Holiday rentals in Wisteria Island

4.81 out of 5 average rating, 322 reviews

Houseboat in Key West

Key West Houseboat Paradise

5 Years SuperHost Rated with over 300 reviews!! ~ Single Stateroom with Queen Bed, ideal for a couple. Sleeps 1-4. Spacious living room, big sofas. Full kitchen, Full Bath, large Rooftop Sun Deck, 15 min to Duval St. The land-side isn't fancy. Light industrial, Old-school Key West feel. Blue collar, friendly working class, wooden dock with a working auto garage & warehouse but the water view of dozens of green mangrove island with 2 Sea Kayaks waiting for you to take exploring is a Hidden Gem.

5 out of 5 average rating, 10 reviews

Apartment in Key West

Coral Palms 1BR/King/Queen, Pool, block to Duval

Escape to this charming 1BR, 2nd-floor condo in the heart of Historic Key West. Sleep soundly in a plush king bed and additional guests in a Queen & sofa bed in a spacious living area and a fully equipped kitchen. Lounge poolside under the palms, grill, or relax in the refreshing pool. No transportation needed, you're just steps from lively Duval Street, world-class dining, nightlife, and beaches. Perfect for a romantic getaway or a fun retreat, your island escape awaits! Hosted by Nautipussy!

4.77 out of 5 average rating, 363 reviews

Key West - Sunrise ❀ The Green House

Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable price and enjoy! ♡ Best location for exploring Key West, in the epicenter of Old-Town and all attractions. One corner from world-famous Sloppy Joe's (Hemingway's favorite place) and Duval Loop, the free local ride. Check out the map and see all attractions right around The Green House!

5 out of 5 average rating, 14 reviews

Heron Hideaway

Welcome to our unique and charming Airbnb. This cozy retreat offers the perfect blend of comfort and style, featuring a private porch where you can relax and enjoy the island breeze. Take a dip in the refreshing pool or unwind in the private hot jacuzzi after a day of exploring. Enjoy cooking a delicious meal on the grill, and experience a peaceful stay in a one-of-a-kind space. Whether you're here to relax or explore, our home provides everything you need for an unforgettable Key West getaway!

4.93 out of 5 average rating, 111 reviews

Apartment in Key West

WALK TO BEACH, MALLORY SQUARE, DUVAL STREET

Key West a little piece of the Caribbean, always warm with lovely turquoise waters. It's a short walk to Mallory Square, Hemingway's Home, the Truman White House, Duval Street. You're just a walk away from Zachary Taylor Park (where you can do yoga on the beach, swim, snorkel, or hang hammocks between the palms). We’re near numerous shops, restaurants, and museums. Enjoy coffee in the morning, wine at night on our oversized deck. THE ADJACENT UNIT MAY BE AVAILABLE FOR ADDITIONAL SPACE.

4.87 out of 5 average rating, 323 reviews

Holiday home in Key West

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

Houseboat in Stock Island

4.96 out of 5 average rating, 23 reviews

The Writer's Block- Key West

Discover tranquility aboard this unique floating haven. It's a sleek modern retreat for those who crave space to read, write or find inspiration far from the stresses of the modern world --yet it's steps away from upscale restaurants, two fabulous pools, a gym and so much more. From a king bed to a full-sized shower and kitchenette, you'll enjoy the comforts of home while living directly on the water. Features a large private deck with panoramic views of the marina and its glorious sunsets.

4.88 out of 5 average rating, 1,505 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. Located on a quiet street, it offers a private pool and peaceful stay for vacationers and business travelers. The unit includes a comfy Queen bed, mini fridge, microwave, iron & board, hangers, TV, and AC. Enjoy Key West's warm weather year-round. This special place is close to everything, making it easy to plan your trip. Just a heads-up: Key West’s famous roosters love to strut and crow—part of the island charm!

4.97 out of 5 average rating, 101 reviews

Apartment in Key West

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

4.91 out of 5 average rating, 279 reviews

Starr's Suite - 2 person K Suite w/Private Spa!

Starr's Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, granite counter-tops in kitchen with dishwasher and vanity. Tommy Bahama bath amenities are provided, as well as coffee, creamer and sugar. 56” Smart TV (bring UN/PW for Netflix, Amazon, etc. to watch your favorite shows). Private Solana spa in your private courtyard. Daily housekeeping is provided. Use of 2 heated pools.

