Vacation Home Rentals By Owner In Captiva, FL

Anchored Here – One House from the Beach with Gulf Views and Private PoolbrbrJust 30 seconds from the sugar-soft sands of Captiva Beach, Anchored Here is the ultimate family beach retreat—offering luxury, space, and location all in one. This three-story tropical getaway sits just one house from the Gulf and features side water views from two expansive balconies. With a private pool and spa, multiple living areas, and flexible check-in dates, this is a perfect choice for your next island escape.brbrRelaxed Luxury with a ViewbrThis thoughtfully designed home welcomes you with a light-filled entry and access to the oversized three-car garage. The ground-level indoor/outdoor entertainment space features a stylish bar area with 8-foot sliding glass doors opening to a private stone patio, complete with a lush tropical pool, hot tub, outdoor shower, gas grill, and waterfall feature—your own personal oasis.brbrThe second level is dedicated to comfort and rest. A cozy living room with a sectional sleeper sofa and flat-screen TV provides a quiet space to unwind. The master suite features a king bed, a sitting area, a private balcony, dual walk-in closets, and a spa-inspired en-suite bath with a soaking tub and separate tiled shower. Two additional guest suites each include private bathrooms—one with a queen bed and the other with two twin beds, perfect for families or friends traveling together. A full laundry room with a large-capacity washer and dryer is also on this level. Upstairs, the third floor offers stunning partial Gulf views from two oversized balconies. An open-concept layout includes another plush living room, a dining table for eight, a four-person game table, and a fully equipped gourmet kitchen with custom cabinetry, granite countertops, high-end stainless appliances, and a breakfast bar. A full bathroom with a shower/tub combo is also on this level, making this space perfect for entertaining or simply soaking in the views.brbrAmenities & Important NotesbrPrivate heated pool and spa with waterfallbrThree bedrooms, a sleeper sofa, and four full bathroomsbrTwo spacious living areasbrMultiple balconies with partial Gulf viewsbrGourmet kitchen with premium appliancesbrWasher and dryerbrLarge indoor/outdoor entertaining space with wet bar and grillbr30-second walk to Captiva BeachbrFlexible check-in datesbrbrbrPlan Your Island Escape - Whether you're catching the sunset from your Gulf-view balcony, enjoying a poolside cocktail beneath the palms, or walking barefoot to the beach, Anchored Here invites you to experience the magic of Captiva in comfort and style. With flexible dates, generous space, and an unbeatable location, your perfect beach vacation starts here.brbrKingfisher Vacation Rentals will only book reservations up to 51 weeks in advance.brAll of our properties have contact-free check-ins.

Ready for Rentals- All New Kitchen- Stunning Interior

Captiva, Florida, United States

Bed

4

Bath

10

Sleeps

$805.01

Twin Dolphins : Canal Front : Private Pool • Crow’s Nest ViewsbrbrWelcome to Twin Dolphins, your private island escape on North Captiva. Located at 621 Rum Road, this beautiful canal-front home offers the perfect mix of relaxation, comfort, and unforgettable views.brbrSleeping up to 8 guests, Twin Dolphins is ideal for families or groups looking to enjoy laid-back island living with all the conveniences of home.brbrThe home also features an elevator, making it easy to move between levels and enjoy a more comfortable stay.brbrThe SpacebrbrPrimary Suite: King bed with private ensuite bathroombrGuest Bedrooms: Two queen bedroomsbrBunk Room: Perfect for kids or additional guestsbrBathrooms: 2.5 bathrooms + outdoor showerbrSleeps: 8 guestsbrbr Kitchen & LivingbrbrFully stocked kitchen with cookware, dishes, and everything you need to prepare meals at homebrOpen-concept living and dining areas designed for gathering and relaxingbrComfortable seating and plenty of space for your group to unwind after a day in the sunbrIdeal for family dinners, game nights, or relaxed island eveningsbrbrOutdoor Living & AmenitiesbrbrPrivate screened-in heated poolbrLocated on a canal with dockage for two boatsbrCrow’s nest lookout with stunning 360-degree island viewsbrIndoor seating in the crow’s nest facing east—perfect for peaceful sunrise mornings with coffeebrOutdoor shower for easy rinse-off after the beachbr4-seater golf cart included with your staybrbrThe ExperiencebrSpend your days boating right from your backyard, cruising the island by golf cart, relaxing poolside, or heading to the beach. Start your mornings in the crow’s nest watching the sunrise, and end your evenings enjoying everything that makes North Captiva so special.brbrConcierge ServicesbrTo make your stay seamless, Shally’s Seashells Property Management offers concierge-style guest services so you can start relaxing the moment you arrive.brbrWe can assist with:brbrDockside meet-and-greet with luggage assistancebrGolf cart transportation to the home upon arrivalbrPre-arrival grocery, liquor, and seafood stocking servicesbrLocal recommendations and personalized assistance throughout your staybrbrWhether you’d like the kitchen stocked before you arrive or help getting settled in, our team is here to make your North Captiva vacation effortless and enjoyable.

