Waterfront holiday rentals in San Carlos Island

Lanai Pool Home w/ Spillover Spa Near Beaches

Welcome to Sunseeker, your private Florida escape designed for relaxation, sunshine, and unforgettable moments. This spacious home offers the perfect blend of comfort and coastal charm, featuring a heated saltwater pool and spillover spa inside a fully enclosed lanai—ideal for enjoying warm days, sunset cocktails, and peaceful evenings by the water. Whether you're lounging poolside, grilling on the patio, or watching local wildlife like herons and otters pass by, every moment here feels like a getaway. Inside, you’ll find inviting living spaces designed for both connection and comfort. With multiple living areas, a fully equipped kitchen, and a dedicated office space, Sunseeker is perfect for families, groups, or remote work stays. The home comfortably accommodates up to 8 guests, making it a great choice for beach vacations, winter escapes, or extended stays. One of the home’s unique touches is its seasonal fruit trees, where you may enjoy fresh oranges or mangos right from the yard—adding a true taste of Florida to your stay. Conveniently located near top Southwest Florida attractions, you’re just minutes from beaches, dining, and entertainment while still enjoying a peaceful, private setting. Quick Highlights: - Heated saltwater pool with spillover spa - Fully enclosed lanai for year-round enjoyment - Spacious home with multiple living areas - Sleeps up to 8 guests comfortably - Fully equipped kitchen for home-cooked meals - Private den/office for remote work - Outdoor grill and patio seating - Peaceful water views with local wildlife sightings - Seasonal fruit trees (oranges & mangos) - Quiet neighborhood on over half an acre - Close to beaches, dining, and local attractions Sunseeker is perfectly situated for exploring the best of the area, including nearby beaches, island getaways, and vibrant downtown experiences. Whether you're here for sun-soaked beach days, boating adventures, or relaxing poolside, this home offers the ideal home base. Things to Know: - Maximum parking for 2 vehicles - Beach gear and baby items are not guaranteed but may be available upon arrival - Furniture and décor may vary slightly from listing photos - The property is located in an area that may have ongoing construction due to recent hurricane recovery efforts - Possible impacts include noise, nearby projects, or increased traffic - Construction conditions are outside of host control and not eligible for refunds or compensation If you're looking for a relaxing Florida vacation rental with a private pool, great location, and plenty of space to unwind, Sunseeker is ready to welcome you.

Beach · View · Sleep quality

Drift House · 6 King Suites · Boat Dock

Hosted by 5-star hosts Paul & Alicia of Dancing Palms Vacations, Drift House is a newly built home just under a five-minute walk to the beach, a short walk to Times Square. The main living area opens to a covered porch overlooking the pool/canal below, opening the home through a wall of glass to the outdoor space. With six king bedrooms, each with a private bath, plus a heated saltwater pool and spa. Drift House gives groups the rare luxury of staying together without giving up space or privacy.

Beach · Hot tub · Location

100+ 5 Star Reviews and Right on The Beach!

We are a Superhost for a reason! Sanibel Siesta looks amazing! Immaculate beachfront, 2BR, 2BA w/garage, nicely updated beachy unit at sand's edge. Cooks kitchen. Amazing views of the Gulf w/5 star ratings! 3-day min. New hurricane windows, nicely furnished with ELEVATOR IN BUILDING! Discount for weekly/mo. rentals. BR 1:King bed ensuite, smart TV. BR 2: 2 tw. beds, smart TV. Qn. sofa bed in LR. Pool, golf course, bikes, laundry on site. No food or condiments stored in unit. May allow sm. dog.

View · Beach · Laundry

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

Beach · View · Decor

Luxury Riverfront Retreat • Pool & Spa • 60ft Dock

Luxurious 4BR 3.5Bath villa located in a prime location, directly on the Calosahachee River in a sought-after waterfront area near downtown. Magnificent expansive backyard with high-end amenities and direct river access ✔ 4 bedrooms ✔ Open Design Living ✔ Full Kitchen ✔ Patio (Pool and Hot tub, Bar, Dining, BBQ) ✔ Expansive Tropical Yard ✔ Indoor/Outdoor Surround Sound ✔ 7 Smart TVs ✔ High-Speed Wi-Fi ✔ Large Private pier/dock w/ boat & jet ski lift and a Tiki Hut! See more below!

