Better search results may be achieved by only checking the amenities that are most important. To view all properties offered, leave the arrival date empty. To see more options, click on view more amenities.

  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  1. Area Information 109 - Manatee Manor

    Directly on the beach in one of North Captiva's most exclusive locations, this architectural delight is truly a great place to play.

    North Captiva at its best. Enjoy Manatee Manor for your next island getaway. Imagine Mexican tile throughout all common areas and Berber carpeting in the bedrooms. Walk out any bedroom to its private patio. Surrounding palms and tropical greenery provide the ultimate in privacy.

    From the 4th level, enjoy breathtaking views of the Gulf of Mexico, Captiva Pass, Cayo Costa Island, and panoramic island views across thick natural vegetation. Spacious, professionally decorated, fully equipped, and professionally managed, Manatee Manor is perfect for a large family retreat or even for four couples seeking a memorable vacation together.

    Manatee Manor is one of North Captiva Island's most popular homes. Advance booking is highly recommended. Read more »
    109 - Manatee Manor
    190 Nighthawk Dr
    North Captiva FL
    26.604546, -82.222301
  2. Area Information 131 - Serendipity

    Serendipity means a "fortuitous happenstance" or "pleasant surprise". It was first coined by Horace Walpole in 1754. In a letter he wrote to a friend Walpole explained an unexpected discovery he had made by reference to a Persian fairy tale, The Three Princes of Serendip. The princes, he told his correspondent, were “always making discoveries, by accidents and sagacity, of things which they were not in quest of”.

    Enjoy one of North Captiva Island’s Best vacation homes offered. Serendipity is a fabulous 4 bedroom home with incredible Gulf of Mexico views!. This amazing home has it all! From the moment you arrive you will be mesmerized by the wonderful appointments, furnishings, amenities and sweeping views of the Gulf of Mexico. The home has 2800 square feet under a/c with more than 4000 square feet of living space including open and screen decks. It was renovated and professionally decorated from top to bottom in February 2014. Most everything in this home is brand new including AC units and the pool heater!

    Serendipity has a private screened pool area just steps to the beach. This home is built for island living and setup for large multi-generational families. North Captiva is an amazing place to explore and Serendipity is equipped with two golf carts to explore the island.

    There is plenty to do at Serendipity with a heated pool, games, beach chairs and towels. Also enjoy cooking in a gourmet kitchen with brand new stainless steel appliances and lots of granite counter space to work. The home has 3 flat screen TVs with Directv and a lovely look out lounge. You won’t want to leave this amazing place. The home allows up to 10 people and there is plenty of room to stretch out with a game area, living room, many porches and a lovely pool area. Also, enjoy a fabulous roof top deck with sunset and sunrise views - this deck has some of the best views on the island with cable railings for unobstructed viewing.

    The sleeping arrangements are top notch with 2 master bedrooms with private baths and access to the outside porches. Let’s not forget about great views. You will truly be pleasantly surprised when arriving at Serendipity.


    1st level:
    Master Bedroom 1:
    King Bed with gel top mattress
    Flat Screen TV
    Access to screened in balcony
    Full Bath with walk in shower – pebble stone shower floor and seamless glass surround

    Master Bedroom 2:
    Queen bed with gel top
    Flat screen TV
    Access to screened in balcony
    Full Bath with shower/bathtub combo

    Bedroom 3:
    Bunk beds – One Full, One twin
    Gorgeous Nautical décor with closet and dresser space

    Bedroom 4:
    Two twin beds
    Storage space under beds and closet

    Full Bathroom:
    Bathtub/Shower combo
    Granite top vanity

    Overall amenities on 1st floor:
    Professional Décor with custom window treatments and new furniture in all rooms
    All New ceramic tile throughout, luxury shower heads, granite tops, sinks, faucets, lighting
    New Mattresses and high end linens and bedding in all rooms
    Quality “Down-Like” Pillows with extras in closets to find your perfect fit
    All mattresses and pillows have soft, quality protective covers
    3 Blowdryers – one in each full Bathroom
    Bath and Hand Towels Provided by Island Club
    10 Beach Towels in foyer storage ottoman supplied by owner
    Laundry baskets and hangers in each closet

    Laundry Closet with Washer and Dryer
    Iron and Ironing Board

    2nd level:
    All new flooring throughout 2nd floor
    Professionally decorated with all new paint and custom window treatments
    Beautiful gulf views from every window on this level
    Living room with 2 large sofas – one with pull-out memory foam full size mattress
    Pub table area with storage chest for games, puzzles, or extra eating area

    Gourmet Kitchen with all new granite, sink, faucet, stainless steel appliances – dishwasher, side-by-side refrigerator with RO filtered ice and water in door, microwave, electric stove. Garbage disposal, wine fridge, 12 cup and 4 cup coffee makers, 4-slice toaster, blender, hand mixer, large electric griddle, pots, pans, skillets, bakeware, cutting boards, new dishes, glasses, silverware, cooking utensils, wine glasses, and outdoor plastic dishes and glasses for eating by the pool