TWIN DOLPHINS: Screened in Pool, Two Docks, Elevator, Golf Cart, Sleeps 8

Captiva, Florida, United States

4

Bed

Bath

8

Sleeps

$1130.99

Slip into island time the moment you arrive at Poppy’s Paradise, a beautifully updated four-bedroom, four-bath vacation home tucked away on quiet Chapin Lane in the Village of Captiva Island. Just 400 feet from the sugar-white sands of the Gulf, this elevated coastal retreat offers private beach access and the rare luxury of being able to stroll to the island’s charming shops and restaurants whenever the mood strikes.brbrStep inside and feel the relaxed rhythm of island living. The main level opens into a bright, welcoming living space designed for gathering after long beach days. The fully equipped kitchen features granite countertops, stainless steel appliances, and everything you need to prepare anything from a quick breakfast before the beach to a leisurely family dinner. Just beyond, the newly upgraded screened porch creates the perfect setting for morning coffee, sunset cocktails, or an evening meal in the warm tropical air.brbrWith space for up to ten guests, the home offers comfort and privacy for everyone. Two spacious primary suites provide peaceful retreats, including one privately situated on the upper level with its own ensuite bath featuring a jetted tub and walk-in shower. The second primary suite is located on the main level with its own bath and generous storage space. A third bedroom with two full beds is paired with a nearby full bath, making it ideal for families or friends traveling together.brbrDownstairs, a separate entertainment level adds another layer of fun to your stay. Accessible via the back stairway, this private space features a game room with a ping pong table, pool table, seating area, flat-screen TV, refrigerator, and bar area for casual gatherings. A fourth bedroom with two twin beds and a private bathroom with walk-in shower is also located on this level, creating a great hideaway for teens or guests who appreciate extra privacy.brbrOutside, your own tropical oasis awaits. The spacious patio and pool area are designed for relaxation, surrounded by lush greenery that provides a sense of seclusion. Lounge chairs invite you to soak up the Florida sunshine, while the heated private pool and connected hot tub offer the perfect way to unwind after a day at the beach. A stainless steel gas grill nearby makes outdoor dining easy, whether you are preparing fresh seafood or a simple island barbecue. For families traveling with young children, a portable child safety fence is available and can be placed around the pool area for added peace of mind.brbrInside the home you will find thoughtful amenities throughout, including five flat-screen TVs, four DVD players, a CD player, beach towels, washer and dryer, garage parking, and complimentary Wi-Fi.brbrOne of the most beloved features of Poppy’s Paradise is its location. From here you can easily walk to the beach for sunrise shelling, wander into the village for dinner, or explore the laid-back charm that makes Captiva Island such a special destination.brbrThis home sleeps up to 10 guests and offers approximately 2,300 square feet of living space.

Slip into island time the moment you arrive at Poppy’s Paradise

Captiva, Florida, United States

Bed

Bath

Sleeps

$710.26

Welcome to The Compass Rose:brbr Discover North Captiva Island: A hidden gem off Florida’s Gulf Coast, North Captiva is a car-free, boat-access-only paradise just 20 minutes by water taxi. The island offers Caribbean-style seclusion with modern comforts. Explore trails, wildlife-rich preserves, and enjoy local dining at Mainstay’s, Mango’s Island Grill, and Over the Waterfront.brbr The Home: Spacious. Elegant. Fun.brbrWith over 4,000 sq ft (2,500 sq ft climate-controlled), The Compass Rose sleeps up to 10 guests (8 adults max) across 4 king bedrooms.brbr✔️ Private Heated Poolbr✔️ 2 Golf Cartsbr✔️ 4 Kayaks + Beach Gear (towels, chairs, umbrellas)br✔️ Games Galore – Foosball, ping pong, cornhole, board games and a ⛳Golden Tee arcade gamebr✔️ Fully Stocked Kitchen – Double oven, cooktop, Keurig + drip coffee, countertop ice maker, Instant Pot, propane grillbr✔️ Multiple Fridges – 2 full-size + 4 mini-fridgesbr✔️ High Speed Wi-Fi + Smart TVs + YouTube TVbrbrPerks & Amenities:brbr Private heated pool for refreshing dips.br Entertainment includes ping pong, foosball, and cornhole.br ‍♂️ Explore with 20 miles of bike paths on the island.br Water activities include 4 complimentary kayaks.br Two golf carts provided for convenient island exploration. All golf cart drivers must sign a golf cart rental agreement.brbrOutdoor Living:brbr Enjoy the rooftop deck, 40 ft above ground, for panoramic views of the Gulf and beyond.br Cook on an outdoor propane grill situated conveniently off the gourmet kitchen deck, facilitating amazing alfresco dining.br For more outdoor adventures or rentals such as bikes, paddleboards, boats, and more, visit Boats and Fun located on the island.brbrThings to Note:brbr Not Included:brbr• Food, beveragesbr• Shampoo & shower gelbr• Airport or boat transportationbrbr Rental Terms & Policies:br• Maximum: 10 guests (8 adults max)br• Must be 25+ years old to drive cart, must provide driver's license to drive cartbr• All Golf Cart drivers must sign a Golf Cart Agreementbr• No parties or unregistered guestsbr• Primary renter 25+ years old pleasebr• Pets considered with prior approvalbr• $500 security deposit requiredbr• $300 cancellation fee applies to all cancellationsbr• Signed rental agreement + valid government ID requiredbr• Credit card payments must match booking guest’s name & IDbrbrEmbrace the secrets of North Captiva at The Compass Rose, where unrushed island charm meets unparalleled beach living. Perfect for families and friends looking for a unique getaway.

