Holiday rentals with a pool in Sanibel

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, 98 reviews

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.

5 out of 5 average rating, 32 reviews

An open-plan dining and kitchen area features a mix of stylish seating options. A large table sits in the center, surrounded by chairs, with views of the pool area through sliding glass doors. Natural light floods the space, enhanced by modern ceiling fans.

Home in Captiva

Lookout Escape: Heated Pool, Golf Cart, Outdoor Ba

💰No nickel & diming —AirBnb & cleaning fees in nightly rate! 🌅 360° Gulf-to-Bay Views 🎉 Outdoor Paradise: Pool, Bar, Dart Boards, TVs, Games, Outdoor Shower 🏖️Steps from the Beach! 🍳 Gourmet Kitchen:KitchenAid Appliances & Williams Sonoma Gear 🛥️ Shared boat dock-ask about availability. 🛌 Westin Heavenly Mattresses 🏖 Top-Tier Beach Gear:Chairs, Umbrellas, Cooler & Wagon 🐕 Pets Welcome 🧴 Luxe Amenities: Fine Toiletries & Essentials 🌐 Fast Starlink Internet 😊 24/7 Local Host Support!

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, 52 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.

A private lanai is visible, featuring a small table with two chairs positioned for ocean views. The scene includes lush greenery, multiple palm trees, and the Gulf of America beyond. The nearby resort buildings add to the tranquil ambiance of the outdoor space.

4.97 out of 5 average rating, 30 reviews

Serene Ocean View Escape at Sundial Resort

Private lanai with stunning ocean views — perfect for morning coffee or unwinding in the evening as the sky softens at sunset. Located on the 3rd floor with elevator access, combining great views with easy convenience. Spacious king bedroom with a premium mattress and plush linens for restful nights. Fully equipped kitchen and dining area for evenings in, or take advantage of Sundial’s on-site restaurants just steps away. Resort amenities include restaurants, pool, and a convenience store.

4.95 out of 5 average rating, 44 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

North Captiva Beachfront | 360° Views | Hot Tub

Stella Maris is a beachfront family retreat on North Captiva Island with rare dual club access—Safety Harbor Club included (pool, tennis), plus optional Island Club for pools and kayaks. Enjoy private beach access, panoramic Gulf views, and a 360° rooftop deck for sunrises, sunsets, and stargazing. Cathedral ceilings, gourmet kitchen, and formal dining with sunset views. All three bedrooms feature private en-suite baths. Relax in the hot tub and explore the island with your included golf cart.

4.95 out of 5 average rating, 138 reviews

A serene beach scene showcases smooth, soft sands meeting the gentle waves of a turquoise ocean. A piece of driftwood rests in the foreground, complementing the clear blue sky and tranquil waters that stretch into the horizon.

Home in Captiva

Steps to Beach Captiva Includes CLUB & Golfcart

HOST PAYS AIRBNB FEE WINTER SPECIALS Golf Cart and Club amenities Included North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach STAY WITH US

A bright living area features a light gray sofa and a pale blue accent chair beside a neutral coffee table. A blue and white patterned rug adorns the floor, while a dining area with white bar stools is visible in the background, complemented by a well-equipped kitchen.

5 out of 5 average rating, 12 reviews

Sanibel Condo Steps To Beach - Sandalfoot 4B2

Welcome to Unit 4B2 at Sandalfoot Beachfront Condominium—a serene third-floor retreat offering panoramic views of Sanibel Island’s untouched coastline. This beautifully updated 1-bedroom, 1-bath condo combines modern comfort with coastal charm and places you just steps from the beach, inviting you to experience Sanibel’s breathtaking natural beauty up close. Located on East Beach near the Sanibel Lighthouse. For those seeking beachside tranquility, Unit 2B on the second floor of Sandalfoot

The living area is bright and spacious, featuring light wood flooring and a large flat-screen TV mounted on the wall. Comfortable seating is arranged around a round glass coffee table. Windows allow natural light to fill the space, enhancing the open atmosphere.

5 out of 5 average rating, 8 reviews

Sublime Beachfront Residence at Loggerhead Cay

Loggerhead 253 is a fantastic 2/2 condo residence in the sought after Loggerhead Cay development of Sanibel's East End. As a Gulf-front community located just a matter of feet from the beach, Loggerhead Cay is a favorite among frequent travelers of Sanibel Island. With resort grade amenities including tennis, Olympic sized swimming pool, shuffleboard, and community grills, and a fantastic location with easy on/off island access, Loggerhead Cay is an excellent choice for your next vacation!

4.83 out of 5 average rating, 117 reviews

The modern kitchen features stainless steel appliances, including a stove and microwave. Adjacent, a stacked washer and dryer are positioned beside a minimalist dining area. Natural light floods the space through a nearby window, highlighting the clean lines and neutral color palette.

