Vacation Rentals By Owner In Captiva, FL

Wake up to sweeping Gulf views and step straight onto the sand from this direct beachfront 1-bedroom, 1-bathroom condo on Captiva Island. Perfect for couples or small families, this Gulf-front getaway offers the ideal blend of relaxation, expansive beachfront, and unforgettable sunsets.brbrWhy guests love this condo:br✔ Direct beach access – just steps from your door to the sandbr✔ Sweeping Gulf views and breathtaking sunsetsbr✔ Heated pool, pickleball & tennis courts on-sitebr✔ Close to Captiva Village dining, shopping & attractionsbrbrStart your mornings with coffee on the private lanai as the waves roll in. Spend your days shelling, swimming, and strolling miles of pristine shoreline. In the evening, unwind as the sky lights up with Captiva’s famous sunsets—right outside your door.brbrInside, the condo is thoughtfully designed for comfort and ease, featuring a fully equipped kitchen, open-concept living area, and a cozy bedroom—perfect for weekend escapes or extended stays.brbrLocated just outside the gates, you’ll find some of Captiva Island’s most popular restaurants, boutiques, and activities nearby—offering the ideal balance of seclusion and convenience.brbrImportant Information:brNestled within a beautifully maintained resort-style gated community, this condo offers a peaceful and private island escape. While access to select resort amenities—such as fitness centers, restaurants, and boat docks—is not included, many guests appreciate the cost savings and more relaxed, uncrowded atmosphere this provides.brbrYou’ll still enjoy fantastic on-site features, including a heated pool, tennis and pickleball courts, and direct beachfront access just steps from your door—giving you everything you need for a memorable and carefree Captiva getaway.brbrWhether you're searching for a Captiva Island vacation rental, Gulf-front condo, romantic beach getaway, or a peaceful island escape, Beach Villa 2322 delivers an exceptional coastal experience.

Captiva Beachfront Condo 2322 | Direct Gulf Front | Pool, Tennis & Pickleball

Captiva, Florida, United States

Bed

Bath

Sleeps

$308.55

Your Captiva Sanctuary with Unforgettable Gulf Panoramas: Beach Villa 2617brbrDiscover pure island bliss at Beach Villa 2617, a beautifully reimagined 1-bedroom, 1-bathroom condominium, thoughtfully situated within the exclusive South Seas Resort community on Captiva Island. Perched on the second floor, this haven offers an unparalleled vantage point, showcasing captivating, unobstructed vistas of the Gulf of Mexico. Designed for ultimate relaxation, it provides a spacious living environment and every comfort needed for your idyllic Captiva escape.brbrHighlights of Your Stay:brGulffront Grandeur: Step onto your private, screened lanai and be instantly enchanted by the sweeping Gulf views. Imagine savoring your morning coffee with the sunrise painting the water, or toasting the sunset with the gentle rhythm of the waves as your soundtrack.brContemporary Comforts: Inside, a recently renovated interior welcomes you with a generously sized living area, appointed with comfortable furnishings – the perfect spot to unwind after a day of island adventures.brCulinary Corner: A fully equipped kitchen awaits your culinary endeavors, complete with all necessary appliances and cookware. Enjoy your homemade delights at the inviting dining table or opt for an al fresco experience on your Gulf-view lanai.brPeaceful Slumber: The primary bedroom offers a tranquil sanctuary featuring a plush king-size bed, ensuring a restful night's sleep, complemented by a convenient full bathroom.brConvenience at Hand: Benefit from easy elevator access to your unit and on-site, pay-per-use laundry facilities. Stay connected with complimentary wireless internet access.brAssociation Amenities: Indulge in a refreshing swim in the heated community pool, challenge a friend on the tennis court (additional fee may apply), or simply bask in the glorious Florida sunshine by the Gulf.brExplore Captiva's Charms: While this private rental does not include access to the broader resort amenities, you'll find an array of delightful local restaurants just beyond the resort gates. Embrace nearby Sanibel's natural splendor at the renowned J.N. Ding Darling National Wildlife Refuge or simply soak in the island's captivating, laid-back atmosphere.brbrImportant Considerations for Your Stay:brThis unit is located on the first floor (one flight up), accessible by elevator.brLaundry facilities are available for guest use on the lower level (coin/card operated).brPlease note that this is a privately managed condo. Guests of this unit do not have access to the full South Seas Island Resort amenities, including the resort's trolley, golf course, and specific resort restaurants located within the main gates.brHowever, you are welcome to enjoy the association pools, tennis courts (fee may apply), BBQ grills, and, of course, the stunning beach. Many wonderful dining and shopping options are conveniently located just outside the resort's entrance.brWhile elevators are typically operational, as mechanical systems, we cannot guarantee their continuous functionality throughout your stay. Refunds will not be issued in the event of an elevator malfunction.brPlease be aware that due to Hurricanes Helene and Milton, access to some amenities within the general area may be limited at the time of your stay.brFor your convenience, we've partnered with VayKLife to enhance your beach experience! This rental does not include beach chairs or umbrellas. Instead, you'll receive a credit to use towards renting essential beach gear like chairs, umbrellas, coolers, and wagons, delivered directly to your door. This allows you to pack lighter and select exactly what you need. A link to redeem your credit will be provided in your booking confirmation.brCurrently, there are no planned construction projects within the immediate South Seas Resort area. However, please be advised that should any unforeseen construction or maintenance occur during your visit, refunds will not be provided for disruptions beyond our control.brbrDon't just dream of paradise – experience it! Book your unforgettable Captiva Island getaway at Beach Villa 2617 today.

