (ideal for fishing only).brbrBedroom Layout:brMain Floor Gulf-Front Guest Suite:brEnjoy a beautiful Gulf view in this serene guest room with a queen bed and direct access to the screened lanai. Wake up to stunning Gulf views and the peaceful rhythms of coastal life.brbrMain Floor Guest Suite with Pool and Bay Views:brThis inviting queen bedroom offers tranquil vistas of the pool and Bay, making it a restful retreat for guests.brbrTop Floor Master Suite:brThe ultimate sanctuary—this spacious suite features a king bed, panoramic Gulf views, a luxurious spa-style bath, walk-in closet, and front-row seats to dolphins by day and stars by night.brbrEntertainment Den:brEnjoy your favorite shows and movies with the large flat-screen television.brbrLower-Level Family Suite:brIdeal for families or larger groups, this level includes a full living area, a bedroom with a king bed and two twin beds, a full bathroom, and direct access to the pool and beach.brbrAdditional Features:brPrivate pool and spabrGourmet kitchen with Gulf views, stone countertops, and access to an alfresco dining deckbrAdditional ice maker for guest convenience—perfect for beach days and entertainingbrMultiple outdoor spaces for relaxing or entertainingbrGalvalume roof, composite decking, and impact-rated windows and doors for peace of mindbrOne Bay garage access available for loading/unloading only (no vehicle parking)brSecurity camera monitoring of outdoor areas onlybrDock access is for fishing use onlybrbrLocation Perks:brCentrally located near Tween Waters and Captiva Village—walk to dining, shopping, and island activities. Whether you're watching the sunset from one of the many decks, swimming under the sun, or enjoying an evening breeze, this home offers the ultimate in coastal comfort and luxury living.

Unparalleled Gulf-to-Bay Living - Luxury Beachfront Retreat-Captiva Island

Captiva, Florida, United States

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$708.06

Summary:brbrIf you're looking for a tropical vacation home that's perfect for a large family, our stunning Captiva Island Pink House Villa should not be missed. This private four-bedroom home, located on the Roosevelt Channel, boasts its own dock and pool. The quintessential Florida vibe is impossible to ignore.brbrbrbrThe Space:brbr**Beach Access Information Listed Below** brbrbrbrStart your day by enjoying a cup of coffee from one of the many balconies. For some afternoon activity, grab a fishing pole or take a kayak ride. If you are lucky, you may even see a manatee swimming in the Pine Island Sound Aquatic Preserve. Whether the purpose of your trip is a family vacation or a couples retreat, the Pink House will not disappoint.brbr brbrThe home is nearly 4,000 square feet and can comfortably accommodate up to 10 people. The home has a wonderfully stocked kitchen with modern appliances that will make you feel right at home and tastefully installed modern technology, including large flat screen TV's. The rental includes quality linens, towels, shampoo, conditioner, toiletries, and more!brbrbrbr**Please note, the photos displayed are pre hurricane Ian. The only thing that has changed is that the second-floor master balcony is currently unavailable, and the landscaping on the property has not fully returned to its former lush state, but apart from that everything is available as displayed.brbrbrbrRelax. Unwind. Enjoy. brbrbrbrbrbr**BEACH ACCESS INFORMATION: We are located on the canal side of the island and do not have private beach access. The public beach is easily accessible and just half a mile down the road.brbrbrbr**The pool can be heated for a fee of $50/night.brbr**A high chair and pack and play can be made available for no additional fee. Please request prior to arrival. brbr**The bunk beds are full over full bed sizes.brbrbrbrGuest Access:brbrOur guest relations team will send over a door access code before your arrival.

Waterfront Pink House with Private Dock & Pool!