Panoramic Ocean Views, Sleeps 10, Heated Pool

Captiva, Florida, United States

Bed

Bath

Sleeps

$414.28

Second Star is a peaceful place with a state-of-the-art interior, a unique 3 bedroom, 2 bath, 1450 sf home, nestled in palm trees overlooking Safety Harbor Lake. Watch the wildlife from the balcony daily! Let Second Star guide you to a special island vacation.brbrOur home features an open floor plan that allows air and light to flow. It has a reverse floor plan, all bedrooms are on the first level. A small spiral stair leads too the living/kitchen area with a deck off the living area overlooking Safety Harbor Lake where wildlife abounds. brbrThe interior follows a modern, yet warm pattern. Every detail has been paid attention to. The master bedroom has a king bed, the second bedroom a king bed and the third bedroom has 2 twin beds. Plenty of comfortable space for 6 guests. 4 adults maximum.brbrThe outdoor area features an open space , where palm trees provide shade on a hot day. An outdoor shower awaits our guests for an immediate cool down. Lounge area downstairs includes a private hot tub and comfortable seating along with overhead fans.br brOne door away, our guests can dive into a beautiful newly updated (heated) pool that is exclusively for guests of the Safety Harbor Community. Right next to the pool, our guests find a tennis court and a pickle ball court (rackets and balls in Second Star for guests to use) The courts are surrounded by tropical vegetation. SHC private beach access to a secluded beach is just around the corner. Second Star offers its own book library for our guests as well as a state of the art entertainment system with 4 smart TV's. Additional items such as board games, and books are in Second Star as well as in SHC clubhouse for guests to borrow:)brbrWe recommend guests bring their own Amazon Stick or Apple TV to insert into our Smart TV's for fast streaming with our NEW STARLINK Hi Speed internet service :)brbrWe love to cook and like to pass this passion on to our guests. Our home is equipped with all you need to prepare delicious meals (including a Weber grill, food processors and many spices), a counter top nugget ice maker and new appliances, the stove has options for convection bake and broil as well as air fry option.brbrAll linens are provided, there are a surplus of beach towels for our guests to use. Each bathroom has a hairdryer as well. Dishwasher soap, Dish soap, Laundry soap, Hand soap are all provided! There is shampoo and conditioner available not brand specific. If you prefer certain brand toiletries please bring your own. Beach chairs and umbrella's are available for use. Do not overpack! You will find North Captiva very casual and you have a washer and dryer for your use:)brbrOur guests will have access to a newly updated heated pool, tennis court, pickle ball court and private beach access & boat dock. brbrIf you plan to arrive on your private boat and you would like to reserve a boat dock at SHC wharf there is an additional fee which will be added to the rates quoted here. Safety Harbor Club requires all guests requesting to reserve a boat slip within SHC provide boat registration and boat insurance information at time of booking. We will provide that information to SHC office. Once approved by SHC the office provide guests with a boat guest pass which must be displayed on the boat during your stay. If not approved we will let you know immediately.brbrIf you plan to arrive via private airplane, we are members of Salty Approach Airstrip; therefore, a guest pass for Salty Approach Airstrip can also be arranged for an additional fee.All registration and insurance information for an airplane must be provided at time of request. We will forward all information to Salty Approach, LLC for an approval. Once approved we will provide guest with all information regarding landing and tie down on Salty Approach with a guest pass. Again, if not approved we will let you know immediately. brbrNorth Captiva Island is the perfect place to kayak, boat, relax, fish, shell, walk, bike, meditate and spend time on endless beautiful beaches! The south end of the island is beautiful state protected preservation land, accessible by foot, home to turtles and birds. You can watch dolphins, manatee and even otters on the bay side of the island often!brbrWe fell in love with North Captiva Island on our first visit and are thrilled to be able to share Second Star with our guests. It is a very special place for us where we watch the sun set over palm trees from our balcony, listen to the soft waves on endless miles of beaches, feel the sand between our toes and smell salt water and exotic flowers year round while sitting and watching the wildlife. Please be sure to help preserve the beauty of this enchanted tropical hideaway by only observing its treasures. brbrWe are happy to answer your questions and help you to make travel arrangements to and from the island.

Escape to private lakefront home, steps to gulf, with STARLINK HiSpeed Internet

Captiva, Florida, United States

Bed

2

Bath

6

Sleeps

$3998.07

Indiana Jones Adventure Meets Luxury Island Living | Rare Fly-In / Boat-In Captiva EstatebrSet along the waters of Pine Island Sound with views stretching toward the Gulf of Mexico, this extraordinary Upper Captiva property offers one of the most unique lifestyles in Southwest Florida. Situated on approximately 1.16 acres, this private island retreat is accessible by boat or private aircraft via Salty Approach Airstrip (FL90), Upper Captiva’s private 1,800-foot grass runway. The property also includes a hangar below the home, making it ideal for aviation enthusiasts.brbrDesigned for those who crave privacy, adventure, and a true sense of escape, the residence features 5 bedrooms, 5 bathrooms, and more than 3,900 square feet crafted to capture panoramic water views and unforgettable sunsets. A private elevator services all four levels. Inside, the home offers spacious living and entertaining areas with marble, tile, and wood flooring throughout. The chef’s kitchen is appointed with premium appliances, wine and beverage refrigeration, an ice maker, and an open layout ideal for hosting.brbrOutdoor living is exceptional, with expansive terraces and gathering spaces overlooking the water. A new Trex waterfront deck leads to a private composite dock with boat lift, ideal for a 40-foot Viking for serious fishing adventures, plus a fast boat such as a Nor-Tech or Midnight Express for island-hopping and cruising. The dock may also accommodate a seaplane. Additional features include a whole-house generator, hurricane impact windows and doors with shutters, outdoor kitchen, poolside cabana, exercise room, multiple entertaining spaces, well water, septic, propane gas service, a private sauna, and every luxury appointment in place. The 29'5 x 36'7 hangar-style garage offers substantial space for aircraft.brbrThis is more than a residence. It is a gateway to one of the most extraordinary waterfront experiences in Southwest Florida. Spend your mornings heading out by Viking for world-class fishing, your afternoons cruising to nearby islands, and your evenings soaking in panoramic sunsets over Pine Island Sound. With exceptional access to Boca Grande’s renowned deep-water fishing right from your back door, this estate is designed for the buyer who expects the extraordinary.brbrAnd the island lifestyle extends beyond the dock and runway. Upper Captiva offers beloved gathering spots where owners and guests can unwind and enjoy the social side of island living, including Mango’s, Mainstay North Captiva, formerly Barnacles, Over the Waterfront at Safety Harbor Club, and The Boathouse. It is the kind of place where a day of fishing or island hopping flows naturally into sunset cocktails, waterfront dining, and relaxed evenings in one of Southwest Florida’s most exclusive and unforgettable communities.