Beach Villa 2617: Captiva Island Paradise: Your Direct Gulf-View Villa Awaits

Captiva, Florida, United States

Bed

Bath

Sleeps

$299.42

Summary:brbrTotal relaxation awaits at this wonderfully appointed Marina Villa within South Seas resort. Appointed in a classic coastal style and just a matter of feet from the beach, this residence is the perfect island getaway! Situated on the very northern tip of Captiva, this residence is perched over one of the most sought after views in all of the resort- The Yacht Basin and Marina. Enjoy serenity as you view dolphins and manatees at play from the comfort of your oversized lanai!brbrbrbrThe Space:brbrThis wonderfully appointed Marina Villas residence boasts fantastic amenities and modern finishes, featuring beautiful coastal decor, a bright and airy living and dining area, a comprehensive kitchen, and 2 spacious bedrooms. This property comfortably accommodates a party of 6, featuring a King bed in the master quarters, 2 twin beds in the guest bedroom and a pull out queen sleeper sofa in the living room. brbrbrbrTHIS PROPERTY IS NOT AFFILIATED WITH SOUTH SEAS ISLAND RESORT. RENTAL DOES NOT INCLUDE, AND DOES NOT PROVIDE ACCESS OR ENTITLEMENT, TO ANY SOUTH SEAS AMENITIES..brbrbrbrGuest Access:brbrIncluded in the rental of this unit is the use of the many amenities at the Marina Villas complex, including a heated pool, grill and cooking area, communal laundry room, as well as all South Seas beaches and grounds.brbrbrbr The unit is located within a five minute drive to downtown Captiva Village where one can enjoy great dining and shopping. brbrbrbrAccess to greater resort amenities such as the pool on the opposite end or the South Seas lounge chair area is not included. We provide high-end beach gear that guests can use during their stay. brbrbrbrOur repeat guests prefer staying with us over booking through the resort as you are GUARANTEED the unit you book online, what you see is what you get! Staying with us guarantees you a fantastic unit, access to pools and beaches less than a minute from your room, first-class guest services, and far more economical pricing. brbrbrbrPlease note that there is ongoing construction happening at South Seas related to the addition of new amenities at the entrance to the resort.brbrbrbrThe Neighborhood:brbrMarina Villa 603 is located within the enclave of South Seas Island Resort with white sugar sand beaches and balmy breezes off the turquoise waters of the Gulf of Mexico.brbrbrbrGetting Around:brbrGolf cart recommended.brbrbrbrOther Things to Note:brbrGuests must sign a rental agreement upon booking the property.brbrA 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.

Gorgeous Marina Villas Residence at South Seas

Captiva, Florida, United States

Bed

Bath

Sleeps

$757.79

Welcome to our Captiva Island vacation rental home aptly named Sandy Seas Villa. As soon as you arrive, you will realize how special our vacation home is, being just one home from the sand. With plenty of room for up to 14 guests, your entire family and even some friends and extended family can share the experience for a fun-filled week or longer stay. The main level of the home features a spacious living area with a flat panel TV, a dining room with enough seating for the entire group, and an open kitchen that has everything you'll need to prepare meals and entertain. There are three bedrooms and three and a half bathrooms on the main level as well. Two of the bedrooms have queen beds while the third bedroom has two twin beds. Upstairs is a loft with a sleeper sofa and the master bedroom suite with a king-sized bed and en-suite bathroom with tub and a separate shower. There is a lounging deck off the master bedroom to soak up the sun. Off the main level, there is a wrap-around porch for lounging, relaxing, and reading your favorite book, or just enjoying a cup of coffee and viewing the gulf views. Downstairs is the expansive heated pool and pool area with plenty of seating and an outdoor shower. There's also a private suite with a king bed, a sleeper sofa, a TV, and a full bathroom. We do have a gas BBQ grill if you would like to cook up burgers, dogs, or your favorite BBQ. Beach towels are provided, and beach equipment is available through our partnership with VayKLife—so all you need to bring is yourselves! Be sure to re-book your stay and enjoy your vacation home away from home year after year.brPlus, we’ve recently added a brand-new hot tub to the beautiful pool area for even more relaxation during your stay.brbrImportant 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 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.***br

