Vacation rentals in Pirates Cove

Cozy 2 br/2 bath home in Cudjoe

Discover a slice of Floridian paradise in our charming 2b/2bath located in Venture Out community, Cudjoe Key. Two bedrooms and an outdoor patio promise relaxation, while community amenities such as a pool, tennis courts, and kids' playground are available. A place to experience the laid-back Florida lifestyle and create unforgettable memories. Book your stay with us today and come live the dream in Cudjoe Key! ****Upon entry, there is a one-time community fee paid at the gate check-in: $125.

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.

Rise And Shine On The Water

Spectacular sunrise view! Room to park one vehicle & have a free overflow lot if needed. Community amenities include tennis, pickle ball, bocce ball, heated pool, hot tub, designated swim area, pool table, ping pong, & darts. We provide bedding, towels, pots & pans., GRILL, TV in living room & one bedroom. We will also have boat bumpers installed all along the concrete dock that will accommodate a 40' boat. We offer 100% money back if your rental is in the projection cone of a named hurricane.

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.

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.

Relaxing Home in the Keys

This 2 bedroom, one bath home is located in Venture Out on Cudjoe Key, FL. 23 miles outside Key West!. Venture Out is a gated community that features, community pool, hot tub, tennis courts, basketball court, a private ramp, unit is 85 yards from ramp, easy for lunching kayaks. There is a dishwasher, grill, TV and free WIFI. The unit includes 2 adult bikes, 2 person Kayak and Paddle board at no extra chargeATTENTION: The community charges a non-refundable security/registration upon arrival.

Dolphin Daydreams 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. ** DOLPHIN DAYDREAMS is a freshly built 2-bedroom tropical home specifically designed to be the perfect antidote to the stresses of everyday life. Substitute zoom meetings and rush hour traffic for slow mornings on the patio and afternoons in the sun. Nestled within Venture Out, a popular resort community on Cudjoe

Oceanside home 111, dock,kayaks,bikes,pool,fishing

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #111 and I also rent adjacent homes 109 and 107 in case you need more than one. We are 40 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

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!

The Lighthouse - Beach Houses Key West

If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

Palm Breezes! Room for Everyone on the Ocean.

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.