Private Beachfront Oasis and Pool on Upper Captiva accessible by boat or plane

Captiva, Florida, United States

Bed

Bath

Sleeps

$685.73

Sea Star is a exquisite new vacation beach home fully equipped and built to a high standard. The home is a spacious one story 1600 square foot open floor plan with raised ceilings for an extra spacious feel. This new home is tastefully furnished and setup with 4 TVs. The kitchen is a lovely well-appointed designer kitchen open to the living and dining areas - just perfect for entertaining. Each bedroom is spacious with luxuriously comfortable beds. The open deck looks down at the spacious pool surrounded by a smooth, cool paver pool deck. There are charcoal and gas grills for your convenience. North Captiva Island is accessible only by boat, and is golf cart, bicycle, and pedestrian traffic only. A new four-seater cart comes with your rental for licensed drivers only. Make Sea Star part of your next dream vacation!

SeaStar North Captiva, Private Pool, Near Beach

Captiva, Florida, United States

Bed

Bath

Sleeps

$599.87

brbrPLEASE CONTACT US ABOUT DISCOUNTS FOR RENTALS GREATER THAN 14 DAYS.brALSO FOR STAYS OF 4 DAYS MAXIMUM GUEST COUNT IS 6 PEOPLE PLUS $100 CHARGE FOR GOLF CART.brSpend a week on this idyllic Florida island accessible only by boat or ferry- no cars on the island, only golf carts. Free membership to Island Club Olympic sized pool(s), hot tub, free kayaks and bicycles, tennis courts, playground as well as a private deeded access beach all within walking distance from this island home. A short walk (5 minutes) or ride in your golf cart takes you to a private deeded access beach- or to the North Captiva Island Clubhouse facilities. We own the empty lot to our left which gives us a very private and quiet setting. The open floor plan allows the living room and kitchen to flow together – great for cooking and entertaining at the same time! A full wall of glass provides a bright living area and great exposure to the outside. Relax on the screened in porch while the hammock sways you to sleep. The Master and Queen bedrooms each have full private bathrooms and the twin and bunk room share a full bathroom. One additional half bath upstairs.Two bedrooms have TV's and cable access and WiFi is available in the home. An excellent value in this tropical paradise. (Do not purchase damage insurance through VRBO- you will be purchasing this through North Captiva Island Club- $59 for $3000/damage)brAlso if you are a United Mileage Plus member book at- Vrbo/United and get 3x miles.brbrbrbrbrbr

Great Island Retreat- Walk to Beach and Pools

Captiva, Florida, United States

Bed

Bath

Sleeps

$1236.41

Summary:brbrWelcome to the Narrows- Renovated in 2024 this is a private and secluded estate on Captiva Drive, perfect for large gatherings and getaways! This one of a kind Captiva Drive estate aims to please- featuring 5 bedrooms and 5.5 baths across four stories and two wings, a lagoon with oversized pool and bar, and game room.brbrbrbrThe Space:brbrThis incredibly unique home features 5 bedrooms and 5.5 baths across three distinct and sprawling levels. The first level features an expansive game room with pool table, TV, and other assorted games. This room exits directly out to the pool. The garage is located on the opposite side of this level and features three spaces for cars. The second level features a living room and kitchen on the left side and two detached bedrooms on the right side, both of which feature private entrances in the front of the house and can be accessed independently of the main house (great for teens or kids). Both the bedrooms and living room/kitchen have exceptional views of Roosevelt channel and exit out onto back patio with stairs leading down to pool. The third level of this home features three bedrooms, including the master bedroom, all of which feature fantastic views of the Gulf of Mexico and Roosevelt Channel. The third level also features an expansive patio accessible from both the master bedroom and left most guest bedroom upstairs. The master bedroom features an incredibly unique Widow's Walk, providing guests with 360 degree views of the Gulf of Mexico, Roosevelt Channel, and all of Captiva and Sanibel. This is the only Widow's Walk of this height on Captiva and is commonly known to be the very highest point on the island. Be one of the first to experience it following a full top to bottom reconstruction, encompassing nearly two years of work (completed in February of 2024). The house also features a kayak launch area and a private dock. Last but certainly not least, the house features a large heated lagoon style pool amidst a private tropical landscape in the back.brbrbrbrGuest Access:brbrGuests can use the following amenities-brbrbrbr1) Entire main housebrbr2) Three car garagebrbr3) Private pool and patio barbrbr4) Private canoe and kayak launching areabrbr5) Game room- Pool table, TV, ping pong, etc.brbr6) LED living room TV with streaming services and 1400+ channelsbrbr7) 5 bedrooms and 5 baths, plus outdoor pool bathbrbr8) Private beach accessbrbr9) Private dockbrbrbrbrThe Neighborhood:brbrHomes on Captiva Drive are extremely unique and few and far between, with only a handful of homes existing on this prestigious avenue. It is directly on Turner Beach/Blind Pass, and occupies over an acre of beach to bay property.brbrbrbrGetting Around:brbrUber can bring guests to the home from RSW airport.brbrbrbrOther Things to Note:brbrGuests must complete a rental agreementbrbrA non-refundable cancellation fee of $100 will apply for reservations cancelled prior to the cancellation policy window. This fee covers our credit card processing fees on a refunded deposit payment.brbrbrbrInteraction with Guests:brbrWe provide guests with as much privacy as they would like, yet are available in an instant as needed to address any issues, large or small. We are available through phone, text, e-mail, and in person any time assistance is needed and are equipped to handle any guest request.