Sandy Seas Villa - Just one home from the Sand

Captiva, Florida, United States

Bed

Bath

14

Sleeps

$575.62

Summary:brbrWelcome to 2531 Beach Villas- New to our program, this residence is an executive caliber vacation rental featuring three bedrooms and three baths, situated across more than 1,500 square feet of living space! For those discerning guests seeking a premier beachfront experience, look no further than 2531 Beach Villas! Featuring sleeping capacity of up to 8 guests, vaulted cedar ceilings, and a large loft, guests will revel in the privacy this unit affords them. This residence is also amenity rich, featuring a large heated pool, pickleball and tennis courts, high-speed Wi-Fi, and outdoor grills.brbrbrbrThe Space:brbrYour Ultimate Beachfront Escape Awaits!brbrWelcome to your dream Gulf Front Villa—where luxury meets the serene beauty of the sea. Freshly renovated from top to bottom, this stunning villa offers the perfect retreat for those seeking comfort, style, and unforgettable views. With three spacious bedrooms, three full bathrooms, and a versatile open loft, there’s room for the whole group to relax and unwind. And the best part The breathtaking Gulf of Mexico is right outside your window!brbrbrbrInside Your Private ParadisebrbrWhether you're cooking, relaxing, or entertaining, this villa delivers the perfect setting. The fully equipped open kitchen makes meal prep a breeze, while the living and dining areas invite you to kick back and take in the panoramic ocean views. Step out onto the expansive lanai—ideal for enjoying your morning coffee, evening cocktails, or simply listening to the calming waves.brbrbrbrSleeping arrangements are designed with comfort in mind brbrA luxurious king master suite and guest bedroom with two twin beds on the first floor, plus an additional queen bedroom and open loft on the second floor. There is also a brand queen new sleeper sofa in the living room. It's a warm and inviting space for families or groups craving a beach-inspired escape. brbrbrbrAdventure & Relaxation at Your FingertipsbrbrWhen you're ready to explore, step outside for a beach day filled with sun, sand, and shell hunting along Captiva Island’s pristine coastline. Prefer a dip in the heated pool It’s just steps away. Discover charming island boutiques, browse local art galleries, or savor fresh seafood nearby. For outdoor fun, fire up the grills, rent bikes or golf carts, or set sail on a dolphin-watching cruise with Captiva Cruises. Feeling adventurous Go parasailing, jet skiing, or rent a kayak for a scenic paddle.brbrbrbrEasy & Effortless BookingbrbrBooking your stay is seamless with Rosen Vacations. We offer keyless check in using an entry code, arrive at your convenience, settle in, and let the relaxation begin.brbrbrbrGuest Access:brbrIncluded in the rental of this unit is the use of the many amenities at the Beach Villas complex, including a heated pool, tennis courts, grill and cooking area, and a communal laundry room. The unit is located within a five minute walk to downtown Captiva Village where one can enjoy great dining and shopping. We provide high-end beach gear that guests can use during their stay. Our repeat guests prefer staying with us over booking through the resort as you are GUARANTEED the unit you book online, what you see is what you get! Staying with us guarantees you a fantastic unit, access to pools and beaches less than a minute from your room, first-class guest services, and far more economical pricing.brbrbrbrTHIS PROPERTY IS NOT AFFILIATED WITH SOUTH SEAS ISLAND RESORT. RENTAL DOES NOT INCLUDE, AND DOES NOT PROVIDE ACCESS OR ENTITLEMENT, TO ANY SOUTH SEAS AMENITIES..brbrbrbrThe Neighborhood:brbrThe unit is located within the Beach Villas complex and it is located on the gulf side, close to both the beach and downtown Captiva.brbrbrbrGetting Around:brbrThe best way to get around on Captiva is a golf cart, or on bikes. You can Uber from RSW Airport for just $50-70 and really will not require a car while here unless planning to visit Sanibel and neighboring areas.brbrbrbrOther Things to Note:brbrWe require guests to complete a rental agreement prior to checking in. The agreement will be sent upon booking confirmation. brbr A 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 are available as often as needed, but provide guests the privacy the desire to enjoy their vacation in peace!