    Reverse Osmosis Drinking Water system at kitchen sink for quality drinking water
    Insta Hot faucet at sink for steaming hot water for tea and other hot drinks instantly

    Dining Table for 10
    Breakfast Bar with new granite and 3 swivel barstools
    Pantry closet for food storage
    Tennis Racquets in pantry for use at NCIC tennis courts

    Half Bathroom with new Granite top and designer bowl sink

    Wireless Access
    Landline Phone
    Large Flat Screen TV with DirecTV
    DVD player
    Assortment of movies and books
    Sound system

    Sliders to outdoor screened in balcony on this level – covered to enjoy in any weather
    Outdoor Dining Table for 6
    Outdoor Sectional seating

    3rd level:
    Spiral Staircase to this cozy loft area – overlooks LR/Kitchen area
    New flooring
    2 extra large chairs with stunning gulf views
    4 New Quality sliders to access outdoor decks with aluminum decking and cable railings

    4th level:
    Large Upper level outdoor deck for sunbathing, gulf and island viewing
    Lounge chair seating and side tables
    Aluminum decking and cable railings
    This level has views of the entire island and spending time here is a must in this house!
    Views of the sunrise over the bay in the morning
    Sunsets over the gulf up here are magical!
    Serendipity is close to the airstrip and you will experience the thrill of occasional small plane take offs and landings as they fly right by

    Pool/Ground Level:
    Large in ground heated pool with screened in area and decking all around
    Patio dining table for 6
    Lounge chairs for sunbathing
    Pool toys and noodles
    Outdoor shower
    Outdoor Pool bar with sink
    Small fridge
    Beach chairs to take for the short walk to the beach

    Weber Gas Grill – new in February 2014

    2 Golf carts available with this home Read more »
    131 - Serendipity
    4611 Seair Ln
    North Captiva FL
    26.6034, -82.22313
  3. Area Information 176 - All Conch'ed Out

    This is a beautiful new home with all the features that makes it the perfect tropical island vacation rental. Nicely decorated with a floor plan that will make you feel right at home. Beautiful hardwood floors and tile is just a start. You have fantastic views from the upstairs deck and it's centrally located making it easy to get to the beach, go to the nature preserve or enjoy the club amenities with a short trip. Read more »
    176 - All Conch'ed Out
    4451 Conch Shell Drive
    North Captiva FL
    26.594579, -82.219981
  4. Area Information 150 - Keylime High

    Gorgeous 3 bedroom home newly decorated, with Gulf view, private pool and a bar making this one of, if not the best home on the Island for entertaining guests.

    Starting at the top floor is a Master bedroom suite with a nice sitting area with tv, a deck with hot tub showing off the breath taking views of the Island and The Gulf Of Mexico. Down to the main floor you'll find a beautifully decorated living room with decks and a TV with VHS/DVD/Direct TV. The dining room seats 6 and the screened porch just off the dining room has seating for 4 with ceiling fans. A very bright and cheery fully equipped kitchen with an ice maker, microwave and island bar. The Queen guest bedroom is nicely decorated, has a deck and shares a bath with the other twin guest bedroom. The twin guest bedroom can easily convert to a king. Below the home on the ground level is a private pool with solar cover, and a fantastic bar for entertaining guests. It features a flat screen tv to watch your favorite sporting events or maybe movie night. It has a commercial ice machine so you won't run out making your favorite frozen drinks. Cook all your favorite tailgate food on the Weber gas grill. Read more »
    150 - Keylime High
    4550 Cutlass Dr
    North Captiva FL
    26.595921, -82.222204
  5. Area Information 163 - Pelican Pointe

    This 4 bedroom home has the best views on the island! Walk out your door onto the beach.

    Pelican point, brand new (Dec 2007) 4 bedroom luxury home only 12 steps to the Gulf of Mexico waters. Only a sugar white sand beach seperate you and the Gulf of Mexico. Enjoy some of the most incredible views of the Gulf, Pine Island sound and Cayo Costa (A state owned park) from Pelican Point.

    This luxury home is set up for an extended family or multiple families. Bring your boat because a nice boat slip is included. Enjoy swimming at the resorts pools or dine in the restaurants or have lunch at the pool bar. Everything you need is right here at Pelican Point. Over 2200 square feet of living space with another 1200 square feet of decks. Read more »
    163 - Pelican Pointe
    120 White Pelican Drive
    North Captiva FL
    26.605999, -82.221424
  6. Area Information 005 - The Crews Nest Property

    Luxury 2700 square foot beach house with private pool and spa just recently refurbished. Comes with 2 golf carts!!!

    Crew's Nest photo gallery (81 photos)

    This stunning multi-level, multi-deck home is located just yards from the pristine North Captiva beaches of the Gulf of Mexico. This island beach rental is designed with comfort and luxury in mind, and with the utmost attention to capturing the beauty of the creation all around.

    Enjoy the Crews Nest, an architectural delight providing a standard of living second to none. This lovely beach view home is brand new and there is no shortage of quality and award winning elegance here. 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 be.