The Narrows- Stunning Bayfront Villa on Captiva

Captiva, Florida, United States

Bed

Bath

Sleeps

$413.77

*****GOLF CART WITH RENTAL*****br ***** UPGRADED WIFI SPEED *****brWinterhavenbr Oyster Shell DrivebrNorth Captiva Island, FloridabrNORTH CAPTIVA ISLANDbrbrThank you for inquiring about Winterhaven bounded by the Gulf ofbrMexico on one side and Pine Island Sound on the other. We are on abrbarrier island just west of Fort Myers, Florida. We're 500 acres ofbrstate wildlife preserve ... offering world renown shelling, brsubtropical foliage and trees, a look at over 100 species ofbrmigrating nesting birds as well as endangered marine life. brDolphins and manatee play off our shores on this private island. We havebrneither public boat docks or public facilities. There are no bridgesbrto connect us to the mainland. We are a vanishing breed, one of thebrlast true out islands in the United States. We have 4 miles of thebrmost beautiful, serene beaches to be found anywhere on this earth.brbrTHE WINTERHAVENbrJust one minute from the beach, our fully-furnished home offers uniquebrinverted style living. The first floor, set on top of 10 foot brpilings has 2/3 bedrooms, 2 screened-in porches and 2 baths. On the secondbrfloor you will find a spacious living and dining area with cathedralbrceiling. 12 feet of sliding glass doors and windowsbr allows access to anbrexpansive sun deck. brbrLiving Room/Kitchen/Dining Roombr-Full size appliances including stove, refrigerator with ice brmaker, dishwasher, microwave, toaster, blender, coffee maker, telephone, washer and dryer.br-stereo system and ROKU.TV / DVD. Netflix Amazon Video Local TVbr-Dining room seating for 6 and kitchen island seats 2.brbrMaster Bedroombr- large master bedroom with lounging area that broffers full size sofa, table and reading lamp.br-Queen size bed.br-Private bathroom.br-Ample closet room.br-Screened-in porch attached.brROKU.TV /. Netflix Amazon Video Local TV / WIFI provided at our home / Safety Harbor Clubhouse Pool Free WIFIbrbrSecond Bedroombr-One twin size trundle bed - converts to another 2nd bedbr-One additional twin size bed.br-Ample Closet room.br-Screened-in porch attached.brTV/Local StationsbrbrThird sleeping areabr-Lounging area of master bedroom converts into a third bedroom bybrmeans of a moveable wall allowing use of a full size sleeper brsofa.brbrOne of the beautiful features of this island is that no motorbrvehicles are allowed. br *****VERY IMPORTANT*****. brTransportation on the island is an electric golf cart for up to Four ADULTS ONLY or TWO ADULTS and THREE SMALL children(under the age of 10). Any additional people, other than what is stated above, guest will need to rent an additional golf cart. brbr NOTICE: REQUIRED BY OWNER !brYOU MUST HAVE A VALID DRIVERS LICENSE TO OPERATE THIS GOLF CART. Of course, you can always use the oldest form of transportation - foot power.brbr GETTING TO NORTH CAPTIVAbrFly into Fort Myers ... take a cab or rent a car to Pineland Marinabron Pine Island. Before you leave home call the management company. brTell them what time your plane arrives and they will tell you where brtobrstop for provisions on the way to the water taxi. At the dock you brwill be greeted by a representative of thebrmanagement company who will transport your luggage and brprovisions to the house. brbr WHAT ABOUT FOOD brOur home has a fully equipped kitchen. Best to bring your ownbrprovisions ... cook at home ... life is casual. There are 3brrestaurants on the island and a Tiki Bar that offer casual dining for breakfast,brlunch and dinner and a general store for necessities. For yourbrconvenience,.Food Delivery service to pre stock your provisions is available from the following people:Antoine 239-207-6048, Debbie 239-822-7078, brSarah 307-251-7043brbrARE THERE MEDICAL FACILITIES brWe have full time ems /fire stationbrbrISLAND ACTIVITIESbrAs a Safety Harbor Club Member, you have use of a heated pool, tennisbrcourts, clubhouse, snack bar, bird watching towers and private brdocking. Other additional activities included ... shelling,brjogging paths, sailing, fishing and hiking.brArrangements can be made for water taxi excursions to many of thebrnearby islands for dining, shopping and golfing. Boat rental brthroughbrseveral area marinas is available if you wish to explore on your brown.brScheduled water shuttles run daily, reservations required.brbrCARE OF OUR HOUSEbrWe ask that you treat our house gently. Should anything go wrong,brcall the management office. They are available 24 hours a day. brShould anything spill that you feel might stain, call them right awaybrand they will tend to the problem. We do not provide daily maidbrservice unless you request it. There will be an additional charge brforbrthat..

Budget Friendly Island Beach House/60 Second Walk to 4 Miles of Awesome Beaches

Captiva, Florida, United States

Bed

Bath

Sleeps

$564.35

Just By Chance is a newly renovated elevated home with lush tropical landscaping, offering a luxurious and comfortable stay. With cathedral ceilings, finely appointed interiors, a screened lanai, a sun deck, and a pergola, this home provides the perfect blend of indoor and outdoor living. The loft adds a touch of charm and provides additional space for relaxation or entertainment.brbrThis incredible Captiva Island vacation rental is located on Dickey Lane near the heart of Captiva Village. It's just a short walk down Laika Lane to the gorgeous beach, shops, restaurants, and watersports. If you're looking for an unforgettable island vacation, stay at this fabulous Royal Shell home and leave nothing to chance.br brPlease Notebr(1) dog maximum; 35 lbs maximum weight limitbrSleeps 8br7-night minimumbrSmoking is not permitted

Newly Renovated Home on Captiva With a Perfect Blend of Indoor and Outdoor Living