2531 Beach Villas - Executive Captiva Penthouse

Captiva, Florida, United States

Bed

Bath

Sleeps

$339.76

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

Quiet, clean townhouse. Relaxing winner. Harbor view, short Gulf walk…

Captiva, Florida, United States

Bed

2

Bath

6

Sleeps

$437.11

The Lucky Pelican is our family’s 4 br /2 bath, spacious home with coastal-inspiredbrinterior design and wonderful outdoor spaces as well. The Lucky Pelican was freshly updatedbrin 2026, with Crate & Barrel furnishings and design, new appliances and new outdoor seating areas in the front, side and rear of the home. Located on popular Wightman Lanebron beautiful Captiva Island, it is an enjoyable three minute (254 steps) walk down thebrsandy lane to the beach and Captiva’s famous shells, warm Gulf waters, aquatic wildlifebrand of course, the glorious Captiva sunsets and The Mucky Duck.brbrAfter staying at this home as guests of the prior owner (Rick’s Retreat) in 2019, our familybrwas thrilled to take on bringing it back to life in 2025 following Captiva’s weather eventsbrin the prior year. We were able to enjoy the property as a family for the holidays in 2025brand now we have begun offering the Lucky Pelican for weekly rentals. Our home offers a calm, tranquil interior and versatile indoor/outdoor spaces to fully enjoy Captiva. Lucky Pelican is perfect for couples, families or friend groups and sleeps up to 8 comfortably.brbrThe Lucky Pelican offers tropical landscaping and natural privacy and is set back off ofbrthe quiet private Wightman Lane (only resident vehicles are permitted). The exterior of our home is intended to provide morning and evening enjoyment while supporting beach trips, outdoor grilling, and relaxation. We have a shell stone dedicated parking area for two vehicles off of Wightman Lane. Our front patio has new white tile and modern comfortable outdoor seating with a large coffee table making outdoor coffee, cocktails or informalbrdining enjoyable. Just off this tile patio, there is an open outdoor exterior shower and/or foot shower for your convenience. A few steps away there is also an exterior beach shed stocked with chairs, an umbrella and assorted beach toys for your use.brbrThe heart of the home is built around an open floor plan with a combined family room, dining room and kitchen concept. The layout keeps things breezy and bright, with windows and glass doors combining to create a relaxing atmosphere. The family room has a new 85” television and plenty of board games surrounded by ample seating with a large couch and multiple comfortable chairs. The updated kitchen offers sunny blue tilework, new top-quality appliances and fun amenities which include a pebble ice-maker and a Ninja SLUSHi (recipe book provided).brbrThere are four bedrooms in our home, with the Primary Bedroom being located in thebrrear of the house with a private lanai accessible from the room. The Primary Bedroombrhas a king bed and a large walk-in closet, and through the sliding glass doors you enterbrthe lanai which offers a wonderful and private fully screened in space that contains twobrchairs and a small table. The primary bathroom has a shower and tub.brbrThe second bedroom has a queen bed and bright light from multiple windows. The thirdbrbedroom has two twin beds with a cheerful décor and design. The fourth bedroom has abrqueen bed and a wall of light leading out to a side patio. The sliding glass doors let youbrenjoy this patio for two that is a perfect spot for a morning coffee, an evening glass of wine,bror just a moment to take a break.brbrWe also have a full sized washer and dryer.brbrOne of our favorite things about the location of our Lucky Pelican is its proximity to some amazing restaurants and amenities on Captiva, allowing you to park your car and forget about it for your stay. The Mucky Duck, Cantina Captiva, Keylime Bistro, The Green Flash, the Bubble Room, Starbucks, and more are all within a five minute walk. Just around the corner is The Island Store, a small grocery store for any last minute items you might need, and a coffee and ice cream shop sits at the end of our street at Boop’s Ice Cream Parlor & Cafe. brbrA short drive away by car to nearby Sanibel allows you to take in more amazing beaches and shelling or visit the J.N. “Ding” Darling National Wildlife Refuge. And finally, we cannot say enough about the sunset tradition on Captiva, where so many island residents make their way to saybrgoodbye to the sun each day, and to enjoy the camaraderie of the island.

Heart of Captiva 4BR home; private sandy lane 254 steps to beach, restaurants!

Captiva, Florida, United States

Bed

Bath

Sleeps

$394.33

Actual review left by a Guestbr“We had a great time in Captiva Island. It's the perfect place to get away for a relaxing, secluded, car-free vacation. Federico's cottage is conveniently located just a short walk to the beach and had all of the amenities we needed to relax and enjoy the trip. Federico was helpful and responsive when I had any questions. I highly recommend staying here if you are looking to disconnect and enjoy pristine beaches with lots wildlife and natural beauty. ”

“Coral Cottage”
A Cottage Secluded in Palms with a Jacuzzi 2 minute walk 2 Beach

Captiva, Florida, United States

Bed

Bath

Sleeps

$303.08

Summary:brbrGorgeous Bayside Villa unit featuring panoramic bay views, plush master quarters overlooking the water, ample living room space with Queen sized pullout sofa and twin XL fold out Murphy bed, able to comfortably accommodate parties of 5. Extensive renovations over the past year have created a beautiful, family friendly vacation villa without compromising modern amenities and comfort.brbrbrbrThe Space:brbrThis villa is located on the first floor and boasts 850 square feet of optimized island living space. Making this unit truly unique is its waterfront disposition featuring bay views from both the lanai and master bedroom, wake up in the morning to the sound of wildlife. The owner had a very unique and space-conscious Twin XL sized murphy bed installed under the TV in the living room, making this unit probably the only one that can comfortably sleep a party of 5 in the Bayside Villas of South Seas. The kitchen is outfitted with top of the line kitchenware and the unit comes with a variety of beach gear.brbrbrbrGuest Access:brbrIncluded in the rental of this unit is the use of the many amenities at the Bayside Villas complex, including a heated pool, spa, grill and cooking area, and a communal laundry room. The unit is located within a ten minute walk to downtown Captiva Village where one can enjoy great dining and shopping. Our repeat guests prefer staying with us over booking through the resort as you are GUARANTEED the unit you book online, what you see is what you get! Staying with us guarantees you a fantastic unit, access to pools and beaches just a few minutes from your room, first-class guest services, and far more economical pricing. brbrbrbrTHIS PROPERTY IS NOT AFFILIATED WITH SOUTH SEAS ISLAND RESORT. RENTAL DOES NOT INCLUDE, AND DOES NOT PROVIDE ACCESS OR ENTITLEMENT, TO ANY SOUTH SEAS AMENITIES..brbrbrbrThe Neighborhood:brbrThe unit is located only a matter of feet from the beach, allowing guests to enjoy either the tranquility and hidden beauty of the bayside or the wonder any of the esteemed Captiva beaches surroundings in style whether by bikes or on foot with the beach cart.brbrbrbrGetting Around:brbrWe recommend using golf carts and bikes to get around Captiva.brbrbrbrOther Things to Note:brbrGuests will be required to sign a rental agreement prior to checking in. brbrA 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.