Condo in Fort Myers

Cozy Coastal Escape. Close to FMB and Sanibel

Looking for a cozy getaway near the ocean? This charming 2-bedroom rental is just a short drive away from the beach! With bright, airy spaces and a modern, open layout, it’s perfect for small families, couples, or anyone looking for a peaceful retreat. Features: • 2 bedrooms • Fully equipped kitchen • Private patio for outdoor relaxation • Private Pool • Minutes from shops, restaurants, golf courses & beaches☀️ Located very close to Fort Myers Beach & Sanibel Island🏖️

5 out of 5 average rating, 12 reviews

Steps to beach + Bikes & Beach Gear Weekly Stays

Take it easy at this unique and tranquil getaway.Relax and unwind at Loggerhead Cay 302 — a bright, beachy end-unit in one of Sanibel’s most sought-after communities. Just steps from the sand, this spacious condo offers coastal charm, a fully equipped kitchen, and all the comforts of home. Enjoy access to a large heated pool, tennis & pickleball courts, beach gear, grills, 2 complimentary bikes and more. Hosted by a 5-star Superhost who’s here to make your stay seamless and memorable.

4.92 out of 5 average rating, 106 reviews

A resort-style pool area is showcased with a stone patio, featuring several lounge chairs and two shaded umbrellas. Palm trees stand nearby, and a rock formation is visible within the pool's edge, complementing the serene outdoor setting.

Home in Fort Myers

Experience of a lifetime

Get ready for the experience of a lifetime at this hidden gem! As you walk through the front door you will begin your journey into the best vacation of a lifetime. Keep on going through the sliders & that will lead you to the incredible resort style pool that will leave you in awe!!! Here you are in the heart of it all. Shopping-dining-entertainment is all within a 5 minute drive. The beautiful beaches just 7 miles away. If you enjoy boating & relaxing this is the place for you.

4.94 out of 5 average rating, 16 reviews

A scenic balcony view showcases a sunset over the water, framed by wooden railings. Two wooden chairs are positioned on the tiled floor, inviting relaxation while overlooking the vibrant sky filled with oranges and purples, creating a tranquil outdoor setting.

Apartment in Fort Myers

Amazing View of Sanibel Harbour

This charming 2nd-floor condo in Sanibel Harbour offers a relaxing retreat with easy parking and elevator access. Enjoy a private beach, swimming pool, and hot tub just steps from your door. Explore nearby attractions like Sanibel Island Lighthouse, J.N. “Ding” Darling Wildlife Refuge, and kayak tours. Located near the Sanibel Causeway with shops and dining, it’s the perfect base for your Sanibel getaway. Book today and start making memories!

Popular amenities for Sanibel rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A sparkling pool is surrounded by a spacious deck featuring lounge chairs and a shaded seating area with an umbrella. The clear blue sky complements the tranquil setting, while a fence provides privacy for guests enjoying the outdoor space.

4.89 out of 5 average rating, 275 reviews

Modern Oasis pool paradise

5 out of 5 average rating, 9 reviews

Aerial view of a spacious waterfront home surrounded by lush greenery. The property features a heated pool with a spa and a tiki hut, offering an outdoor kitchen area. The home's modern architecture and large windows provide ample natural light, while the nearby dock ensures easy access to the water.

Home in Saint James City

Casa Baybreeze - Luxury on Water

An aerial view of a single-story home surrounded by lush green grass and palm trees. The exterior features a warm-colored roof, colorful landscaping, and a pathway leading to the entrance. An American flag is prominently displayed in the front yard.

4.96 out of 5 average rating, 110 reviews

***Relaxation Awaits*** Heated Saltwater Pool Home

4.95 out of 5 average rating, 136 reviews

A living area features a comfortable grey sofa adorned with decorative pillows, complemented by a dark accent chair. A modern coffee table sits centrally, with light streaming in from a nearby window. The space is enhanced by elegant artwork and fans overhead.

Home in Naples Park

Lovely Beach Bungalow pool/spa 1.5 mile bch Naples

A refreshing heated saltwater swimming pool is surrounded by a screened enclosure, featuring two sun loungers partially submerged in water. An oversized teal umbrella provides shade, while a small floating tray holds drinks. The serene canal views are visible in the background.

4.97 out of 5 average rating, 148 reviews

Heated Pool & Game Room Waterfront Family Retreat

The exterior of the house is featured, showcasing a well-maintained lawn and neatly trimmed landscaping. The driveway leads to the front door, flanked by palm trees and colorful shrubs. The home has a light-colored facade with a tiled roof, offering an inviting presence.

4.98 out of 5 average rating, 258 reviews

Gulf access waterfront heated pool

4.94 out of 5 average rating, 124 reviews

A private pool area is framed by vibrant greenery and stone pathways. Lounge chairs are positioned beside the pool, while a shaded seating area with a large umbrella provides comfort. The clean, modern design of the house complements the inviting outdoor space.

Home in Fort Myers

3BR Home w/ Pool near downtown Fort Myers & Edison

The living room features a spacious sectional sofa, providing ample seating. Large glass doors open to the outdoor area, enhancing natural light. A mounted TV displays beach scenery, while a modern fireplace adds a touch of warmth. The room's design promotes comfort and relaxation for guests.