Captiva, Florida, United States

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Bath

Sleeps

$363.85

Welcome to your dream Captiva getaway at our RARE Two-Story Beach Villa with Direct Gulf Views!brbrDiscover the ultimate island escape in this stunning 3-bedroom, 3-bathroom villa, perfectly situated on a corner lot for abundant natural light and enhanced privacy. Step inside and let the open-concept living, dining, and kitchen areas envelop you in comfort – ideal for entertaining or simply unwinding after a sun-kissed day on the sand.brbrImagine savoring a refreshing drink as you listen to the calm rhythm of the waves, all while witnessing an incredible Captiva sunset paint the sky from the luxury of your living room or private patio. It's the perfect backdrop for unforgettable vacation memories.brbrThis spacious villa offers flexible living across two levels. On the main floor, you'll find the serene primary bedroom with its own en-suite bathroom, plus a convenient guest bedroom and a separate full bathroom. Ascend the stairs to discover an additional private bedroom, complete with its own en-suite bathroom, ensuring plenty of space and comfort for family, friends, and guests alike.brbrAs part of the charming Gulf Beach Villas community, your stay includes access to fantastic amenities. Take a dip in the sparkling community pool, enjoy a friendly match on the tennis or pickleball courts, or host a casual BBQ at the grilling stations. Best of all, you're just steps away from the soft, sandy beaches of the Gulf of Mexico!brbrThe prime location means you're also just a short stroll from the vibrant Village of Captiva, where you can explore charming retail shops, grab your morning coffee at Starbucks, or indulge in delicious dining experiences.brbrThis villa offers the perfect blend of coastal living and convenience, promising an unforgettable Captiva vacation. Book your stay today and start making incredible memories!brbrImportant NotesbrbrPrivate ManagementbrThis condo is privately managed and not affiliated with the resort. Guests do not have access to resort amenities. A paid laundry facility is available on the ground level.brbrBeach GearbrBeach chairs and umbrellas are not included. Instead, your stay includes a VayKLife credit for beach essentials such as chairs, umbrellas, coolers, wagons, and more. Delivery is included. On-site availability cannot be guaranteed. Your booking confirmation includes a link to redeem your credit.brbrConstruction & MaintenancebrCurrently, there are no ongoing repairs or construction within the Resort. Should any occur during your stay, refunds will not be issued for disruptions caused by maintenance or repairs beyond our control.brbrStorm ImpactsbrDue to Hurricanes Helene and Milton, access to some amenities may be limited during your stay.brbrPool ClosurebrThe pool will be closed starting January 5, 2026. This closure is expected to last one (1) month. The other two pools at the Beach Villas will remain open and available to guests. One is in front of the 2300 building, and the other is in front of the 2500 building brbr

Beach Villa 2121: Your Exclusive Two-Story Beach Villa with Direct Gulf Views

Captiva, Florida, United States

Bed

Bath

8

Sleeps

$2733.16

Panoramic views of the Gulf and beautiful Captiva sunsets welcome you to this island escape. With an open living area and spacious floor plan decorated in soothing grays, this three bedroom, three bathroom, contemporary, beachfront villa is the perfect place to unwind. A polished, fully equipped gourmet kitchen with island opens onto a rustic dining table and beautifully furnished living area complete with a large flat panel television and cozy sectional. Slide open the large glass doors and step outside to soak in views of tall beach grass and stunning ocean view. The main floor master bedroom features a comfortable king bed, luxurious en-suite bath with walk-in shower, and Jack and Jill sinks. Just down the hall is a guest bedroom furnished with two twin beds, wall-mounted flat screen TV, and modern touches. Located on the second floor is a third bedroom furnished with a queen bed, soft white bedding, and an airy loft area just outside the door that opens to a balcony that’s perfect for sky gazing. You’ll enjoy the many activities and amenities that South Seas Island Resort has to offer at this beautiful cottage that accommodates up to six guests. brbrCottage Includes:br1,500 square feetbr3 Bedroom / 3 BathbrDirectly on the beachbrSteps to the community poolbrShort golf cart ride to North Pointe amenitiesbrViews of the Gulf of MexicobrFully equipped kitchenbrLiving Room has views of the Gulf and flat panel TVbrKing size bed, flat panel TV, walk-in shower and closet in master bedroombrScreened lanai overlooking the Gulf of MexicobrSundeck located on the second levelbrIn unit washer / dryerbrOutdoor gas grillbr1 parking spacebrMaximum occupancy of 6br3 night minimum stay requirement brbrHousekeeping will be on departure only.brbrThis is an OFFICIAL LISTING in partnership with South Seas Island Resort and guests will receive use of the resort’s amenities and services that are included in the resort fee. If you rent from an unofficial listing that is not provided by the official South Seas Island Resort, please be aware that you will not have access to any of the facilities and services on property, including housekeeping or maintenance. brbrRESORT FEE: South Seas Island Resort will charge a nightly resort fee of $25.00, plus 11.5% tax for each guest 12 years and older. The resort fee is not included with the room rate, and will be collected when you arrive at the resort.brbrThe Resort Fee Includes:br• Daily trolley service throughout the Resortbr• Main resort pool, Kiddie Pool & Slide amenities (poolside towels & lounge chairs) br• Beach amenities (beach towels, chairs, & umbrellas)br• High-speed internet inside homes, villas & throughout the resortbr• Participation in special Resort activitiesbr• Free parkingbrbrCURRENT AMENITIES AND SERVICESbrWe were excited to begin accepting reservations for some of our Homes of Distinction and Villas this summer. Additional accommodations will continue to become available, increasing considerably this spring. You’ll have access to our two-and-a-half glorious miles of pristine white-sand beaches, where you can take in our famous sunsets, world-renowned shelling, and incredible natural wildlife. While we continue to make progress on our recovery and rebuilding efforts, select areas of the resort remain under construction and some amenities will be more limited or modified than you are accustomed to.brbrIn addition to our private beach set-up and event programming, guests have access to Starbucks, several restaurants on Andy Rosse Lane, and two new food trucks:brbrTACOS POOLSIDE:brTacos at the pool Sounds good to us. This summer, indulge in a fusion of flavors at the Island Tacos food truck. Choose from a variety of tacos, nachos, and quesadillas. Plus, enjoy a special treat at sunset with our Shrimp Ceviche Cocktail.brbrSHELL CITY BURGERS:brDiscover delicious bites at the Shell City Burgers food truck this summer. From smash patties to local-inspired crab cakes and grouper filet sandwiches, you can grab and go or enjoy beachside with our outdoor seating.brbrYACHT HARBOUR & MARINA:brTop marina facilities at two locations. Yacht Harbour & Marina and Bayside Marina, home of dockage, a launch, rentals, and charters. We have a full range of amenities and services for you and your crew. A friendly and helpful Dockmaster and staff.brbrCART RENTALSbrEmbark on an adventure of island exploration by taking the wheel of our new EZGO carts. With four- and six-passenger carts available, your journey awaits!brbrGUEST SAFETY & CONSTRUCTION NOTICEbrTo ensure the safety and well-being of our guests, please be aware the resort is currently undergoing significant construction and improvements to further restore and add new amenity spaces. During your stay, you may encounter heavy equipment moving along the roadways and association parking lots, and near private homes and villa drives. For those who are biking, walking, or jogging, please remain vigilant and aware of your surroundings.

