Pet-friendly holiday rentals in Sanibel

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

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.

Blue Laguna - Vacation in paradise!

This bright, fully equipped welcoming three‑story home features a private heated pool and a rooftop observation deck with stunning 360‑degree water views. It offers three comfortable bedrooms and three full bathrooms for up to six guests, plus two screened lanais where you can relax in the island breeze and listen to the birds. A four‑seater golf cart is included, so you can easily explore the beaches and sandy paths of beautiful North Captiva Island. Also full access to Island Club amenities!

Island Paradise-The Sandy Banana-across from beach

Relax and enjoy a little taste of paradise in this beautiful home with 3 master suites and a large loft area that has twin beds that double as a sofa, its own coffee bar and mini fridge. Tucked in and surrounded by beautiful sea grapes and palm trees you'll feel like its your own private oasis. Located on the quiet west end of Sanibel Island only a two minute stroll to one of the quietest beaches on the island. You're sure to enjoy nightly sunsets over the Gulf of Mexico during your stay!

Steps to Beach Captiva Includes CLUB & Golfcart

BOOKING SUMMER 2026 HOST PAYS AIRBNB FEE ! SPECIAL 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 proximity/ steps to the beach

Beachfront Sanibel Condo

Enjoy beautiful Loggerhead Cay, a beachfront development on Sanibel Island. This second floor unit is in pristine condition, suffered no Ian damage and is perfect for a family getaway at the beach. Loggerhead Cay is centrally located on Sanibel, has a wonderful pool, multiple beach access points, and amenities like grills, tennis, pickleball and shuffleboard. See why many people love Loggerhead Cay, and come year after year to enjoy the beautiful sandy white beaches of Sanibel Island.

The Flamingo Residence at Sandpiper Inn

The Flamingo Residence is a one bedroom, one bath, unit located in the newly renovated, Sandpiper Inn. Festooned with gorgeous palm trees and an ever present ocean breeze, The Sandpiper Inn has been coveted by travelers as the most colorful inn on Sanibel. Close to beaches, dining and shopping, this property boasts one of the best locations on all of Sanibel Island. NEW: dog enclosure for our 4-legged guests to play while you enjoy our outdoor seating areas with grill and fire pit!

Stunning Luxury canal front villa across the beach

Escape to your perfect waterfront retreat! This charming two-bedroom, one-and-a-half-bath canal-front home offers stunning views of a wide canal where manatees and dolphins are frequent visitors. Enjoy peaceful mornings and breathtaking sunsets right from your backyard. Ideal for outdoor lovers, the property is perfect for fishing and kayaking, with direct canal access just steps away. And for beach enthusiasts, the sandy shores are conveniently located directly across the street

Modern City Loft in Downtown River District

Welcome to Gun-Loft, a custom-designed modern sanctuary in the Downtown River District. This expansive 3500 square foot city loft is tailored for those seeking to embrace the cosmopolitan lifestyle, with the perfect blend of urban luxury and cultural richness. Whether it's a leisurely stroll to the Edison Ford Home, an exciting night out, or a culinary adventure in the restaurants nearby, Gun-Loft offers an unparalleled experience in the city's most coveted location.

BRAND NEW Luxury Villa w/Heated and Chilled Pool

Brand new high-end 3 bedroom 3 bath designer home, elegantly decorated with incredible views and direct no-bridge Gulf access. Come and make your lifetime memories in this elegantly appointed executive villa. Located near Matlacha, Sanibel, Fort Myers, and Naples. Extra wide canal with only trees opposite, a salt water lagoon, and just off the spreader canal means incredible solitude and privacy in your elegant oasis retreat.

Dive into Luxury: Stunning Tropical Home & Pool

Escape to a tropical paradise in this stunning 1952 midcentury modern home, perfectly located in the heart of historical McGregor Boulevard - home to the famous palm trees planted by Thomas Edison. Indulge in delicious meals at local restaurants like McGregor Cafe and McGregor Pizza, or tee off at the nearby public golf course. And if you're looking to hit the beach or explore downtown, both are just a short drive away.

Waterfront Pool Home. Minutes to Sanibel & Beaches

Where prime location meets tropical paradise. Welcome to your very own lakefront, poolside oasis, less than 10 minutes from the beach! Close to Sanibel Island, Fort Myers Beach & Bunche Beach, as well as local shopping, amazing restaurants, fun nightlife in Downtown Fort Myers and the winter homes of Thomas Edison & Henry Ford. Fully renovated throughout. The perfect destination for a family or friends vacation!