River · Beach · Amenities

Paradise on canal minutes to Ft Myers Beach/Gulf

Beautiful 3 Bedroom, 3 bath home on a canal with a dock! Bring your boat or jet skis! Enjoy a relaxing stay watching the dolphins and manatee right off the dock. This exquisitely updated home has everything you need for a fantastic vacation. Especially location! 5 minutes to Ft Meyers Beach. Enjoy the resort right in your own backyard. New pool with hot tub and sun shelf. Enjoy beautiful sunsets off the huge patio. Trolly to beach at neighborhood entrance or walk to in minutes.

View · Beach · Check-in

Sundial E304: Gulf Front 3BR w/Stunning Ocean View

BRAND NEW - RIGHT ON THE BEACH! Enjoy stunning direct gulf-front views from nearly every room at this relaxing 3BR coastal retreat. This luxury residence was fully renovated to include a custom expanded kitchen, 2 gorgeous bathrooms, and washer & dryer. Top of the line coastal furnishings in every room. The large master bedroom offers spectacular gulf views & a full-size desk in case you need a quiet space to work. WiFi has been fully upgraded to make streaming and video a breeze.

View · Beach · Nearby

Cap't Jack's Waterfront Cottage

Escape to Captain Jack’s Cottage, a newly renovated canal-front retreat perfect for up to 4 guests. Just a 10-15 minute walk to the sandy beach, this charming home offers a tranquil vibe with modern amenities, a private patio, and stunning water views. Walk to local restaurants or hop on the nearby beach trolley. Whether relaxing or seeking adventure, Captain Jack’s Cottage is ideal for a memorable coastal getaway. Book now and unwind in paradise!

Beach · View · Quiet

Dolphin beach house 2

ONE OF THE BEST WATERFRONTS IN CAPE CORAL! A short walk to the beach . This 2,500+sq ft home has stunning sunsets and South Western water views from all main living areas,as well as the Master Suite. Heated pool w/ LED colored lighting, built in Spa,Pool bath, full laundry facility, Lanai,Fireplace ,Wi-fi and TVs in every bedroom, private dock . Boat on lift for rent w/RPM rentals . Large 2-car garage w/5 bicycles,beach wagon & cooler on site.

River · Beach · Bathroom

Icon on the bay - Panoramic views/Rooftop hot tub

Waterfront fun meets luxury in this 3-story Fort Myers Beach home on San Carlos Island! Featuring 4 bedrooms, bay-view living room with balcony, and a full kitchen & dining on the 2nd floor. Enjoy an outdoor kitchen with grill and bar, plus pool table, ping pong & air hockey. Private dock with boat lift and a rooftop deck with turf, lounge chairs & a 6-person hot tub for sunset soaking. Perfect for families, boaters & group getaways.

View · Beach · Access

Primo Paradise

LOCATION is everything! Your family will enjoy easy access to everything from this centrally located property. Walkable to Time Square, the beach, and so much more! Brand new Margaritaville is .2/mile walk. Lani Kai is .3/mile. While at the property you will become obsessed with the pool, canal view, and lanais! This home offers it all! Primo Paradise is also big enough to bring the whole family!

View · Beach · Amenities

Water Front | Modern Open Concept | Beach Vibes

Deck overlooking a mangrove bay, private dock, abundant wildlife & sea life — this is real Florida. Fish off the dock, watch the birds, or just relax in your own space. Skip the stuffy hotel. Walk to Ft. Myers Beach or hop the golf cart shuttle. Bars & restaurants right on San Carlos Island. Key West Express day trip next door. Nature, beach & nightlife — all from your dock.

View · Beach · Decor