Beachfront Contemporary Cottage- Open & Airy-Gulf Views! OFFICIAL RESORT LISTING

Captiva, Florida, United States

Bed

Bath

6

Sleeps

$2349.92

A large wrap-around deck and Bay views welcome guests to this beachside getaway. With an open floor plan, bright tropical colors, and a prime location just 100 yards from the beach, this four-bedroom, three-bath home is the perfect vacation retreat for family and friends. The living area features a relaxing sectional sofa, large flat-panel television, and sliding glass doors that open to a patio overlooking the private pool and hot tub. A fully equipped kitchen is located off the living area with all the conveniences including a breakfast bar with seating, flat-panel television, and an island prep area, while the dining area seats up to eight guests. The main-level master suite offers views of the pool and the beach and features a king bed and ensuite with walk-in shower. A second downstairs bedroom with views of the lush tropical surrounds offers a queen bed. Upstairs there are two additional island-inspired bedrooms, one with a queen bed and the second with two twin beds, both of which open onto a loft that provides the perfect space to relax or to sleep additional people on the queen sleeper sofa. You’ll be sure to enjoy the many activities and amenities that South Seas Island Resort has to offer from this home that accommodates up to 10 guests. brbrHome Includes:brPrivate pool & hot tubbr3,300 square feetbr4 Bedroom with loft / 3 BathbrLoft with queen size sleeper sofabrMaster Bedroom overlooking the poolbrOpen kitchen featuring breakfast bar seating and flat panel TVbrDining Room seats 8brLiving room opens to screened lanaibrLess than a minute walk to the beach on deeded beach access pathbrSpacious sundeckbrWasher and dryer (2)brOutdoor gas grillbr3 parking spacesbrMaximum occupancy of 10br5 night minimum stay requirement brbrThis is an OFFICIAL LISTING in partnership with South Seas Island Resort and guests will receive use of the resort’s amenities and services that are included in the resort fee. If you rent from an unofficial listing that is not provided by the official South Seas Island Resort, please be aware that you will not have access to any of the facilities and services on property, including housekeeping or maintenance. brbrRESORT FEE: South Seas Island Resort will charge a nightly resort fee of $25.00, plus 11.5% tax for each guest 13 years and older. The resort fee is not quoted with the room rate, and will be collected at check-in. brbrThe Resort Fee Includes:br• Tennis / Pickleball court fees *br• Daily trolley service throughout the Resortbr• Resort pool complex amenities (poolside towels and lounge chairs)br• Beach (South and Sunset Beach) amenities (beach towels, chairs, and umbrellas)br• Fitness center accessbr• Guest room high-speed internetbr• Participation in special Resort activitiesbr• Free parkingbr• Tesla and EV charging stationsbr* All play requires advanced reservations. Players must check in at the Pro Shop before playing. Instruction and equipment are not included in the resort fee. Tennis reservations may be booked 7 days in advance of play. brbrAt South Seas, our sanitation procedures are rooted in the CDC guidelines, and we are following guidance from public health authorities. We will not be able to offer any early check-in or late check-out requests until further notice, due to the time it takes to properly clean and sanitize the unit for the next guest arrival. Our enhanced measures include: brbrPartnering with industry experts, such as Ecolab®, to ensure we have training on hygiene and infection prevention. Ecolab, a global leader in hygiene and chemical products, is a trusted industry partner. Training hotel staff on cleaning and sanitizing procedures developed by AIMClean, our robust cleaning and sanitizing certificate program includes best practices from in-house and outside experts. brIncreasing frequency of cleaning and special sanitizing using EPA-approved products throughout all public areas of the hotel, meeting areas, guestrooms and work areas focusing on high-touch areas and hard surfaces. brbrMinimizing exposure to guests and staff by cleaning and sanitizing your accommodation prior to your arrival. brbrProviding food and beverage offerings in a grab & go format or touchless delivery; providing rigorous food and beverage staff training; adhering to local health department guidelines along with guidance from the CDC, such as the use of PPE and food safety. brbrPhysical distancing throughout all areas of the resort including in public areas, fitness center, lobby, pool, beach, and retail. Where available, we encourage all guests to utilize touchless service. brbrOn behalf of the South Seas Family, we want you to know that when you are ready to visit, we are ready to welcome you completely prepared to provide a safe and enjoyable South Seas experience. We look forward to serving you!brbrThere will be a $25 per person (12 yrs and older) resort fee that will be charged at the time of arrival.