4.96 out of 5 average rating, 280 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Cozy condo in the Truman Annex to fully experience the conch life. It is close to Fort Zachery Beach and State Park, Hemingway House, Mallory Square, and Duval Street. Location is perfect due to Island proximity to any event and occasion. My place is a great getaway for couples, solo adventurers, business travelers, and families (with kids).

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Popular amenities for Wisteria Island holiday rentals

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Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Wisteria Island

5 out of 5 average rating, 21 reviews

Honeymoon Palm Suite near Higgs Beach

KrystalRating, 5 stars2 weeks ago

If you are looking for a place to stay that's away from the partying and busy spots this is a great location. Easy walk to the Salute! on the beach, nice garden club to visit, too. Bikes were very convenient, but the heat pushed us to use Lyft often. Private Patio was a wonderful area to wind down, or sit while you want the 30 seconds for your Lyft to pop around the corner. Nice place!

5 out of 5 average rating, 10 reviews

Private room in Key West

Duval street downtown

VictoriaRating, 5 stars2 weeks ago

I loved staring at Juan’s place and will definitely stay here again if I am in Key West. His place is just south of all of the popular bars on Duval Street, which is nice because you’re close enough to the party scene but still pretty far away. I was able to get great sleep and the surroundings weren’t loud at all although there is a restaurant downstairs that plays music until midnight however, Juan provides earplugs, and I did not hear it or have any issues with the music. You can tell that he put a lot of thought and detail into the space such as sleep masks, chargers, full length mirror and a variety of soaps to choose from during your stay. Before I arrived, he sent me instructions, including a video on how to find this place which was spot on. He even has bikes that you can use during your stay which was awesome. I love riding bikes, so this was definitely a highlight of my trip! Thank you Juan for your hospitality!

4.92 out of 5 average rating, 289 reviews

Home in Key West

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

ElizabethRating, 5 stars1 week ago

Naomi's home is perfect. Beautiful setting, perfect location and wonderful people. Would be happy to stay again!

4.95 out of 5 average rating, 319 reviews

Honeymoon Hideaway, King bed, Private Deck & Spa!

EmilyRating, 5 stars3 weeks ago

This was our first time traveling to Key West and we weren’t sure what to expect. I can’t say enough great things about Center Cottage Inn. They went above and beyond our expectations and it was the perfect place to experience a lot of the wonderful things the island has to offer. The cottage we stayed in was fully equipped for all of our needs and was tiny in the best way. It had a lot of great storage, ample towels (both for bathing and the pool), fully stocked kitchen (we opted to make our own breakfast each day), and lots of thoughtful details like a portable speaker, bug spray, charging ports and more. Naomi was super responsive and helpful. We were able to leave our bags on the premises as our departure flight wasn’t until late afternoon. This was a game changer as we were able to enjoy our last day without carrying luggage around. If you want to feel like locals this is the place for you.

4.97 out of 5 average rating, 260 reviews

Home in Key West

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

JRating, 5 stars1 week ago

Possibly the best Airbnb I have ever stayed at, all amenities listed are better than expected. Host and staff were amazing. Could not get a better location in Key West. We were even going to change plans and stay an extra day, but just couldn’t make it work with the timing of our travel. 6 stars😁 Clean, quiet, perfect!

Hotel room in Key West

4.67 out of 5 average rating, 119 reviews

Coastal Comfort | Sunset-watching. Outdoor Pool

DaníRating, 5 stars2 weeks ago

Understand that this listing is a Hilton Garden Inn hotel but worked out perfectly for my trip. Originally booked hotel thru another site & found the same room for cheaper on AirBnB. Great deal. Comfortable room, didn't make it to the beach but the pool was the best part. They have a bar you can order drinks & food from the pool area which was perfect since we missed the nice breakfast they offer. Dont expect a view besides a parking lot but we werent there to stay in the rm. The free shuttle svc every hour made it worthwhile. A couple days in KeyWest this room was perfect for a couple. Book it.

4.95 out of 5 average rating, 342 reviews

Home in Key West

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

ShannonRating, 5 stars5 days ago

Everything was great!! Both pools were close and nice and clean. Perfect location to shops and restaurants.