Gorgeous Bayside Residence, Sleeps 5

Captiva, Florida, United States

1

Bed

2

Bath

Sleeps

$983.24

Spectacular Sunsets. Private multilevel designer home with heated pool and spabrMultilevel Designer Home with plenty of room for family. Multiple living areas and plenty of outside areas to enjoy. The home has amazing Sunrise and Sunset views. Walk or take the golf cart to the beaches or relax in the private heated pool with an overflow spa. In addition, expanded lot with plenty of outdoor space to enjoy!!brbrNo Plans III is a luxury 2700 square-foot beach house with a private pool and 2 golf carts!!!brbrEnjoy No Plans III, an architectural delight providing a standard of living second to none. This lovely beach-view home has no shortage of quality and award-winning elegance. The designers of this beautiful home intentionally named this model, The Deck House, providing numerous decks off every level. The combination of interior elegance and exterior delight blend together seamlessly as it was always meant to bebrbrAs you enter into the No Plans III beach house you will be taken away by the combination of elegance and comfort visualizing the beautiful living room furnishings and décor. Truly a delight. This high standard of living is well complemented by an abundance of open space for entertaining. Leather couches and love seats and Old Florida-style paddle fans throughout.brbrOn the upper level is a lovely gourmet kitchen with top-of-the-line appliances, an RO system, an ICE maker, and much more. A formal dining room with glass windows from floor to ceiling for dramatic views of the emerald waters of the Gulf of Mexico. Multiple living rooms can be found on the 1st and 2nd floor for more entertaining and offer additional sleeping capacity with 3 pullout beds.brbrThe 3 large bedrooms are lavishly furnished and equipped. A 4th sleeping/bed area is on the 3rd level in the Sky lounge crew nest for peace and tranquility with a panoramic view of the Gulf of Mexico and Island scenery.brbrWelcome to No Plans III!brCheck in after 4:00 PMbrMinimum age to rent: 30brCheck out before 9:00 AMbrChildren allowed: ages 0-17brNo events allowedbrSmoking is not permittedbrNo pets allowed

No Plans III. Spectacular Sunsets. Private multilevel designer home with heated pool and spa

Captiva, Florida, United States

Bed

Bath

$654.26

☀️ Osprey`s Nest | Relaxing Coastal Pool Retreat | Sleeps 6 - Includes a Sunset Cruise for all guestbrNorth Captiva is Only accessible by boat or small plane- renting this property will Include your travel ferry tickets. br Welcome to Osprey`s Nest—a bright and breezy 3-bedroom, 2-bathroom pool home just minutes from the ocean. Perfect for families or friends looking for a laid-back escape, this stylish retreat offers comfort, space, and all the coastal vibes you need for the ultimate getaway. What You’ll Love: • Private pool & rooftop deck for sunset views • Family-friendly layout with room for 6 guests • Just a short drive to beaches, shops, and restaurants • Fully equipped kitchen & outdoor grill for home-cooked meals • Pet-friendly (on request!)—so bring your furry friends along Sleeping Arrangements: • Bedroom 1: King bed, private bathroom, smart TV, and large closet • Bedroom 2: Two twin beds + smart TV • Bedroom 3: Queen bed with balcony access & rooftop deck entry Bathrooms: • Master ensuite with walk-in shower • Shared bathroom with a tub—great for kids Cook, Chill, Repeat Our modern kitchen is fully stocked with everything you need—coffee makers (yes, plural!), blender, toaster, spices, and even wine glasses for your sunset toasts. Enjoy meals indoors or out by the pool. Work & Stream Ready Fast WiFi, smart TVs in key rooms, and a laptop-friendly desk make remote work a breeze. Outdoor Fun Lounge by the private pool, fire up the BBQ grill, or catch the ocean breeze from the rooftop deck. Pet-Friendly We welcome well-behaved pets on request. Let us know if you’d like to bring your four-legged family member. Easy Parking & Access Free parking available. Entire home is yours—no shared spaces.