Wrap-Around Deck, Bay Views, Private Pool & Hot Tub - OFFICIAL RESORT LISTING

Captiva, Florida, United States

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$732.19

Hakuna Matata – Worry-Free Island Living on North CaptivabrbrEscape to Hakuna Matata, a bright, beautiful 3-bedroom, 2-bath home located on the car-free paradise of North Captiva Island — just a short ferry ride from Florida’s Southwest coast. Perfect for families, groups, and couples, our home is designed for pure relaxation.brbrEnjoy a spacious open floor plan with marble floors, a granite kitchen and minibar, and cozy spaces both indoors and out. The Owner’s Suite features luxury linens, a plush king sized mattress, a walk-in shower and a private deck. The second bedroom offers another king sized bed and a peaceful outdoor sitting area. Our third bedroom features a queen sized bed and a triple bunk, perfect for families or a third couple. These two bedrooms share the second bathroom, also with a walk-in shower.brbrFully stocked for your stay, the kitchen includes stainless steel appliances, a Keurig and coffee maker, blender, Insta-pot, and reverse osmosis drinking water. Share meals around the large indoor table or on the scenic screened porch overlooking nature.brbrCool off in the private pool, or gather in the shaded entertainment area with a brand-new pool table, ping pong, TV, grill, outdoor shower, and games.brbrTwo golf carts are included for exploring the island, enjoy the 350-acre preserve(walking or biking only), stunning beaches, and breathtaking sunsets. Plus, you’ll have access to the exclusive Island Club with pools, a poolside bar, kayak and bike rentals, and more.brbrNorth Captiva offers world-class shelling, fishing, stargazing, and unforgettable wildlife encounters — dolphins, manatees, tortoises, and nesting sea turtles.brbrYour stay includes personalized concierge service, easy ferry transportation tips, and optional grocery delivery right to the island.brbrAt Hakuna Matata, you’ll discover a place where stress disappears and memories are made. We can’t wait to welcome you!

Luxury island home with a private pool, game area, golf carts, club access.

Captiva, Florida, United States

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Bath

Sleeps

$675.85

Nama-Stay is located on a barrier island in southwest Florida. In fact, the only way to get to the island by boat or private plane. This is THE spot for a relaxing beach vacation. Enjoy your own private pool along with all the amenities that are offered by the island's private club. The house also comes with two golf carts so you can easily explore all the island has to offer. This house is a 30 second golf cart ride to the Island Club and a 1 minute golf cart ride to beach access!

