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Islamorada bungalow 2 bed & pool

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

Beautiful Cottage & Amenities in Gated Community

Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

Charming 2BR cottage in prime keys location w/pool

Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

Waterfront Cottage Walk to World Famous Lorelei

Waterfront Conch Cottage with Dockage. Short walk to world famous Lorelei for sunset celebrations. Great location for kayaking & paddleboarding. Custom length of stays can be arranged if booking a sandbar/fishing charter with our family. The fishing cottage built in the 1940s is not fancy, as photos show, but in the heart of Islamorada! Dockage available for additional $25 per night fee not included in nightly rate. Free trailer storage on site. Pet friendly :) 1 pet under 20 lb $150 fee.

Turtle Cove Views at Venture Out

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** TURTLE COVE VIEWS is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the expansive open water views from inside the home through the large windows or from your covered porch, with outdoor dining. The private 35-foot boat slip offers easy access to the beautiful waters of

Old Town 2-Bed/2 Bath Cottage & Pool

28-night minimum stay rental. Located in a neighborhood 3 blocks from Duval & a short walk or bike ride to Higgs Beach, Southernmost, bakeries, galleries, & Cuban coffee. Cottage has a fenced yard, pool, & two covered porches overlooking the front & back gardens. Our home is on the ground floor of the house. Our full-time tenant lives in a detached studio, accessed by a side entrance & stairs at the rear of the property. Airbnb guests have exclusive use of porches, pool, & deck.

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Waterfront cottage w/ MotherInLaw suite&boat slip

The property is on the Bay, with a balcony in the palm trees and a large back porch on the water. Includes a ComPac sailboat, use of kayaks, bicycles and BBQ grill. Boat slip included! Located at Mile Marker 63, on Conch Key, the location is convenient to all Keys attractions: Key West, MM zero, State Parks, Museums, shopping, snorkeling and diving, and some of the best fishing in the world.

Enjoy Tropical Experience in Beachfront Casita

Escape to laid-back island living at La Siesta Resort & Villas in Islamorada. Set on a private beachfront with tropical cottages, enjoy poolside cocktails at Sidecar, kayak and paddleboard rentals, and shared access to sister resorts via water taxi or shuttle. Ideal for families, couples, or groups seeking a serene Keys getaway.

Hidden Key West Cottage • Walk to Duval

🌴 Welcome to your hidden Key West escape Tucked away in Old Town, this private cottage puts you just steps from Duval Street—close to everything, yet quiet enough to truly relax. Perfect for couples or solo travelers looking for a peaceful retreat in the heart of Key West.

Island Style - the only way to vacation!

This quaint property offers resort-style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages, amid lush tropical landscaping, sits Island Style, the sister cottage of Hidden Treasure.