
Holiday rentals with a pool in San Carlos Island
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Top-rated rentals with a pool in San Carlos Island
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

McGregor’s Gem• Heated Pool 3BR/2BA River District
🌴 Welcome to McGregor’s Gem—your ideal Southwest Florida retreat! Dive into relaxation in your private heated pool, spread out across three bedrooms and two baths, and enjoy the perfect blend of peaceful tree-lined neighborhood living just minutes from the charming Downtown Fort Myers River District, world-class beaches, and top local attractions.☀️ Whether you’re traveling with family, friends, or on business, this home offers all the modern comforts you need for a relaxing, stress-free stay

Ft. Myers Quaint Getaway! Minutes from Beach!
My condo is close to the beach, NOT on the beach, nightlife, public transport, and family-friendly activities. It is good for couples, solo adventurers, business travelers, and families (with kids). It's minutes from Ft. Myers and Sanibel Beach. It has a King size bed in the master bedroom and two twin murphy beds in the guest room. Walking distance from a Super Target. Several outlet malls, closest is 2 miles. FYI, not handicap accessible (second floor unit). A few steps to the pool and grill.

Island Oasis Steps From the Sugar Sand Beach
Important Note: This apartment had no damage from hurricanes in 2024. Everything is perfect here. Beaches are beautiful, pool is relaxing and welcoming. Thankfully the island restaurants and bars are also back up and going in fun island style! Beaches are beautiful and our brand new pool is complete and ready to enjoy. Be one of the first to enjoy this complete remodel renovation. No expense was spared here. Top quality memory foam mattresses with high end bed linens for a restful sleep. F

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.

Beachfront, Water Views Estero Beach Tennis 708A
Wake up to stunning sunrises and wind down with breathtaking sunsets in this beautifully renovated beachfront condo on the South End of Ft Myers Beach. Enjoy luxury finishes throughout, including a sleek quartz countertop kitchen, modern appliances, and a spa-inspired walk-in shower. The layout and private balcony offer unbeatable ocean & bay views, making it the perfect escape for relaxation, comfort, and coastal elegance—all just steps from the sand. 708A is where your dream vacation starts!

AquaLux Smart Home
Unwind in style in this spacious and modern home. Here's what awaits you: Smart Home Technology: Control lights, temperature, and even the front door with voice commands or your smartphone for a seamless experience. Heated Saltwater Pool: Take a refreshing dip in the sparkling pool, perfect for year-round enjoyment. Dedicated Workout Area: Maintain your fitness routine with a private space equipped for exercise. Freshwater Canal Views: Wake up to calming water views and the sounds of nature.

5 O’Clock at Miramar
It’s always five o’ clock at our cozy oasis located just steps from Fort Myers Beach! Quaint street close to Times Square & Margaritaville. Short 2-3 min walk to deeded walkway to Fort Myers Beach. Boating your thing? Canal access at the end of the street. Ranch home (no steps!) that sleeps up to six with two king bedrooms, one Murphy queen bed, pull-out couch, two full baths, stocked kitchen, wifi, laundry, ample parking! Pool with sundeck. Kick back & relax your cares away! FMB STR# 22-0240

Salt Life-beautiful 2 bed/1 bath-pool-hot tub-tiki
This charming two-bedroom, one-bathroom home is perfect for families, offering comfortable beds and a relaxing atmosphere. Just under half a mile to the beach, Margaritaville, and great restaurants, it’s ideally located for both fun and convenience. Outside, enjoy a private oasis with a saltwater pool, hot tub, and a patio featuring a grilling area and dining space. The large tiki hut offers a lounge area with a smart TV. Located on a canal, it’s perfect for kayaking or fishing off the dock.

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🏖️

Walk to Times Square, steps to the Beach!
Welcome to your perfect beach getaway! This bright and inviting 2-bedroom, 2-bath vacation rental is ideally located just across the street from the sandy shores of Fort Myers Beach, with easy beach access just a short walk away. You'll also be just a quick stroll from vibrant Times Square—home to great restaurants, shops, live music, and fun nightlife. This comfortable and well-appointed home offers everything you need for a relaxing stay! Come experience the best of Fort Myers Beach!

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.

Villa Sorrento · 2025 Luxury · Walk to Town-Beach
Location, location, location! Personally hosted by Paul & Alicia of Dancing Palms Vacations, this stylish coastal home offers a brand-new experience with a spacious lanai and fenced pool backyard—just a short walk to the white sugar sand beach and town with restaurants, bars, and shops. Start your day with coffee on the covered porch and Gulf or bay peeks. Lounge by the heated pool, grill out, or unwind in cozy outdoor seating. End your day with a sunset stroll or walk to town.
Popular amenities for San Carlos Island rentals with a pool
House rentals with a pool

Luxury Beachside House W/ Heated Pool & Elevator

Paradise Palms A Desirable Pool Home-Fall Special

Aqua Vista - Luxury Vacation Rental Cape

Pool, Mini Golf & Arcade Family Fun Retreat!

Heated Pool, Hut Tub, Dock, Bikes, Beach Gear!

Modern New-Build Luxury Villa!

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

Canal-front Paradise Retreat
Apartment rentals with a pool

**Luxury Beach Front Condo w/ Pool in heart of FMB

Beachfront @ Elevate in the Sun!

Rare walkout condo on Sanibel beach-Fully Restored

Beachfront fully equipped apartment

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

November special

Oceanview unit. Completely remodeled Pool is open!

Bonita Beach and Tennis 3907 - Ocean Views
Other holiday rentals with a pool

Family Oasis | Heated Pool + Beach Gear, Kid Ready

Canal View! Walking distance to Marina Village

2BR Vacation Condo Near Ft Myers Beach & Sanibel

Cape Escape | Hot Tub | Heated Pool | Game Room

Seaside 204 Beachfront condo - Luna Sea on FMB

FMB -ESCAPE, Heated Pool on Canal

View of Gulf, Steps to Beach@The Turquoise Turtle

Sundial E304: Gulf Front Sanibel Island Paradise
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