Newly Remodeled 4 Bedroom House w Private Pool

Captiva, Florida, United States

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Bath

Sleeps

$623.97

Do you like your dessert first Do you like the sweet taste of paradise Then our “Cupcake” is for you! This delightfully sweet 3 bedroom, 2 ½ bath private home at 11461 Dickey Lane is situated on the quiet side of Captiva Village and close to everything. The Village is known for its restaurants, shops and easy beachy atmosphere. Our “Cupcake” is an easy walk down Laika Lane to the beautiful white sand beach and a half block walk to the bay.brbrYou will enjoy the many delightful colors of “Cupcake”. Swim in your own large heated and caged pool or enjoy the relaxation of the hot tub. You can read a book on the large back deck overlooking the pool area or have breakfast watching the world go by on the front deck. brbrInside “Cupcake” the cathedraled ceiling family room has comfortable furniture with a large screen TV, DVD Player, Wi-Fi and a Sonos speaker system. The house was professionally designed and completely updated in 2012 and lovingly maintained. The 3 bedrooms, painted in fun and whimsical colors, are spacious and each includes a flat screen TV. Bedroom 1 has a King bed, bedroom 2 has two twin beds (which can be converted to a King on request) and, located on the opposite side of the house, the private master suite has a new King bed and private en-suite. These bedrooms will have you sweetly dreaming of the memories you’ve made today and the memories you’ll make tomorrow. Check out the yummy and colorful countertops in each bathroom and the kitchen. You’ll smile every time you see them!brbrSpeaking of the large airy kitchen, it is fully equipped and has a breakfast bar area and a separate dine in area. The full-size washer and dryer are near the Kitchen. A gas BBQ grill is waiting for your use in the fully screened lanai.brbrAs in a real cupcake, it’s not all about the icing, the cake underneath the icing is also enjoyable. Our “Cupcake” is no exception. There is ample parking. The fully screened ground floor pool area is a great gathering space for conversation, playing cards, games or enjoying your favorite beverage as you watch the swimmers in the pool. And you will appreciate the large covered area for fun and games in case of inclement weather or to escape the Florida sun for an afternoon nap! With this “Cupcake” you can enjoy the whole thing….with no calories!brbrOnce you arrive at “Cupcake” park your car and leave it until it is time to go back to reality. Remember, “Cupcake” is a short walk to the beach and the bay. Walk to famous Andy Rosse Lane with its restaurants and shops. “Cupcake” includes a selection of beach toys, coolers, chairs, beach umbrellas and beach towels. A beach cart is provided to make the short trek to the beach very easy. Also, you can rent bicycles, surfboards and other fun beach toys at Yolo. How about renting a boat for the day at Jensen’s Marina Cruise to North Captiva Island for lunch and dolphin and manatee watching. Keep in mind that it is only a short walk to everything that the Village offers.brbrSome visitors like to see the sun rise on the bay side…..we prefer to watch the sun set on the beach. Take a cooler, set up the beach chairs and take a lot of beautiful pictures as the sun sets over the gulf off the island of Captiva. Then pack up and take a stroll to the Mucky Duck, the Bubble Room or other delicious restaurants nearby, many of which have outdoor dining and live music.brbrIn the morning you might like to take a short walk to Starbucks for your favorite coffee. Enjoy it there, or on the sunny front deck of “Cupcake”.brbrThere is much to discover on Captiva Island. We wish you sweet dreams and mouth-watering memories as you experience the Village of Captiva and our fun and relaxing cottage called “Cupcake”. It would be a pleasure to have you as our guest!br