Captiva, Florida, United States

Bed

Bath

Sleeps

$1221.7

*1 Block to the Gorgeous Beach.br*Private heated Pool. br*4 Beach Cruiser Bicyclesbr*Bring a boat or rent one and tie it to our 40' dock, we have plenty of Parking for a Boat trailer br*5 Kayaks br*Golf Cart that seats 6br*2 Master Suites with 3 more En Suites. 7 beds. br*5.5 Bath *WIFI br*Many Board games and puzzles.br*Pool toys *Beach tents, carts & equipment *Beach Fishing cartbr*No penalty for cancellation if a tropical storm arises.brThe spacebr~Included with a 7 night minimum is a FREE 4-hour sightseeing boat tour for 6 people from 10:00-2:00. Get picked at the dock in your backyard and ride to the Island of Cabbage Key and have lunch Or two 2-hour trips without lunch. Maybe see some dolphins with one of the best guides in SW Florida! Details to follow after booking.brbr~One of the best beaches is only a couple minute walk across the street!brbr~The Pool is 4' deep and is heated to around 80-85 degrees. Depending on the outdoor temp it may be above or below that. Please leave the pool gate shut, no diving and there is no lifeguard on duty.brbr~5 Kayaks and lifejackets are also included for free with your stay!brPlease return them to the rack before you leave.brbr~Golf cart is street legal and can be used to tour Captiva or run to a restaurant or shop. It can not leave Captiva. Car seat/booster seat aged children must be in there approved car seat/booster seatbrbr~There are 4 bikes for your use with locks and helmets.brbrLIVING SPACES:brThe open floor plan has plenty of natural light with high ceilings and big sliding windows/doors.br~55 TV with Xfinity cablebr~Wifibr~Enjoy your morning coffee or tea with the great views of the Roosevelt and Wulfert channels on the deck or balcony.brbrMASTER BEDROOMS:br~Bedroom 1 (Crows Nest) is a Master with a King bed and ensuite full bathroom, a walk-in shower and a separate tub.br~Bedroom 2 (The Admiral) is a Master with a King bed and ensuite full bathroom, a walk-in shower and a separate tub.br~Both have 55' TV's with cable.brbrOTHER BEDROOMS:br~Bedroom 3 (The Cove) is a King bed with an ensuite full bathroom tub/shower.br~Bedroom 4 (Light House) is a Queen bed with an ensuite full bathroom tub/shower.br~Bedroom 5 (Sand Dollar) has two twin beds that can be converted to a King. Also has an ensuite full bathroom with walk in shower.br~All have 40 TV's with cable.brbrGame Roombr~A game area with multicade arcade table and has a 32 TV.brbrKITCHEN:br~Fully equipped kitchen w/modern appliancesbr~Seasoning/spices along with cooking spraybr~2 Dining tables that seat a total of 16 peoplebr~Gas grill w/utensilsbr~Ice makerbr~Beverage fridgebr~Keurig and drip coffee makerbr~Nespresso machine for that little extra boostbr~Washer/dryer at the end of the hallwaybr~ The game closet it is at the end of the hallway across from the laundry room.brbrThe outdoor deck is the perfect spot for enjoying the beauty of the Channel, with enough space for guests to relax and soak up the sun and peaceful surroundings.brbrHakuna Matata provides guests with a comfortable and spacious space, perfect for creating lasting memories with loved ones.brGuest accessbrYou will have full access to the house and garage except for the back of the Master closet and the third bay of the garage will be yours to use while you are here.brYou will be given a specific door code for self-check-in.brbr-There is Wifi at the house.brbr-Bookings need to be from Saturday to SaturdaybrbrOther things to note:br~A rental agreement and waiver for the kayaks, golf cart, bikes and pool will need to be signed after booking.br~Booking guest must be 21 years of age or older. Any guest under the age of 21 must be accompanied by a responsible adult.br~No smoking indoorsbr~No petsbr~We provide a starter pack of toilet paper, paper towels, hand and bar soap, dishwasher pods and laundry pods. You may need to buy more depending on your length of stay.

Private Heated Pool~40' dock~Bring a Boat~Golf cart~Kayaks

Captiva, Florida, United States

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$499.62

Sunset Captiva 26 offers the kind of island living you've been dreaming about—where salt air, sunset strolls, and barefoot luxury come together under one roof.brbrThis beautifully appointed 3-bedroom, 2-bath stilt home sits just moments from Captiva's sugar-white beaches and the charming village. Inside, you'll find open living spaces flowing from the fully equipped kitchen with quartz countertops to airy screened lanais perfect for morning coffee or afternoon naps. Two king bedrooms plus extra sleeping space ensure everyone has room to relax, with Smart TVs and Wi-Fi when needed.brbrDownstairs, beach gear and bikes await your daily adventures—shelling expeditions, poolside lounging, or pedaling through Captiva's sun-dappled streets. The village is an easy walk away, where fresh seafood and legendary Gulf sunsets are all part of the rhythm.brbrThis Captiva Island vacation rental strikes that perfect balance: upscale enough to feel special, laid-back enough to let you truly relax. Come see why guests return year after year.

