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Waterfront holiday rentals in Stock Island

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Stock Island

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Apartment

4.83 out of 5 average rating, 257 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

La Dolce Vita is a one bedroom, one bath condo with granite galley kitchen, living room, newer a/c, flooring, located in the heart of the Historic District in Old Town and is walking distance to all the shops, restaurants, bars and just steps to Duval Street! You will not need a car with this location. Large wraparound balcony with sitting chairs & table. Extra cleanings for an extra charge Southernmost Beach is just 3 short blocks away. Southernmost Point, Hemingway House, Butterfly World.

Houseboat

4.83 out of 5 average rating, 282 reviews

Key West Houseboat Paradise

282 reviews over 5 years! SuperHost Rated! Queen Bed, Full Kitchen, Big Living Rm, Full Bath & 3 Sun Decks. Completely rebuilt in 2022. 15 min from downtown, tucked away on a wooden dock. The vibe is 'Old-School Key West'. The property has a light-industrial feel with a 2-bay auto garage & a warehhouse, so the shore side isn't fancy but the Back Deck View is a mile-wide ocean channel with dozens of bright green mangrove islands and a pair of Sea Kayaks just waiting for you to go exploring.

Guest favourite

Cottage

4.9 out of 5 average rating, 155 reviews

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!

Guest favourite

Boat

4.86 out of 5 average rating, 151 reviews

ALL INCLUSIVE! Snorkel/Sail/Spear Fish/Fishing/Fun

You will love staying on this 45' GulfStar Sloop. The boat boasts 2 BR, 1.5 bath with shower, full working galley, A/C throughout and plenty of room to relax down below. Every reservation comes with a sunset sail along with day sailing, snorkeling or fishing. Layout and be lazy on the spacious deck or whatever you would like to do! Visit SailAway GetAways on FB for more detailed view. **Unfortunately one night reservations do not allow time for excursions. Except a sunset sail.**

Guest favourite

Apartment

4.9 out of 5 average rating, 174 reviews

Large waterfront 2/2 end unit with boat slip

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & private elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

Guest favourite

Home

4.97 out of 5 average rating, 138 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Guest favourite

Home

4.99 out of 5 average rating, 119 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Home

4.82 out of 5 average rating, 243 reviews

OCEAN PARADISE AT VENTURE OUT + 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!

Guest favourite

Townhouse

4.91 out of 5 average rating, 125 reviews

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

Rental unit

4.92 out of 5 average rating, 178 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

1357 s f Luxury beachfront resort condo w/ all the amenities - beachfront heated Olympic pool, 3 lighted tennis courts, 20 man hot tub, tropical gardens, beach, saunas, Gym, BBQ Grills everything to make your vacation spectacular! You must be at least 25 years old to rent this property. This is a no animal rental due to extreme allergies of the owner. Thank you for understanding

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Popular amenities for waterfront rentals in Stock Island

Free parking on premises

Air conditioning

Waterfront apartment rentals

Guest favourite

Rental unit

5 out of 5 average rating, 9 reviews

"O" Fish Ally Paradise @Ocean Isle Fishing Village

Rental unit

5 out of 5 average rating, 8 reviews

New Deluxe Duplex Unit, 2 Queen Beds, Unit H-5

Rental unit

5 out of 5 average rating, 4 reviews

Partial ocean view studio with king bed

Rental unit

4.83 out of 5 average rating, 96 reviews

Beachside Unit 22 - Private Beach on Atlantic

Guest favourite

Rental unit

4.95 out of 5 average rating, 19 reviews

Key West Condo with Pool & Boat Slip Access

Guest favourite

Rental unit

5 out of 5 average rating, 11 reviews

#1 Island Hideaway 89 - OCEAN FRONT

Guest favourite

Rental unit

5 out of 5 average rating, 7 reviews

Best Catch on Grouper LN at Ocean Isles

Guest favourite

Rental unit

4.96 out of 5 average rating, 49 reviews

Dock POOL Kayaks Bikes Beach2mi WalkToStores

Waterfront house rentals

Guest favourite

Home

4.96 out of 5 average rating, 24 reviews

Waterfront 35’ Dock,80’ pool,20 min Key West

Guest favourite

Home

4.9 out of 5 average rating, 145 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

Home

5 out of 5 average rating, 3 reviews

Secluded Waterfront Oasis in the Keys

Home

4.81 out of 5 average rating, 27 reviews

Yellow Vacation home, Free cancelation see details

Guest favourite

Home

4.98 out of 5 average rating, 110 reviews

Super Nov. Savings! Key Colony Beach, Cabana Club

Guest favourite

Home

5 out of 5 average rating, 18 reviews

Nautical Wheeler: Waterfront Home with private Poo

Guest favourite

Home

4.95 out of 5 average rating, 123 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

Guest favourite

Home

4.91 out of 5 average rating, 127 reviews

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

Waterfront apartment rentals

Apartment

4.73 out of 5 average rating, 144 reviews

2 Bedroom Oceanfront Complex Heated Pool KCB

Guest favourite

Apartment

4.94 out of 5 average rating, 33 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

Apartment

5 out of 5 average rating, 4 reviews

Galleon-Walk to Duval & Mallory Square!

Guest favourite

Apartment

4.95 out of 5 average rating, 20 reviews

Paradise Palms 1B/2B Desk; Pool; Balcony

Apartment

4.83 out of 5 average rating, 6 reviews

Vista Fresco at Oceanside Condo Community

Apartment

4.78 out of 5 average rating, 63 reviews

Casa Papa Del Mar on the Atlantic Spectacular view

Guest favourite

Apartment

4.98 out of 5 average rating, 85 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

Guest favourite

Apartment

4.82 out of 5 average rating, 34 reviews

Henry's Piece of Paradise On The Ocean In Key West

Quick stats about waterfront rentals in Stock Island

Total rentals
40 properties
Nightly prices starting at
£85 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
30 properties have a pool

Destinations to explore