Holiday rentals with a pool in Sanibel Island

Right on the Beach with the Best Views and Rates!

Sanibel Siesta looks amazing! Immaculate beachfront, 2BR, 2BA w/garage, nicely updated beachy unit at sand's edge. Amazing views of the Gulf with 5 star ratings! 3-day min. Sustained min. damage from Hurricane Ian. New hurricane windows, freshly painted with ELEVATOR IN BUILDING! Discount for weekly/mo. rentals. BR 1: King bed, en suite, smart TV. BR 2: 2 twin beds, smart TV. Qn. sofa bed in LR. Pool, golf course, bikes, laundry on site. No food or condiments stored in unit. May allow small dog.

Sundial G406 - Brand New w/Beautiful Beach Views

On the beach with top floor ocean views! Enjoy sparkling ocean views from this relaxing coastal retreat, just steps from the beach. This large condo sleeps 4 and was fully renovated to include an expanded custom kitchen & luxury bathroom with large walk-in shower. Top of the line coastal furnishings in every room. The spacious master bedroom offers gulf views, king bed and a full-size desk if you need a quiet space to work. WiFi has been fully upgraded to make streaming and video a breeze.

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!

Welcome to Paradise at CollinsCoveCaptiva!

Welcome to your dream getaway in this beautifully updated, turnkey Key West-style home located in the heart of Captiva Island within walking distance to the village. Nestled in the charming Sunset Captiva community—lined with brick-paver streets—this home offers direct access to award-winning beaches and a private marina on the Bay. Boater’s Paradise? Immediate availability for the brand-new HOA-maintained boat docks. Or spend your days relaxing in the oversized, heated resort-style pool.

Gulf House with pool and generator.

Beautiful single family house with an elevator and backup generator right across the beach. Large kitchen with morning nook and dinning area overlooks the beach. Tastefully decorated with designer furniture. Private backyard, backs to nature reserve. Covered all season pool with shower, gas grill and outdoor dining table. Beautiful landscaping! Close proximity to restaurants and all amenities. Enjoy with beautiful sunsets from front yard or take a stroll on the beach across the street.

Premier Beachfront Residence at Villa Sanibel

Don't miss out on the opportunity to experience this beachfront condo in the exclusive Villa Sanibel development. Featuring a walkout patio facing the beach, you can quite literally roll out of bed onto the beach. Featuring two large bedrooms, two upgraded bathrooms, a well appointed kitchen, a spacious patio, access to fantastic amenities and your very own private beach access, this unit is a beachgoer's dream. Fully renovated in 2025 and available for the first time since hurricane Ian!

Blue Laguna - Vacation in paradise!

Beautiful and welcoming are just two words to describe this magnificent, 4 story home with heated private pool and sweeping 360 degree water views from the observation deck. Blue Laguna features 3 bedrooms and 3 full baths allowing this home to sleep up to 6 people. Two screened in lanai's so you can sit and enjoy the island breeze and leave the sliding doors open for a true island nature experience during the colder seasons. A golf cart for 4 persons is also included in the rental.

Loggerhead Cay 332 + Bikes + Paddleboard

Loggerhead Cay #332 is your perfect Sanibel escape — just steps from the beach, beautifully decorated, and packed with thoughtful touches. After a day of shelling, biking, or lounging by the oversized pool, come home to a spacious, serene retreat. Whether you’re exploring the nearby Lighthouse, enjoying breakfast at Lighthouse Café, or grabbing essentials from Jerry’s, everything you need is right here. ✨ Beachfront location | ☀ Oversized heated pool | 🚲 Bikes included

Waterfront 2BR Condo (Fully Updated!) w/ 2 Bikes!

This unit has been updated, including an extended kitchen, granite counter tops, impact windows and doors, ceramic tile and a full bath along with a second half bath. This corner unit allows for outstanding canal views and privacy. Tennis and heated pool are just downstairs. Two bicycles are available. Please note that small construction projects are still taking place on the grounds outside due to Hurricane Ian. Enjoy!