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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.

Welcome to Paradise, Private Pool, SUPs, Kayak!

Paradise Awaits You!! With a Beautiful Private Pool, 40’ Dock, Kayaks, SUPs, & Bikes; Welcome to Paradise is the Perfect Place to Stay & Play in the Sun & on the Water! Our home w Breezy Palms is centrally located w Beaches, Boating, Fishing, Diving, Swimming, Dining & Refreshing Cocktails just minutes away! We are owners, Luis & Aysie. We put all our love of the Keys into our home, & we just know you will love it too. Message us or book instantly & start planning your trip to Paradise!

Palm - Beach Houses Key West

If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Experience the charm of our recently renovated, one-of-a-kind two-bedroom beach bungalow, nestled right on the shore. Enjoy breathtaking ocean views from your private deck, relax on the sandy beach, and soak in the tropical ambiance. This family-friendly retreat offers the perfect setting to make you feel like you’re on your very own private island.

Island Paradise

*** Please note: There is a one time registration fee of $125 to be paid at gate*** Cozy keys getaway w/ ocean front heated pool, boat ramp and more. Relax in this 1 BR, 1 BA manufactured home in a resort style park with heated pool, hot tub, boat ramp, sports courts and walkable dining. This clean well kept home features a king bed in primary BR and queen gel memory foam pullout sofa in living room. Fully stocked kitchen! Hair dryer, shampoo, conditioner, bath soap, etc. are furnished.

Grouper House: 4 Masters/6 BA, Pool/Dock, BoatRamp

Welcome to Grouper House, a stunning canal home w/ 4 Master Suites, King beds, private ensuite baths, in-room wine and coffee bars, smart TVs, and patio access. The open-concept kitchen/dining/living area includes a 55-inch smart TV and half bath. A covered porch overlooks a large saline pool w/ splash deck. Poolside is a shaded outdoor grill area w/ a sink, extra fridge, commercial icemaker, bait freezer, shower and 1/2 BA. The IPE dock has a fish-cleaning station and a private boat ramp.

P08 - Beautiful 4 bedroom, 3 bath with Cabana Club

Now offering Cabana Club Membership! This lovely two-story half duplex in Key Colony Beach offers 4 bedrooms, 3 bathrooms and abundant living space on both levels. The upper level offers 2 bedrooms, 2 bathrooms, a kitchen with oversized breakfast bar and abundant living space. The lower level offers 2 bedrooms, 1 bathroom, a kitchenette and den. Key Colony Beach offers a par 3, nine-hole golf course, public pickle ball courts, Sunset Park, several restaurants, clothing boutiques ...

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

Steps to the Ocean & Heated Pool

Escape to paradise in a new 1 bed/2 bath centrally located in Marathon. Our condo is steps away from open ocean views, where you can fish off the docks, lounge under one of the many Tiki huts, or cool off in the vast elevated swimming pool that overlooks the Atlantic. Fully air conditioned clubhouse on property is equipped with a commercial ice machine. Convenient grilling stations located next to the clubhouse, to cook your fresh catch. Come enjoy paradise. VACA-23-312

Waterfront Haven House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). 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 point and enjoy the underwater scenery!

Fun in the Sun in Cudjoe Key! #51

This beautifully updated stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you to come and relax. VENTURE OUT COMMUNITY REGISTRATION FEE OF $125.00 IS DUE UPON ARRIVAL IN CASH OR CREDIT CARD ONLY.

The Lookout #659 Venture Out - Gated Community

Welcome to The Lookout #659 at Venture Out on Cudjoe Key! Experience your perfect getaway at our stunning high-rise vacation rental, this beautifully decorated 2 bedroom, 2 bath home offers the ideal blend of comfort and style, with a coastal-inspired decor that invites relaxation and rejuvenation. Resort style amenities here at Venture Out!