Holiday rentals with an EV charger in Stock Island

New Luxury Oceanfront House. Hot Tub & Sunset View

Brand new build 2024. This 5 bed/4bath luxury ocean gulf home with boat dock, heated/chilled pool/ spa, paddle boards kayaks, bicycles was meticulously designed and custom built like no other house in Marathon Key. You can see ocean water from every room in the house. and the interior design was chosen to maximize comfort, with a stress-free peaceful setting. Only three homes on this one-acre private ocean gulf lot that has the look and feel of a private island with 400 feet of bulk head

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Ocean Front 2-bed 2 Bath in beautiful Key West

Hyatt Windward Pointe Resort, Key West -- unit 5211: Family friendly 2-bedroom condo, sleeps up to 6 people, has a full kitchen, an outdoor terrace with ocean view. Beautiful pool with outdoor grill area and play courts. Available only for arrival Saturday February 7 thru departure on February 14, 2026. Wi-Fi available to all throughout resort with full 1 gig rates for both uploads and downloads. The entire resort property-size available to all resort guests is approximately 90,000 square feet.

Tiny House | 35 min to KW + Free Parking & Pool

Discover a hidden gem in the Florida Keys with this charming Tiny House, surrounded by nature and the famous Key Deer. Located in the peaceful Breezy Pine RV Resort, it offers a cozy yet spacious layout for the whole family. Relax outdoors on the private patio with sofa and grill, perfect for enjoying the laid-back Keys lifestyle. With all the essentials for comfort and just a short drive to Key West, Bahia Honda beaches, shops and restaurants. This retreat is ideal for relaxation and fun.

The Mini Coconut

Relax with your family at this peaceful location, steps away from the water. The beautiful lagoon that opens up to the Gulf of Mexico can be seen from the front of the home. You can fish, snorkel, kayak, stand-up paddle board and more, just 50 feet from the house. Please note that this is a single unit of a duplex property. It has a separate entrance and private yard for your pleasure. Centrally located, we are minutes away from the airport, restaurants, beach and shopping. VACA-22-371

Hemingway First Floor Townhouse @ Suite Dreams Inn

Suite Dreams Inn is an intimate family-owned boutique Key West Bed & Breakfast in the tranquil upscale Casa Marina Old Town neighborhood, offering oversized suites with luxurious king & queen beds, kitchens, living rooms, 2 pools, 24/7 laundry, free parking, and relaxing outdoor spaces. We are LGTB & pet friendly & will accommodate well behaved children of any age, as well as private clothing optional & traditional guests. Close to the beach, Duval St., jet ski r

Stunning Townhouse * Full kitchen! * Sleeps 6

This property is a rare find! Sleeping 6 and located over 2 floors, its located in the beautiful resort of Santa Maria. The condo itself is overlooking the pool, enjoys 2 stunning balconies with its own outdoor furniture. Fully equipped kitchen, 21/2 bathrooms, TVs and wifi throughout. The property is located in one of the best destinations within the historic old town. Just 2 blocks from Duval Street, and also just 2 blocks from the beach. You really can have it all!

Historic Key West - Turtle House - Sleeps 6

The neighborhood is alive, dynamic, and surrounded by Key West History - unquestionably the most intact Old Town Key West neighborhood on the island. There are excellent restaurants within walking distance, and Duval Street is only two blocks from the property - close enough, yet far enough away! Ft. Zachary Taylor, located only two blocks to the west of the property, is a National Historic Park and boasts the nicest beach with the best sunsets on the island.

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

Ocean Front Suite with Direct Beach Access

Set on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residences. Unwind in the perfect blend of adventure and relaxation in sunny Key West. On property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise. Don’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.

Waterfront, dock, easy ocean access, heated pool!

Keys living at its best! Tropical classy, comfy and private – yet easy access to everything you could want. This 2 bedroom, 2 bathroom home on a quiet dead end street with open views and ocean access (with houses only on one side) in the heart of the heart of the Keys comes with all the amenities, complete with private pool and ample parking. Please contact prior to submitting booking request. Thank you!

Oceanfront Condo in Key West

Key West Beach Club is a serene waterfront oasis located in an upscale gated community within walking or biking distance to the local’s finest spots, including restaurants, beaches, shopping centers, bars and the infamous Duval Street. This complex prides itself for being one of the very few on the island that sits directly on the water.