It's A Colorful Cupcake World On Captiva Island

Captiva, Florida, United States

Bed

2

Bath

6

Sleeps

$955.44

Welcome to Mint Julep, a beachfront island retreat on the quiet, unspoiled shores of North Captiva Island. This spacious and well-appointed home offers direct private beach access and sweeping Gulf views, making it an ideal escape for families and groups seeking a relaxed and memorable island vacation.brbrProfessionally hosted as an Admiral Home by The Island Club, Mint Julep combines comfort, convenience, and true island living in one of Florida’s most peaceful destinations. Wake to the sound of waves, enjoy easy beach access throughout the day, and unwind each evening watching the sun set over the Gulf.brbrTHE SPACEbrbr4 Bedrooms | Multiple Bathrooms | Sleeps up to 10brbrPRIMARY BEDROOM SUITE #1brbrKing-size bed with pillows and linens providedbrbrPrivate en-suite bathroombrbrQuiet beachfront settingbrbrPRIMARY BEDROOM SUITE #2brbrKing-size bed with pillows and linens providedbrbrPrivate en-suite bathroombrbrComfortable and private retreatbrbrQUEEN BEDROOMbrbrQueen-size bed with pillows and linens providedbrbrConvenient access to a full bathroombrbrBUNK ROOMbrbrTwo sets of bunk bedsbrbrIdeal for children or additional guestsbrbrLIVING AND GATHERING AREASbrbrOpen-concept living room with comfortable seatingbrbrFlat-screen TV and Bluetooth speakersbrbrKITCHEN AND DININGbrbrFully equipped kitchen with gas stovebrbrEverything needed for preparing family mealsbrbrOUTDOOR LIVINGbrbrExpansive covered beachfront porch with seatingbrbrGas grill for outdoor diningbrbrTwo outdoor showers for rinsing off after the beachbrbrDirect private beach access just steps from the homebrbrIf you have questions about the layout, beach access, or planning your stay, please contact us. Our team is happy to help.brbrPROPERTY ACCESSbrbrGuests enjoy full private access to the entire home, including all interior living spaces, covered porches, grill, outdoor showers, and direct private beach access.brbrOne golf cart is included with your stay for island transportation.brA second golf cart is available to rent for $50 per day and must be arranged in advance.brbrGuests also enjoy full access to Island Club amenities, including:brbrTwo poolsbrbrHot tubbrbrArcade roombrbrLuxury bathrooms and showers at the poolbrbrHalf-court outdoor basketballbrbrKayaksbrbrStand-up paddleboardsbrbrFat tire beach bikesbrbrBeach chairs and beach umbrellasbrbrINTERACTION WITH GUESTSbrbrWe respect guest privacy while remaining readily available whenever assistance is needed.brbrAs an Admiral Home, your stay includes full support from The Island Club team. Our on-island staff can assist with ferry coordination, luggage assistance, grocery delivery, golf cart arrangements, and personalized recommendations.brbrNEIGHBORHOOD OVERVIEWbrbrMint Julep is located on North Captiva Island, a secluded, car-free barrier island known for pristine beaches, abundant wildlife, and relaxed Old Florida charm.brbrGuests enjoy shelling, fishing, bird watching, and exploring nearby wildlife preserves in a peaceful island environment where nature takes center stage.brbrGETTING AROUND / TRANSITbrbrIsland Access: North Captiva is only accessible by boat or small private plane. No cars are allowed. Parking at the mainland Welcome Center is $10 per day.brbrGolf carts are the primary mode of transportation on the island. One golf cart is included with this home, with an optional second cart available for $50 per day.brbrThe nearest commercial airports are Fort Myers (RSW) and Punta Gorda (PGD). Guests should plan ahead for groceries and essentials, as on-island shopping options are limited.brbrIMPORTANT NOTES AND HOUSE RULESbrbrLuggage Assistance Included (Admiral Home):brAs an Admiral Home guest, luggage assistance is included with your stay. An Island Club team member will load your luggage onto the ferry and deliver it directly to the home upon your arrival. A team member will also be waiting at the ferry dock to assist and ensure a smooth arrival experience.brbrGolf Cart Damage Deposit:brA $2,000 pre-authorization damage deposit hold will be charged to your card on file three days before check-in and released within one week after checkout, pending golf cart inspection.brbrPet Policy:brbrDogs up to 60 lbs are welcomebrbrAdditional cleaning fee and pet deposit applybrbrPets are not permitted on furniture or bedsbrbrAdditional Notes:brbrPack n play and high chair providedbrbrPlease stock up on groceries and essentials before arrival or arrange deliverybrbrHouse Rules:brbrNo smoking inside the homebrbrNo parties or events allowedbrbrQuiet hours are from 10:00 PM to 8:00 AMbrbrCheck-in at 4:00 PM and check-out at 10:00 AMbrbrGuests must follow all local laws and guidelines designed to protect North Captiva Island’s wildlife and natural environment

4BR Beachfront North Captiva Home with Golf Cart

Captiva, Florida, United States

Bed

Bath

Sleeps

$764.9

Dreaming of a sprawling, stunning Captiva Island home that’s just steps away from the beach Longing for a private poolside oasis under swaying palm trees Welcome to the Palm & Shell, a stunning vacation home that offers the best of both beachside and poolside luxury. brbrWe believe every day on Captiva is something to celebrate and we've furnished the Palm & Shell with that philosophy in mind. Our huge chef’s kitchen and dining area are appointed with every convenience for dining in, carrying out and everything in between. Our spacious and comfortable living room offers plenty of gathering space and family-friendly amenities, including a smart TV, DVD collection, high-speed Wifi, large reading library and card and board games. brbrThe soaring, screened atrium, lanai and pool bar will surely be a favorite gathering spot for relaxing, grilling, and chilling. Enjoy our large, heated pool and hot tub, day and night. brbrOur private beach path is just steps from Captiva’s famed South Seas beach. We provide beach chairs, umbrellas, a beach cart, beach toys and everything else you’ll need. All you have to worry about is enjoying yourself! brbrThe Palm & Shell has 5 luxurious bedrooms and sleeps up to 12. And while the home doesn't include resort amenity access, you won't want to leave except to enjoy some of the many nearby restaurants, shops and island attractions. You can even rent a golf cart to get around quickly and easily. brCome make magical Captiva memories at the Palm & Shell. We look forward to welcoming you soon!brbr** What better way to explore with our 4 seater golf carts There are 2 golf carts for rent to accomodate a big group! Inquire with Dream Vacations to add to your stay**brbrWhile you won't have resort amenity access, you won't need it as our home has everything you'll need and there are several restaurants just outside the gates of the resort for you to enjoy. brbrImportant Note: The elevators are currently functional; however, as they are mechanical items, we cannot guarantee they will remain operational during your stay. Please note that refunds will not be issued in the event of elevator malfunctions.brbrImportant Note:brPlease be aware that, as of now, there are no ongoing repairs or construction within South Seas Resort. However, should any construction occur during your stay, kindly note that we do not issue refunds for disruptions caused by repairs or maintenance that are beyond our control.brbr**Shared tennis court is still under maintenance due to the hurricane. As an alternative, you may use the beach villas tennis court.**brbrFollow us on Instagram @THEPALMANDSHELL