☀️ Osprey`s Nest | Relaxing Coastal Pool Retreat | Sunset Cruise & Ferry Travel Included

Captiva, Florida, United States

Bed

2

Bath

6

Sleeps

$694.12

Welcome to your private island retreat on North Captiva Island! This stunning 3-bedroom, 3-bathroom home offers the perfect blend of comfort and luxury, complete with a private pool, hot tub, and spacious outdoor seating area to soak in the island breeze.brbr The Space:brbr3 Bedrooms, 4 Beds – Sleeps up to 8 guestsbrbr3 Bathrooms – Modern and well-equippedbrbrPrivate Pool & Hot Tub – Relax and unwind in your tropical oasisbrbrOutdoor Lounge & Dining Area – Perfect for morning coffee or sunset cocktailsbrbrGolf Cart Included with home!brbrLocated within walking distance to the beach, Island Club, and Nature Preserve, Smugglers Hideaway provides easy access to North Captiva`s pristine attractions. As Island Club members, guests enjoy pools, hot tub, bikes, kayaks, paddle boards, and more. Travel by golf cart or bicycle on sandy native trails, as the island offers no cars or paved roads. brbrExperience the charm of `Old Florida` with just enough amenities to suit your needs. Smugglers Hideaway is fully equipped with resort-style luxuries, including beach towels, spices, and coffee. The island`s peaceful ambiance and natural beauty provide the perfect backdrop for shelling, fishing, and bird watching. brbrAccess the island by ferry, private boat, or small plane, with the nearest airport in Fort Myers. Be sure to stock up on supplies, as local amenities are limited. Embrace a slower pace and create unforgettable memories at Smugglers Hideaway where relaxation and adventure await.brbrWhether you`re here for a family vacation, romantic getaway, or adventure with friends, this home has everything you need for an unforgettable stay. Book now and experience the magic of island living! ☀️ ️

Smugglers Hideaway - Private Pool & Hot Tub

Captiva, Florida, United States

Bed

Bath

8

Sleeps

$4297.72

Welcome to Mangrove Manor, a premier waterfront estate located directly on the Pine Island Sound beach on North Captiva Island. This expansive home offers breathtaking sunrise and sunset views, nearly 360-degree island and water vistas from multiple levels, and direct access to your own private beach just steps from the front door.brbrProfessionally hosted as an Admiral Home by The Island Club, Mangrove Manor is designed for large families, multi-family vacations, and group gatherings seeking luxury, space, and unforgettable island scenery. Guests can relax by the private pool and spa, enjoy wildlife viewing from the dock, or gather across the home’s multiple indoor and outdoor living areas.brbrTHE SPACEbrbr5 Bedrooms | 5+ Bathrooms | Sleeps up to 19brbrPRIMARY MASTER SUITE (SECOND FLOOR)brbrKing-size bed with six large pillowsbrbrLuxurious en-suite bathroom with walk-in stone shower and soaking tubbrbrPeaceful private retreat with water viewsbrbrQUEEN BEDROOMSbrbrThree queen-size beds with pillows and linens providedbrbrComfortable and private sleeping spaces ideal for couples or adult guestsbrbrBUNK AND FLEX SLEEPING AREAbrbrFour full-size bedsbrbrOne twin-size bedbrbrGreat setup for children, teens, or flexible group sleepingbrbrADDITIONAL SLEEPING OPTIONSbrbrTwo full/queen-size sleeper sofasbrbrIdeal for extended family or overflow guestsbrbrLIVING AND GATHERING AREASbrbrMultiple living rooms across levelsbrbrElevator access to all floorsbrbrTwo full bars for entertainingbrbrKITCHEN AND DININGbrbrGourmet kitchen with gas rangebrbrFully equipped for large-group meals and gatheringsbrbrOUTDOOR LIVINGbrbrPrivate pool and spabrbrPrivate boat dock with seatingbrbrExcellent wildlife viewing, including dolphins and ospreybrbrDirect private beach access just steps from the homebrbrIf you have questions about layout or sleeping arrangements, our team is happy to assist.brbrPROPERTY ACCESSbrbrGuests enjoy full private access to the entire home, including all interior living spaces, elevator, private pool and spa, dock, outdoor areas, and private beach access.brbrOne golf cart is included with your stay for convenient island transportation.brbrGuests also enjoy full access to Island Club amenities, including:brbrTwo swimming 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 questions, dock usage guidance, and personalized local recommendations.brbrNEIGHBORHOOD OVERVIEWbrbrMangrove Manor is located on North Captiva Island, a secluded, car-free barrier island known for pristine beaches, abundant wildlife, and relaxed Old Florida charm.brbrThis Pine Island Sound–front setting offers calm waters ideal for boating, kayaking, fishing, and wildlife viewing, while remaining close to open Gulf beaches.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.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.brbrAdditional Notes:brbrPrivate boat dock available for guest usebrbrElevator access to all floorsbrbrPlease stock up on groceries and essentials before arrival or arrange deliverybrbrHouse Rules:brbrNo pets permittedbrbrNo 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

5BR North Captiva Estate Sleeps 19 with Pool & Dock

Captiva, Florida, United States

Bath

17

Sleeps

Exceptional(8)

