
Vacation rentals with a kayak in Stock Island
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Top-rated kayak rentals in Stock Island
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Coconut Mallory. Waterfront & Key West charm.
The Coconut Mallory Resort and Marina offers island-style relaxation set amidst lush greenery and scenic waters. Enjoy spacious accommodations featuring a fully equipped kitchen, comfortable living area, and private balcony. Relax at the outdoor pools, hot tub, or enjoy libations at Gumbos, the on-site bar with marina views (currently closed). Marina usage is available. Easily explore all Key West has to offer. Located just 2 miles from Smathers Beach, 3 miles from Duval Street, and 4 miles from

Waterfront FL Keys Cottage @ Venture Out
Welcome to the BEAUTIFUL Florida Keys! The Keys Cottage 116 is a cute 2 bed, 1 bath home ON THE WATER in the desirable and SAFE Venture Out community on Cudjoe Key just 20 minutes from Key West. Starting at $195/night with weekly & monthly discounts & NO fees for EXTRA GUESTS! The amenities are INCREDIBLE! Large pool, hot tub, kiddie pool, PICKLEBALL, tennis, Bball, marina, 24 hr security, store, boat launch ramp, etc. We can do NIGHTLY rentals & WE ALLOW PETS, all for much less than a hotel.

2Bd/1Ba Waterfront Cottage w/35’ Dock
OCT DISCOUNTS! Discover the FL Keys in this bright&beachy 2-queen bed, 1-bath waterfront home in Venture Out on Cudjoe Key. Enjoy your fresh catch in the full kitchen, easy laundry in-house, &nice wide canal to dock your boat on-site. Indulge in unparalleled amenities & scenic beauty: oceanfront pool, hot tub, marina (marine fuel, wash station, store), tennis, bball, pickle ball, &playground. $125 add’l resort fee paid direct to Venture Out at gate. Includes Bikes&kayaks available for your use.

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Amazing houseboat with 2nd floor observation deck
Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Garrison Bight Marina in Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

Waterfront Sanctuary in the Keys!
Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

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***

Oct. & Nov. 50% off! Oceanfront, 4 Bikes 2 Kayaks
*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Houseboat Getaway In Marathon
Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Poolside Paradise
The whole group will enjoy easy access to everything from this centrally located two bedroom/2bath home with a private heated pool. Poolside Paradise is only 1/2 block from world famous Duval Street, walkable to almost everything you may want to do in Key West.

Beach Club Ocean Front 2BR Condo
Come fall in love with Key West in our luxurious ocean front condo. The Key West Beach Club is located directly on the Atlantic in a quiet residential secured building. It is a 2BR, 2 1/2 Bath located in Mid-Town.
Popular amenities for Stock Island kayak rentals
House rentals with a kayak

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Blue House - Receive $400 towards a Boat Rental!

Living In Beautiful Paradise

Ocean Front Home in Great Location

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

Piner's Retreat

Turtle Cove

Pelican's Paradise #507 - Gated Community!
Cottage rentals with a kayak

OCEANIA... water front cottage retreat ~

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Ocean Breeze @ VO - Kayaks, Bikes, 30 Min from KW

Calypso Cottage
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Adventurers escape breathtaking off-grid houseboat

Charming Houseboat in Key West

Beach house in the Keys

Yellow Home - Receive $400 towards a Boat Rental!

Duval street downtown

Ocean Mist

Tropical Paradise

Blue Palms Retreat
Quick stats about vacation rentals with a kayak in Stock Island
Total rentals
20 properties
Nightly prices starting at
R1,911 ZAR before taxes and fees
Total number of reviews
730 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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