    As you enter into the Crews Nest you will be taken away by the combination of elegance and comfort visualizing the beautiful living room furnishings and decor. Truly a delight. This high standard of living is well complemented with a surround sound entertainment system and wet bar. Leather couches and love seats and Old Florida style paddle fans through out.

    On the upper level is a lovely gourmet kitchen with top of the line appliances. A formal dining room with glass windows from floor to ceiling for dramatic views of the emerald waters of the Gulf of Mexico. A second living room is on the upper floor with another entertainment system.

    The bedrooms are lavishly furnished and equipped. If youre not careful you will mistake yourself for being in a suite at the Woldorf or Ritz. Go up another level into the Sky lounge crews nest and be taken away by the panoramic views of the Gulf of Mexico and Island scenery.

    Bask in the sun by your own private pool and spa or enjoy a dip after shelling on the beaches. This will be truly an unforgettable adventure you partake on. Book now or risk missing the opportunities times still available at the Crews Nest.

    Comes with 2 golf carts!!!

    Read more »
    005 - The Crews Nest Property
    4541 Cutlass Drive
    North Captiva FL
    26.595547, -82.221992
  7. Area Information 159 - Flamingo House

    Flamingo House is a brand new home, completed in winter 2004, with a special island flair. Carved flamingos on the eaves, conch shells, pineapples and palms carved in the railings. Truly a beach house 200 steps from the Gulf beach.

    First floor includes heated outdoor pool withdeck and charcoal Weber grill. Second floor is living area andbedrooms. Open plan kitchen with bar serving 6 and adjacent dining roomfor 8, large living room with entertainment center including satelliteTV, DVD and Karaoke. Lanai covered deck with outside eating overlooksthe pool. The master bedroom includes queen size bed, walk-in closet,private bath with separate Jacuzzi, and walk-in shower. The otherbedrooms have a queen and 2 twins. The living room has a queen sleeper.Also included are a washer and dryer, linens and beach towels.
    Above it all is an observation deck with breathtaking views of the Gulf, Pine Island Sound and North Captiva Nature Preserve. Read more »
    159 - Flamingo House
    4510 Butterfly Shell Drive
    North Captiva FL
    26.593855, -82.221518
  8. Area Information 102 - Eventide Sunsets

    Eventide Sunsets is a great choice for your next family retreat. Located just off the beach, it offers unobstructed views of the Gulf's emerald waters.

    Eventide Sunsets is beautifully decorated with warm colors throughout. A highlight is the rich wood-paneled cathedral ceiling in the living/dining area. The furnishings are high quality and very comfortable. This house provides every amenity imaginable for a comfortable stay.

    Views are breathtaking from Eventide Sunsets, looking out as it does over the Gulf of Mexico and state land preserve. Access to the beach is very convenient, actually less than two minutes' walking distance. This home is well worth booking for your next retreat. Read more »
    102 - Eventide Sunsets
    4560 Panama Shell Drive
    North Captiva Fl
    26.5934199, -82.222829
  9. Area Information 149 - Junonia

    Just renovated and decorated beautiful island home. Walking distance to the beautiful Gulf beach. 3 Bedroom 3 Bath. Read more »
    149 - Junonia
    577 Coral Circle
    N Captiva FL
    26.598228, -82.222098
  10. Area Information 069 - Casa La De Da

    This lovely 5 bedroom upside down home is situated directly on the Gulf of Mexico. Plenty of space for a large family or two families. King Master Bedroom w/Private Bath/Guest Bunk w/Double on bottom & 2nd Bunk bed set /Guest Twin Bedroom all w/Shared Bath. Double Guest w/Private Bath/Laundry Room Decks off of each Bedroom.Outdoor lounging Mermaid Deck Upper Level:Master King Bedroom w/Private Bath/Kitchen/Breakfast Bar/Dining Room/Living Room w/Sleeper Sofa w/Screened rooms. Bathroom/Internet Access/Charcoal Grill/Steps to the Beach. Enjoy your cocktails at the deckside Tiki Bar or find your favorite spot to curl up with a book, to listen to music or to watch a movie from the extensive dvd/video library.

    Casa La De Da , your beach home awaits – from the brilliantly hand painted mural in the foyer to the open, sun-washed great room, the ocean breezes and magnificent sunsets are yours to enjoy as you relax with family and friends. The gourmet kitchen with it’s ocean view is a delight. The spacious dining area seats 10 comfortably under the whimsical monkey chandelier. Enjoy your cocktails at the deckside Tiki Bar or find your favorite spot to curl up with a book, to listen to music or to watch a movie from the extensive dvd/video library. At the end of the day you can retreat to one of the 5 uniquely decorated bedrooms, each with it’s own distinctive charm. Casa La De Da sleeps 10 in comfort. Read more »
    069 - Casa La De Da
    4599 Schooner Drive
    North Captiva Fl
    26.5971943, -82.2227777
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
239-395-1001 | | | 5576-1 Doug Taylor Circle, St. James City, FL 33956