Cottage holiday rentals in Key West

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.

2Bd/1Ba Waterfront Retreat w/35’ Dock

Discover the FL Keys in this bright & beachy 2-queen bed, 1-bath waterfront modular home in Venture Out on Cudjoe Key. Enjoy your fresh catch in the full kitchen, laundry in-house, nice wide canal with 35’ dock for your boat just steps from your door. Indulge in unparalleled amenities & scenic beauty: oceanfront pool, hot tub, marina w/marine fuel, wash station, store; tennis, bball, pickle ball, & playground. $125 add’l resort fee paid direct to Venture Out at gate. Incl Bikes & kayaks for use.

Tidewater 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. ** TIDEWATER VIEWS is a cozy 800 square foot cottage that has everything you want for the perfect tropical vacation: open water views from a covered porch, a private 35-foot boat slip, kayaks, bikes and access to the wonderful amenities at Venture Out Resort: a heated 80-foot pool with large Jacuzzi and Kiddie Pool,

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.

OCEANIA... water front cottage retreat ~

OCEANIA... water front cottage retreat ~ Completely remodeled, direct cannal-front cottage offers everything you'll need for the perfect getaway. Boat dock (35ft), HD Smart TVs, washer & dryer, S/S appliances! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

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!

NEW! - The Jolly Rooster Cottage - Walk to Duval

We’re thrilled to welcome you to our newly renovated, standalone cottage. Nestled just one block from vibrant Duval Street, you’ll be steps from Key West’s best dining, shopping, and nightlife Thoughtfully designed for relaxation and comfort, the Jolly Rooster comfortably hosts up to six guests and blends island charm with modern convenience. Our cottage comes fully equipped for a memorable stay. Come unwind, explore, and experience the best of island living at the Jolly Rooster!

Keys Waterfront Oasis • Tiki • Private Pool • Dock

Lilo's in The Keys, a tropical paradise! This cherished waterfront gem has been a beloved destination for years. The perfect getaway to unwind and indulge in the island lifestyle. Nestled among tropical landscaping, Lilo’s boasts a private saltwater pool, a tiki patio for outdoor lounging and a dock for your boat. Your stay includes kayaks, so you can explore the beauty of Key Colony Beach at your own pace. The home is fully equipped with all the comforts of home.

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.