The Palm & Shell Captiva Island Luxury Vacation Rental Home

Captiva, Florida, United States

Bed

Bath

Sleeps

$1223.88

This five-bedroom channel-front estate home is the perfect place for a memorable friends and family vacation. This stunning pool home is located on the Roosevelt Channel. Watch dolphins, manatees, and sea birds from one of the many decks. A short stroll across the street to the left to Blind Pass/Turner Beach, where you can view world-renowned sunsets! * This property does not have deeded beach access.brbrThis estate home has everything you need for an amazing vacation. Walk into the large living room with an open ceiling to the 2nd level. The huge dining room features updated furnishings and seating for 10. The large kitchen has plenty of cabinet space, large countertops, and updated appliances.brbrLounge in one of the two expansive living rooms with views over the tropical grounds and Roosevelt channel. The second living room has a new 85-inch flat screen television with surround sound, a large sectional sofa, and a pool table. It also opens to views of the channel and lanai. There are also two King bedrooms on this floor. Both have flat-screen televisions and private full bathrooms. The 2nd floor features another king bedroom with a private bathroom and views of the channel. Two more bedrooms complete the 2nd floor. The first bedroom has a king bed and a day bed, the second bedroom has a queen bed. Both bedrooms have flat-screen televisions and share a full bathroom with an updated shower.brbrThere are multiple decks to view the water, watch the wildlife, or just relax. br*Smart televisions with streaming services only*br The lower level features a large heated pool, hot tub, seating area, grill, kayaks, one paddleboard, and two life jackets. There is also a pack and play and a high chair. Everything you need to make lasting memories! brbr*The dock cannot accommodate a boat but is great for fishing*brbrKingfisher Vacations will only book reservations up to 51 weeks in advance.brAll our properties have contact-free check-in; no need to stop at the office (or a stop light, none of those here)!

Five bedroom Channel Front Estate home on Captiva! Perfect for Family & Friends

Captiva, Florida, United States

Bed

Bath

Sleeps

$547.26

4 bedrooms each with its own bath; arcade games, pool table, and ping pong. Sleeps 10brYou’ll lavish in the breeze of the ocean from this 4-bedroom home’s rooftop captain deck after beach walks, swimming in the private pool, dipping in the hot tub or gazing at the stars.brbrEveryone will find their own way to relax, whether by the pool, playing on one of the 3 arcade games, challenging someone with a game of pool or ping pong, or by resting on one of the many indoor or outdoor living spaces.brbrTop to bottom -- this beautiful home has been completely redecorated and upgraded with designer touches. It comfortably sleeps 10! Elevator service from the ground level up to the top.brbrAn exquisite, luxury home awaits you on private Wightman Lane. Just steps from the serenity of the ocean or the convenience of the Village, Captiva Breeze is a 4 bedroom, 4 bath luxury vacation oasis with spacious indoor and outdoor living areas, a private heated pool and spa tub with waterfall and porches galore, including a rooftop captain’s walk with partial views of the bay and Gulf of Mexico.brbrOn the main living level, you will find a living room with cathedral ceilings; incredible gourmet kitchen with granite countertops, a wine chiller and bar area; the master bedroom king suite; a guest suite with twin beds; full bathroom with access from the living area or bedroom; and full-sized washer and dryer. Kitchen and dining areas, and the master suite all open up to the screen-enclosed lanai overlooking the pool.brbrThe king master suite includes an en-suite bathroom with a jet tub large enough for two, a glass-and-tile oversized shower, dual-sink vanity, a walk-in closet, and a separate toilet chamber. Private stairs lead you from the master suite to the pool!brbrThe upper level of the home includes two more beautiful and comfortable bedrooms, each with its own private en-suite bathroom. One room includes a King-sized bed. The other oversized room includes a King bed and Twin bunk beds with safety stairs, comfortably sleeping up to 4 in one room. Both rooms have private access to the rooftop sundeck. The modern floor plan, multiple living areas, and elevator make this a fabulous vacation home for any family!brbrOutside this luxurious home is an oversized and heated pool with spa tub and waterfall, four authentic 'Free Play' arcade games, an outdoor pool table, a ping-pong table, a gas grill, and lush landscaping for your private tropical oasis!brbrCaptiva Breeze has been upgraded with a state of the art whole house air purification system for your safety and comfort. Features of this system include:brbr* Dual ionizers to reduce airborne particulates (dust, dander, pollen, mold spores)br* Kills up to 99% of bacteria, mold, and virusesbr* Reduces sneeze germs by 99% in the time a sneeze can reach three feet.br* New zinc ions kill 99% of viruses on the surfacebr* Allows customization of the advanced oxidation plasma output.brbr*Important Note: This rental does not include beach chairs or umbrellas. Instead, we’ve partnered with VayKLife to provide you with a credit toward beach essentials like chairs, umbrellas, coolers, wagons, and more—so you can pack light and still enjoy everything you need for a perfect day at the beach. While some of our homes may have beach gear on-site, availability varies, and we cannot guarantee specific items will be provided. With VayKLife, you get to choose exactly what you need, and they’ll deliver it right to your door for added convenience. Your booking confirmation includes a link to VayKLife’s site, where you can browse their full selection and easily redeem your credit. It’s just one of the ways we help make your stay as seamless and enjoyable as possible.brbr***Due to the aftermath of the storms Helene and Milton, the island is currently in a restoration phase. Please be aware that many amenities may not be open or readily accessible during your visit, including limited restaurant options and activities. Additionally, nearby ongoing construction may create noise and other disturbances that we have no control over.***