Sunset Captiva 26 - Welcome to your Captiva Island escape

Captiva, Florida, United States

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$1072.87

A Captiva Classic with Endless Character and Sunset CharmbrStep back in time without sacrificing comfort at Baybarlyn Captiva, a sprawling mid-century modern retreat nestled between the Gulf and the bay. Built in 1953 and lovingly preserved, this 3,000-square-foot home brings together vintage island charm and updated conveniences. With a private beach just across the street and a shared dock on the bay, this home offers the ultimate in Captiva-style living—perfect for family getaways, large gatherings, or peaceful retreats.brbrTimeless Style Meets Island ComfortbrBaybarlyn’s open-concept design is made for memory-making. The original 1950s tile floors, exposed brick fireplace, and enclosed lanai with wood finishes add nostalgic warmth throughout. The spacious living and dining area is furnished for comfort with a large sectional, flat-screen TV, and game-ready setup. The adjoining kitchen includes updated appliances, a coffee bar, tall counters, and ample cabinetry for everything from group dinners to morning pancakes.The main-level queen bedroom has an updated en-suite bath and beach views. A few steps down, you’ll find a cheerful, family-friendly guest room with a queen bed, two twins, a flat-screen TV, and a cozy window seat. Upstairs, the first guest suite offers two double beds and a private bathroom. The second upstairs bedroom features a king-sized bed, private bath, and a screened lanai overlooking the pool—an ideal sunrise coffee spot. The backyard is a private oasis with a 32’ x 16’ heated pool surrounded by tropical landscaping. The shallow wading ledge is perfect for little ones, while in-water ledges offer lounging spots for adults. Two outdoor showers are available to rinse off after a beach day or kayak trip.brbrSpecial Features & AmenitiesbrPrivate Beach Access just across the streetbrShared Dock Access for boating, kayaking, or fishingbrHeated Pool with shallow ledge, lounge areas, and lush landscapingbrFour Bedrooms + Multiple Living Areas ideal for families or groupsbrSmart TV, Xbox, DVD Players, Stereo, & Game ClosetbrHigh-speed Wi-Fi throughoutbrTwo Outdoor Showers and a full-size washer/dryerbrEasy access to Captiva’s shops, restaurants, and marinasbrbrPlan Your Island Escape - Whether you're stargazing from the lanai, shelling on the private beach, or launching a kayak into the back bay, Baybarlyn is your gateway to authentic Captiva Island living. Rich with history, thoughtfully furnished, and steps from both sunrise and sunset views, this is the kind of home where stories are made and traditions begin.brbrKingfisher Vacation Rentals will only book reservations up to 51 weeks in advance.brAll of our properties have contact-free check-ins.

Family Friendly- Captiva Pool Home- Gulf Front- Lasting Memories Made Here !

Captiva, Florida, United States

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$1381.01

UPDATE: We are excited to report that Sunsplashed Villa has been renovated and updated, and is fully re-opened for visitors. We're looking forward to welcoming you back to Captiva Island!brbr Click here for the latest information on reopenings of Captiva and Sanibel restaurants, bars, recreation providers, shops, and other businesses: https://sanibel-captiva.org/open-businesses-in-sanibel-florida/brbrStep into comfortable luxury at Sunsplashed Villa, a 5-bedroom, 5-bath Mediterranean-style beach-block home with a private courtyard pool. Up to 12 family members and friends can sleep comfortably in three master suites and two bedrooms -- and gather in two living rooms, an outdoor elevated terrace, and a spacious poolside veranda. brbrLocated in the heart of tiny Captiva Village, at 11514 Andy Rosse Lane, Sunsplashed Villa is less than a three-minute walk from many restaurants, bars, coffee, ice cream, pizza, a grocery and liquor store, two marinas, and the spectacular bay and beaches of beautiful Captiva Island. brbrSunsplashed Villa is private and secluded, yet in the center of it all. When you walk through the front door, you don't step into a house, but a walled courtyard patio with an inviting pool and multiple sunny, and covered, seating areas. When you step outside, chances are you'll hear the fun sounds of guitars or steel drums on your left from the restaurants of the village, and feel the Gulf breezes on the right from the beach down the block.brbrThe three master suites and two bedrooms are cleverly situated so that everybody has their own space: a secluded top floor king suite, two side-by-side main-floor bedrooms, a pool-level king suite with a den, and a completely separate Terrace Suite with its own kitchenette, bathroom, and private entrance.brbrWe're looking forward to welcoming you to the tropical island village of Captiva, and the comfortable luxury of Sunsplashed Villa. We know you're going to love it as much as we do.

Sunsplashed Villa -- Your own private tropical island resort!

Captiva, Florida, United States

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$904.8

Welcome to Isle Escape, an ocean view retreat! On the end of a quiet sand path & easy access to the gulf beaches. brThe open-concept (high ceiling) living area offers breathtaking, unobstructed ocean views, drawing you straight to the water’s edge. Slide open the expansive glass doors and let the sea breeze sweep through as you soak in the serenity of one of the most secluded and private spots on North Captiva. brThoughtful layout ensures both connection and privacy for every guest. brSome of the highlights include-brbr ️Stunning gulf view br ‍♂️Private poolbr ️5 Comfy bedrooms with attached full bathrooms including bunksbr 2,850 Sq ft of open design living spacebr ️Spacious, modern, fully equipped kitchen br 2 Screened in Decks with fans, speakers, and ocean viewsbr High Speed Starlink Internetbr Island Club pool and hot tub access br 2 sets of washers and dryers br Video games and board games, foosball & cornholebr Whole house generator for uninterrupted power during your staybr brKITCHEN AND DININGbr☕️Four coffee makers (Keurig, French press, nespresso & drip)br Refrigerator and freezer featuring craft ice ball maker (A second full sized refrigerator on 1st level provides extra space for storing food and drinks)br Wine Refrigerator for additional drink storagebr ️Kitchen table seating for 8, counter seating for 8br Reverse osmosis system for the cleanest water you can drink (no hauling water to the island)br Non toxic cookware (Green Pan and Williams Sonoma)brbrSLEEPING ARRANGEMENTS br 4 bedrooms feature King bed with Casper mattress, new linens & duvets, ensuite bathroom with shower or tub (1 bedroom on 2nd floor, 3 bedrooms on 1st floor)br All sleeping areas feature wall mounted 4K Roku TVbr Spacious bunk area features 6 twin beds (1st floor)brbrOUTDOOR SPACEbr ️Rooftop deck with a stunning 360 degree view! br Situated on North Captiva's own private grass runway (Prior Approval is required for landing, and included in rental, if flying in is desired, aviation activities are limited)br You may be lucky enough to catch a small aircraft coming in for a landing br ️Sectional and couch seating on screened in decksbr Propane grill on kitchen levelbr Built in speakers and fans br Two nearly new golf carts for leisurely cruising the islandbr ️Beach towels, chairs, umbrellas brbr***Other things to note***brThere is no road access to North Captiva Island; you will arrive by ferry, private charter or personal boat. Our guest concierge will guide you through the planning, so you can effortlessly enjoy this truly remarkable paradise!brbrContact us now to begin making your vacation dreams a reality!

