Holiday rentals with a pool in Sanibel Island

4.96 out of 5 average rating, 46 reviews

A scenic view showcases a private deck featuring a spa and circular seating area, positioned near lush greenery. The serene beach is visible in the background, leading to calm waters under a softly lit sky at sunset, creating a tranquil coastal atmosphere.

Home in Captiva

Beachfront North Captiva | Rooftop Deck | Hot Tub

No bridges. No cars. No crowds. Stella Maris sits directly on the Gulf on North Captiva — a private barrier island reachable only by boat. Step off your deck onto white sand. Watch dolphins from your 360° rooftop deck at sunset. 3 bedrooms, each with private en-suite bath. Cathedral ceilings, gourmet kitchen, formal dining with Gulf views, stone fireplace, hot tub, and included golf cart. Dual club access — Safety Harbor Club included; optional Island Club for pools, kayaks, bikes, and pool bar.

A screened lanai is furnished with a small round table and four chairs, providing a cozy dining space. Beach chairs are stored on the wall, with a view of the lush green lawn and distant ocean visible through the expansive glass sliding doors.

4.98 out of 5 average rating, 57 reviews

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.

4.97 out of 5 average rating, 132 reviews

A clear blue pool is surrounded by a spacious patio, featuring comfortable loungers partially immersed in the water. The inviting outdoor space overlooks the serene canal, while the covered lanai offers additional seating options. Lush palm trees sway gently in the background under a bright sky.

Home in Cape Coral

Boater’s Paradise-Stunning Sunsets! Games Room!

Renovated lanai! This 3 bed/4 bath home is on the nicest canal with 200+ ft of frontage & gorgeous views of the canal & sunset. The pool, tiki hut & docks have full sun all day. Each bedroom has a private bath & there's a 2 pc powder room off the laundry. The primary has a king bed & walkout to pool. The 2nd bedroom has a queen bed & pool access. Bedroom 3 has a queen & private bath. Fully equipped kitchen with everything you need. And a games room! Enjoy stunning sunsets under the tiki hut.

4.99 out of 5 average rating, 240 reviews

The screened-in pool area features a serene swimming pool with shimmering water, two blue lounge chairs positioned nearby, and views of a wide canal. A thatched-roof Tiki hut can be seen across the water, surrounded by lush greenery.

Home in Cape Coral

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!

A panoramic view of a sandy beach stretches out towards the horizon under a clear blue sky, dotted with white clouds. Beach chairs are set up along the shore, with lush green vegetation in the foreground, leading to the water's edge.

4.95 out of 5 average rating, 105 reviews

100+ 5 Star Reviews and Right on The Beach!

We are a Superhost for a good reason! 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. 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.

An open concept living area features a modern sectional sofa, complemented by a patterned area rug and decorative pillows. Natural light filters through large windows, illuminating the adjacent kitchen with wood cabinetry. A dining table is set, inviting gatherings in a spacious environment.

4.96 out of 5 average rating, 25 reviews

Sanibel Vibes - Relax, Unwind, and Enjoy!

Welcome to this beautifully designed open-concept residence located on a serene and exclusive neighbourhood. This spacious home with high ceilings and abundant natural light features 5 bedrooms and 4 full bathrooms, along with a large living room and a separate suite for a perfect blend of privacy, comfort, space, and style. The large backyard with a heated pool for year-around swimming backs onto a beautifully maintained golf course with scenic lakes, offering breathtaking views and sunsets.

5 out of 5 average rating, 17 reviews

Steps to the beach Bikes & Beach Gear Weekly Stays

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 | 🚲 4 Bikes included | CoolCabanas tent

Superhost

4.6 out of 5 average rating, 5 reviews

Sanibel Beachfront Condo | Shelling Paradise

Beachfront 2BR/2BA condo on beautiful Sanibel Island, famous for world-class shelling and sunsets. Enjoy Gulf views from the living room and master bedroom. Includes a fully equipped kitchen, open living area with sleeper sofa. Full size washer and dryer are in the unit. The Pool and tennis court are currently under construction Free parking and direct beach access. Perfect for families, couples, or friends looking to relax, explore, and experience the natural beauty of Sanibel Island.

The exterior of the retreat features a welcoming porch adorned with a green bench. Lush tropical foliage and palm trees surround the property, enhancing the coastal charm. A gravel pathway leads to the entrance, offering a warm approach to relaxation.

4.96 out of 5 average rating, 25 reviews

Mangoes (Left Side)

Discover an escape to Mangoes, our Sanibel retreat where luxury and coastal charm intertwine. This haven features a full kitchen, living room, master bedroom with its own bathroom, bluetooth speakers, guest bedroom, and one pull-out couch. We've got you covered with starters — coffee, tea, etc. Step outside to discover an oasis with a HEATED SALTWATER POOL, hot tub, and grill. Just a short walk to the beach, Mangoes captures the essence of Florida living—sun, sand, and sea!

Superhost

Apartment in Sanibel

5 out of 5 average rating, 3 reviews

Sea La Vie

Nestled in the exclusive Kings Crown condominium complex on the quiet west end of the island, this luxurious 2-bedroom, 2-bathroom newly remodeled condo offers direct beachfront access and breathtaking gulf views. It's perfect for creating unforgettable family memories! Step out of the door to miles of pristine shoreline, renowned for world-class shelling and gentle waves ideal for kids. * The pool is expected to be open after inspection in the spring of 2026

A heated saltwater pool is enclosed by a spacious screened area, allowing for relaxation and sun exposure. Lounge chairs and vibrant orange seating are positioned beside the water, with views of a tennis court visible through the mesh walls and lush landscaping beyond.

4.98 out of 5 average rating, 60 reviews

Coastal Chic Island Escape

Just 150 yards from Sanibel's peaceful beach, our home offers unmatched luxury: direct beach access, a heated saltwater pool, private pickleball/tennis court, and sea-view dining. A king suite, additional king bedroom, playful bunk room, and separate apartment provide comfort for all. Perfect for those seeking a serene escape, our home is not suited for loud gatherings or parties. Please help us preserve the tranquility of this special place. 28-day minimum.

Superhost