Captiva Breeze Pool Home near beach

Captiva, Florida, United States

4

Bed

4

Bath

10

Sleeps

$621.64

This 3BR, 3BA island retreat sleeps 8 and is less than a one-minute walk to the beach (we timed it—with flip-flops). While some photos don’t yet show it, we’re in the process of refreshing every room with bright paint, a whitewashed plank ceiling in the great room, new furniture, and playful coastal decor—including cheeky touches like alligator wallpaper and bold Southern charm.brbrIt’s casual comfort meets curated beach vibes—with plenty of space for families, including baby gates, high chairs, and other thoughtful amenities for traveling with little ones. Outside, you’ll find a private, heated saltwater pool (heating available for $35/day in cooler months.) brbrA 4-seater golf cart is included with your stay for exploring the island at your own pace. Need more room Additional carts can be rented from Boats and Fun or the Island Club.brbr2025 rates are lower while we put the finishing touches on the space—so if you’re cool booking on a little faith, you’ll score a sunny deal. No painting or decor work will ever be done during guest stays; all updates happen between bookings.brbrAfter you book, you’ll receive an extensive digital guest guide to help you plan everything from groceries to ferry logistics. We also have a wonderful property manager who lives right on the island—she’ll meet you at the ferry, help get you to the house, show you around, and is available throughout your stay for any questions or local tips.brbrPlease note: Check-out is at 9:00 AM (VRBO doesn’t allow us to list that time accurately). The hot tub is no longer on the property, though it may appear in a few older photos.

Private Saltwater Pool + Steps to Beach

Captiva, Florida, United States

Bed

Bath

Sleeps

$647.52

Beach House 15 is located within the gates of the Island Resort. Our four-bedroom/three-bathroom home features over 2000 sq ft of living space, perfect for up to 10 guests. The spacious living room has comfortable seating, including a queen-sized sleeper sofa, flat panel TV, and leads directly out to the screened lanai, perfect for a morning cup of coffee while watching the gentle waves break against the sand. While Captiva Island has several wonderful restaurants, the home has a full kitchen and dining area to prepare meals for your family and friends during the week. In terms of bedding, the home has a spacious primary bedroom suite with a king-sized bed and an en-suite bathroom. The second bedroom has two queen-sized beds with an en-suite bathroom. There are two additional bedrooms, one with a queen bed and the other a bit smaller and has a full bed with a full bathroom in between. Our association features two heated pools, a tennis court, and BBQ grills. The home has high-speed wireless internet and smart TVs. While our home is not affiliated with the Resort, and resort amenities are not included, you will still have access to everything outside of the resort and never have to pay a daily resort fee. Save up to 50% compared to resort rates and book direct. Weekly minimum stays are required, and no pets, unfortunately. brbrImportant NotesbrbrPrivate ManagementbrThis condo is privately managed and not affiliated with the resort. Guests do not have access to resort amenities.brBeach GearbrBeach chairs and umbrellas are not included. Instead, your stay includes a VayKLife credit for beach essentials such as chairs, umbrellas, coolers, wagons, and more. Delivery is included. On-site availability cannot be guaranteed. Your booking confirmation includes a link to redeem your credit.brConstruction & MaintenancebrCurrently, there are no ongoing repairs or construction within the Resort. Should any occur during your stay, refunds will not be issued for disruptions caused by maintenance or repairs beyond our control.brStorm ImpactsbrDue to Hurricanes Helene and Milton, access to some amenities may be limited during your stay.br

Beach House 15 - Direct gulf front home with pool and tennis

Captiva, Florida, United States

Bed

Bath

Sleeps

$998.72