4.98 out of 5 average rating, 121 reviews

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

Condo rentals with a pool

Condo in Fort Myers Beach

The open living area features a comfortable gray sofa adorned with decorative pillows. A wooden coffee table sits in the center, surrounded by a vibrant area rug. The dining area includes a round table with four chairs, and a well-equipped kitchen is visible in the background.

5 out of 5 average rating, 15 reviews

Beachfront @ Elevate in the Sun!

4.94 out of 5 average rating, 108 reviews

The living area features a spacious light-colored sofa accompanied by a rustic coffee table. Large sliding glass doors allow natural light and views of palm trees outside. A flat-screen TV is positioned against a light-coloured cabinet, while a dining table for two is visible on the lanai.

Condo in Captiva

South Seas Resort Beach Villa 🌴 On The Beach !

4.98 out of 5 average rating, 51 reviews

A spacious living area is defined by a soft area rug and wooden flooring. Furniture includes a light blue couch, white dining chairs, and a dining table set. Natural light filters through large sliding doors leading to a balcony, with decorative artwork enhancing the walls.

Condo in Fort Myers

Cathy Condo

4.91 out of 5 average rating, 57 reviews

A marina view is presented through a screened lanai, with several boats docked along the tranquil waters. Lush greenery and palm trees frame the scene, complemented by a pastel sky reflecting the warm hues of sunset.

Condo in Captiva

Captiva Sweet Retreat at Bayside Villas

Superhost

A recently renovated open-concept kitchen and living area feature light wood flooring and modern finishes. A large kitchen island with a blue base provides seating and ample workspace. Natural light enters through the sliding glass doors, highlighting a comfortable seating arrangement adjacent to the kitchen.

Condo in Captiva

4.89 out of 5 average rating, 27 reviews

Waterfront - Bayside Villas Captiva

4.99 out of 5 average rating, 147 reviews

An open kitchen and dining area features a round glass table surrounded by rattan chairs adorned with tropical patterns. Stainless steel appliances are positioned next to light cabinetry. Expansive windows invite natural light, providing a view of the outdoor scenery.

Condo in Bonita Springs

Casa Bonita - Relax @ The Beach (Newly Remodeled)

5 out of 5 average rating, 43 reviews

A screened lanai features comfortable wicker seating with light blue cushions and a central table, offering an inviting space for relaxation. Large windows showcase breathtaking views of the scenic surroundings, while a ceiling fan adds a cooling touch to the atmosphere.

Condo in Cape Coral

Stunning Views Penthouse-Waterview King Suite Golf

An aerial view displays the Breakers West community, showcasing lush landscaping and the inviting swimming pool. The Gulf of Mexico glimmers nearby, with the beach visible in the background. The property sits amidst palm trees, enhancing the natural setting.

4.82 out of 5 average rating, 90 reviews

Breakers West B1, Steps to the Beach!

Other holiday rentals with a pool

A wide expanse of sandy beach stretches under a clear blue sky, with gentle waves lapping at the shoreline. Seagulls are seen in flight and on the sand, while distant beachgoers enjoy the sun. The scene reflects a calm and inviting coastal atmosphere.

4.83 out of 5 average rating, 18 reviews

Beachfront Condo, 2bd/2bath Pet-Friendly

Aerial view of the coastal area showcasing Cyprina Beach #10 among nearby buildings. The turquoise waters of the sea can be seen in the background, with sandy beach in the foreground. Lush greenery surrounds the properties, highlighting the proximity to nature.

4.75 out of 5 average rating, 8 reviews

Sanibel Condo - Steps To Gulf - Cyprina Beach #10

5 out of 5 average rating, 17 reviews

A studio living space is displayed, featuring a kitchenette with modern appliances, including a full-sized refrigerator. A small dining table with blue placemats complements the area. Twin bunk beds are positioned against the wall, with cozy bedding visible. Natural light filters in through the windows.

Guest suite in Sanibel

Sanibel on the Canal

5 out of 5 average rating, 7 reviews

A spacious living area features a vibrant area rug beneath two upholstered chairs with floral patterns. Natural light filters through large windows, illuminating the room. An arched entrance leads to a dining area set with a wooden table and chairs, further enhancing the open layout.

Home in Sanibel

Gulf House with pool

Home in Sanibel

5 out of 5 average rating, 3 reviews

Seabreeze Sanctuary

The screened lanai features blue adirondack chairs and a small table, offering a view of the sandy beach and gentle waves. Green foliage is visible below the lanai, with the expansive Gulf of Mexico stretching out in the background under a clear blue sky.

4.85 out of 5 average rating, 13 reviews

Sundial A306

5 out of 5 average rating, 22 reviews

The exterior of a newly remodeled home is shown, featuring a welcoming entrance with a railing and stairs leading up to the door. Lush palm trees and vibrant flower planters are positioned by the entrance, set against a clear blue sky.

Home in Fort Myers Beach

Beach Cottage