Select Dates for Price

Captiva Paradise. Privately owned premier corner location one-bedroom, two bath Bayside Villa with beautiful lanai view of the marina and pool. Step outside for a Short walk to the fabulous beach and village of Captiva. Enjoy mesmerizing sunsets, beach walks and large pool. Open floor plan with spacious living, dining area, large waterfront lanai, kitchen with breakfast island and roomy bedroom with ensuite bathroom. See other things to note for resort access info.brbrRecently updated after hurricane Ian including brand new stainless kitchen appliances, new guest bathroom, updated master bathroom, new lanai furniture and freshly painted throughout. Very comfortable king bed in master bedroom with ensuite and walk-in shower. Second full bathroom for guests. Extremely comfortable pull-out queen sofa bed in living room. 55 flat screen, smart TV in the living room and 50” flat screen, smart TV in the master bedroom; both with cable. Everything you need in the kitchen for cooking meals and towels, chairs and umbrella for the beach and more! Outdoor grilling available poolside. Use the Clean Cash App for laundry available on the first level - no coins are needed but coins can be used.brbrOther things to note:brOur condo is a private residence within the South Seas Island Resort. Amenities included are the large Bayside Villas heated pool, hot tub, BBQ grills, free on-site parking, Bayside marina access (for small fee), beach chairs & umbrellas provided by us. The following resort amenities are NOT included: golf course, resort designated beach chairs, north end pool complex, Tiki bar or resort only restaurants on the north end of the island. Our condo is a perfect LOCATION within walking distance to the quaint Captiva Village with numerous restaurants/cafes and shops. The beautiful beach is a short walk (about 8 minutes) and we provide beach towels, chairs and umbrellas. There are no private beaches so you can put up your beach umbrella and chairs anywhere on the beach you desire! For a fun experience to cruise around the island consider renting a golf cart. Our kitchen is fully equipped with new stainless appliances, including a Keurig coffee maker. If you intend to cook your own meals, a suggestion would be to purchase groceries before you arrive and utilize the local stores for miscellaneous grocery items as needed. Royal Shell is our property manager and communicates via email with you for check in instructions prior to your arrival. Your arrival packet can be picked up, on and off business hours, at the Royal Shell Sanibel lsland location (en route to Captiva). Royal Shell has an office on Captiva for any questions though out your stay or you can call them at anytime as well.

Captiva Sweet Retreat at 4124 Bayside Villas

Captiva, Florida, United States

Bed

Bath

Sleeps

$1275.75

Welcome to Gulf Swells & Sea Shells – your ultimate oceanfront haven! Completely renovated, this stunning Large, 5-bedroom, 5-bathroom pool home offers an expansive 2,560 square feet of pure comfort and elegance. Unlike other rentals, our home grants you genuine actual oceanfront views from within, so you won't miss a single moment of the breathtaking scenery. Leave your worries behind as you relish direct beach access right from the property – no need for carts! Say goodbye to endless stair climbs; here, ocean vistas grace the kitchen, living, and master bedroom areas. With a private heated pool and serene screened decks, every second promises relaxation. Immerse yourself in the tranquil symphony of the ocean's soothing waters. Your extraordinary oceanfront escape awaits!brbrGulf Swells & Sea Shells presents a reverse floor plan with four bedrooms, three baths, and a laundry room on the main level. The second floor boasts a full bath, all new kitchen appliances and furniture with beautiful views of the ocean. It is the perfect backdrop as your friends and family gather together. The fully remodeled master bedroom is located off the great room and features a king-sized bed complete with Gulf views for your viewing pleasure. brbrIncluded with your rental of Gulf Swells & Sea Shells:br- One 4-seat golf cartbr- Newly remodeled Kitchenbr- Bedding and linensbr- Bath and Beach towelsbr- Beach cart, and 4 chairsbr- Garbage bagsbr- Iron and ironing boardbr- A basic supply of Shampoo, toilet and facial tissuesbr- Paper towelsbr- Soap (hand, kitchen, dishwasher, and laundry)br-Gas Grillbr-Pinball machine accepts quarters and dollar billsbr-Ping Pong Tablebr-Corn HolebrbrNot included with your rental:br- Transportation to and from the airportbr- Water taxi to and from North Captiva Islandbr- Food, beverages, seasonings, storage bags, shampoo, and body soapbrbrDue to local wildlife ordinances we ask that you turn off exterior lighting at night when not in use outdoors. For this reason and for your security we have placed 7 exterior blink cameras outside the home. They are motion activated and located above the front steps to cover property entrance and golf cart, one located on the NE upper corner of the front porch to cover front door, porch steps and porch entry, up high attached to fascia on the south east corner of the home covers east side of property, water tanks and ac units, one located under the house by facing SW to cover storage area, Garage and utilities under the home and 3 cameras located on the roof fascia points facing the NE section of the lot the NW sections of the lot and the SW sections of the lot. No cameras are pointed directly into the pool. There are no cameras located inside the home. Cameras are for your security. Please note patio doors in the master bedroom to the exterior decks are locked for guest safety.

Luxury Beach Escape, Private Pool, Golf Cart Included, Limited Spring Dates!