Million Dollar View! Private Pool, Steps to Beach!

Captiva, Florida, United States

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$1534.79

Captiva Star is a luxury home located on beautiful Wightman Lane in the Village of Captiva. The house has 3600 square feet under air, plus over 2000 square feet of screened porches, decks, and lanais. There's five bedrooms and baths, two laundry areas, a full dining area, and a fully-equipped kitchen.brbrYou have your own tropical retreat in the pool area with a heated salt-water pool with spa, a bar area with a second refrigerator.brbrThe house is within walking distance of all of Captiva's unique restaurants, quaint shops, art galleries, a day spa and the beach is only 300 yards away with direct access off of Wightman Lane.brbrNewly upgraded Kitchen. Upgraded TV's, every room has LED HD Tv, Cable with ALL Channels (Including premium). DVR in 2 rooms + living room. Fastest internet available, 120Mb download speeds. brbrThe House is perfect for a large family, a group of friends or even 5 couples! Default pricing is based on a group size of 12 people or less. There is an additional fee for groups larger than 12. The home can accommodate a maximum group size of 18 persons.brbrThe main living area of the home is a large open area, perfect for gathering and entertaining. The doors open to a large screened porch, expanding the entertainment area.

Large Luxury Near Beach Home On Captiva in the Village. Great for Groups!

Captiva, Florida, United States

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$696.88

*This property is located on North Captiva which is only accessible by ferry or boat. *brbrOur home, Dreamcatcher, is on North Captiva Island. This is a remote barrier island in Lee County in Southwest Florida, located just offshore in the Gulf of Mexico. It lies just north of Captiva Island, separated by a channel called Redfish Pass which was created in a 1921 hurricane. It lies just south of Cayo Costa Island, separated by Captiva Pass. North Captiva Island or Upper Captiva Island is comprised of full time residents and vacation renters. We offer gorgeous sugar sand beaches, an abundance of wildlife and tropical plants and landscape, world class shelling and fishing plus two thirds of the Island are State Preserve perfect for walking trails that lead directly to the Ocean.brbr*Dreamcatcher house has been completely gutted and remodeled after Hurricane Ian. No detail spared! Everything BRAND NEW! Dreamcatcher is located on the southern side of North Captiva, the last street before the beautiful nature preserve. You'll have tons of privacy and be away from the crowds here! When you follow our street on a less than 5 min walk or quick golf cart ride you'll find the best beaches stateside. Our home sits on a large private lot with a beautiful private heated pool (new pool heater & pool pump added in 2025) and lots of outdoor spaces to take in the beautiful island life. Enjoy the custom 5 bedroom house/ 5 bathroom house, with 4 bedrooms with en suite bath. The well designed gourmet kitchen is also a delight to cook in. brbrWhen you arrive on the island, you will be met at the dock and we will get you and your luggage settled into the house, which comes with your own personal golf cart for your island transportation during your stay. Our island has no cars, no traffic, only lushly lined sandy trails and golf carts! The property is a short 5 minute golf cart ride from the dock. 2 golf carts are included with your stay. Only licensed drivers can drive the golf cart. brbrOur house is located on the closest street to the 350 acre nature preserve with its wide vista of palm trees. A beautiful white sugar sand beach is just a short stroll or golf cart ride down the street. Don't miss this very special home.brbrBedrooms/ bathrooms-brbr(Bedrooms 1,2,3 are all on the same floor )brBedroom 1- King bed with private bath/ shower br brbrBedroom 2- King bed with private bath/ showerbrbrBedroom 3- 2 full beds with private bath/ showerbr br brBedroom 4- Queen bed with private bath/ showerbr brbrBedroom 5- 2 queen beds + 2 twin bedsbrbrSleeps 16

Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

Captiva, Florida, United States

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$2290.17

** Caretaker on site in separate house** brbrThe ideal home to experience the best of Captiva. This three-bedroom three-bathroom pool home with a hot tub is updated and spacious. Little Current is located right on the water of Blind Pass. This means the best fishing on the island, amazing views, stunning wildlife, and special memories to be made. Multiple decks with beautiful views, an expansive dock for fishing, tying up a boat, or launching a kayak. Walk into the home to a large sitting room with vaulted ceilings and coastal décor. The updated kitchen features solid surface countertops, new appliances, and everything you need to create an amazing meal. The kitchen is open to the comfortable family room with plenty of seating and a flat-screen TV. The open dining area has seating for four at the table with additional seating for three.brbrThe first guest room has two twin beds and a bright clean décor. The second guest bedroom features a queen bed. The guest bathroom has a shower/tub combination. The large master suite features a king bed, flat-screen TV, and attached bathroom with shower.brbrBeach access is right across the street. Blind Pass Beach has STUNNING sunsets and is world-renowned for its beauty. brbrSpend your days relaxing by the saltwater pool, fishing off the dock, strolling along the beach, or walking to the local restaurants. This is truly a special home that you will not want to miss.brbr2 Kayaks are available for rental for an additional fee of $350 per week please email or call to add this to your reservation. The dock can accommodate a 25-foot boat to be tied up along the inner portion of the dock.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)!

The ideal home to experience the best of Captiva

Captiva, Florida, United States

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