Captiva, Florida, United States

Bed

Bath

Sleeps

$446.97

Welcome to your perfect Island escape! This beautifully updated 3-bedroom, 3-bath Bayside Villa penthouse, located near South Seas, offers everything you need for a relaxing and memorable getaway. With the largest floor plan in Bayside Villas, this spacious two-story condo provides plenty of room for your family to unwind and reconnect—all while enjoying stunning views of the Roosevelt Channel and Pine Island Sound.brbrStep onto your private screened lanai and watch boats drift by, dolphins play, and seabirds glide across the water. Inside, you’ll find a full kitchen, comfortable living area, and three inviting bedrooms—each with its own private bath. The master suite features a king bed and breathtaking bay views, the second bedroom offers a bright setting with another king bed, and the third bedroom includes two double beds perfect for families or friends.brbrThe beach is just a short walk away, and you’re ideally located near the entrance of South Seas for easy access to Captiva’s shops, restaurants, live music, art galleries, and all the fun of island life.brbrWhile you won’t have access to resort amenities, your Bayside Villa comes with plenty of its own perks: a large heated pool, high-speed Wi-Fi, outdoor grills, community washer/dryers (coin-operated), beach chairs and towels, and—of course—the beach just steps away. Golf cart rentals are available nearby (electric carts only within the gates).brbr*Please be aware that there is ongoing construction throughout the resort*brbrKingfisher Vacations will only book reservations up to 51 weeks in advance.brAll our properties offer contact-free check-in—no office stops and no stoplights on Captiva!

Bayside Villa 5344- Stunning Direct Bay Views- Heated Pool

Captiva, Florida, United States

Bed

Bath

Sleeps

$320.13

brNestled at the conclusion of a tranquil lane lies Calliope Cottage, a snug and well-appointed bungalow offering optimal seclusion in a meticulously crafted 2-bedroom residence. Ideal for those yearning for privacy, this retreat is just a brief stroll from the unspoiled beach. Embrace the serene ambiance with no cars or bustling crowds, providing an idyllic escape reminiscent of a bygone era on North Captiva Island. Experience the island's enduring charm while relishing the convenience of the North Captiva Island Club, granting entry to two pools, a hot tub, kayaks, and bicycles. Seize the opportunity to immerse yourself in the allure of this thoughtfully maintained, petite abode for an unforgettable beach getaway.brStarlink satellite internet gives you high speed access, and two smart tvs can keep you entertained with your favorite streaming services.brGas BBQ grill available.brGetting here involves getting onto a ferry in Pine Island, coming by private boat, or fly in with your own plane. It's worth the extra effort!brBoat slips are available for rent if you are bringing the boat. Are you a pilot landing rights are available with prior authorization from owner. brPlease note, we do not include a golf cart with our home. brGolf cart rental is available from property manager for 80 per day.br

Cottage

Cozy and Private our island home on North Captiva is the perfect escape

Captiva, Florida, United States

Bed

Bath

Sleeps

$327.82

Discover coastal charm and adventure on Captiva Island, with private Gulf beaches and kayaking through Pine Island Sound. Relax in serene cabanas or stroll to Captiva Beach for sunsets. Explore the nearby Captiva Chapel By the Sea. Just a 60-minute drive from Southwest Florida International Airport, this getaway blends relaxation and outdoor fun for an unforgettable experience.brbrThis listing is for a room within a hotel.brbr✦ Your room is 350 sq. ft, equipped with complimentary toiletries, high definition 34-inch TV, available with Netflix, Premium cable, and Standard cable.brbr✦ Cleaning services are available upon request (additional fee may vary)brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open from 6:00AM to 9:00PM, available in the property.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 8:00PM.brbr✦ Free parking lot – 1 space(s).brbr✦ Shuttle service is available upon request for $5.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $250 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $35.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $150.00 (per night). 40 lbs max capacity per pet, max 2 pets/ unit.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Pet fee applies per night, with rates based on weight and room type; an additional cleaning fee may apply in non-approved roomsbr✦ Local shuttle available to island businesses, round-trip with a minimum farebr✦ Beach chairs/umbrella available for daily rent

Hotel

Gulf View Suite w/ Balcony | Pool & Beach Access | Free Parking

Captiva, Florida, United States

1

Bed

1

Bath

Sleeps

$1224.93

Beach House 16 • Captiva Island Vacation RentalbrbrEscape to unparalleled luxury and breathtaking Gulf views at Beach House 16, an extraordinary beachfront retreat. Experience the charm of this meticulously renovated home, where coastal allure seamlessly blends with modern elegance. You'll love the gourmet kitchen, featuring high-end Café appliances and stunning finishes throughout. After a day of exploration, relax in the spacious living area, ideal for family gatherings or cozy nights in. Don't forget to enjoy your private balcony, where you can bask in the refreshing sea breeze and take in the beautiful views. This home is the perfect sanctuary for families or groups seeking an unforgettable island retreat!brbrThis Captiva Island vacation rental is located in the Beach Homes neighborhood of the beautiful resort on the northern tip of Captiva Island. You'll love the great neighborhood amenities like a community pool and BBQ grills. Live on the beach at your next getaway to paradise!br brPlease NotebrSleeps 10brIndividually rented units do not have access to all the resort amenitiesbrSmoking is not permitted

Renovated Captiva Beach House - Beach House 16

Captiva, Florida, United States

Bed