
Pet-friendly holiday rentals in Sunset Key
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Top-rated pet-friendly home rentals in Sunset Key
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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.

Cottage 30 min from Key West, free parking, pool
Escape the everyday and unwind under the stars in this charming, nature-surrounded getaway where deer are frequent visitors. This cozy tiny house of offers 1 bedroom, 1 bathroom, and 3 beds, comfortably sleeping up to 4 guests. Enjoy peaceful surroundings, fresh air, and convenient double parking with space for a truck and boat trailer—perfect for outdoor adventures and total relaxation. Ideal for couples, families, or friends seeking quiet nights, wildlife views, and a simple, memorable stay!

Palm - Beach Houses Key West
If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Experience the charm of our recently renovated, one-of-a-kind two-bedroom beach bungalow, nestled right on the shore. Enjoy breathtaking ocean views from your private deck, relax on the sandy beach, and soak in the tropical ambiance. This family-friendly retreat offers the perfect setting to make you feel like you’re on your very own private island.

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.

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage
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, & building elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

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***

Key West Studio a short walk from Higgs & Duval
This clean, cozy studio is located in old town, just a 10 minute walk to Higgs Beach and a 15 minute walk to Duval St. Grab a bike from the backyard and explore all Key West has to offer. You are close to all the great local restaurants and shops. There is also a full kitchen if you and a grill out back perfect for a BBQ. There is a washer/dryer on site. There is snorkeling, boat tours, fishing, and water sports nearby. (Bikes may need some work done, shop is close)

Waterfront Haven House with Boat Basin & Ramp!
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). 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 point and enjoy the underwater scenery!

Duval Corner - Pet friendly with Balcony
Welcome to Duval Corner! A beautifully updated one-bedroom condo in the heart of Downtown Key West. This second-floor retreat is perfect for travelers wanting to be steps from it all. Within walking distance to iconic attractions like the Southernmost Point, The Ernest Hemingway Home, and Mallory Square, plus dining hotspots such as Blue Heaven, 7 Fish, and Louie's Backyard; Duval Corner is the ideal base for your Key West adventure.

The Dancing Rooster - 1 Block to Duval!
Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions.

Classic 30’ Sailboat
A Unique Key West Getaway! Welcome aboard Sparhawk! This beautiful 30-foot Baba double-ender sailboat offers a cozy and unforgettable stay for 2 adults and 2 small children’s . Crafted with warm teak interiors and timeless nautical charm, Sparhawk is perfect for couples, small families, or adventurous souls looking for something off the beaten path.

Your own private resort! Pool, tiki, RV Hookup
**SERENE BAYFRONT PARADISE!** The grounds of this home will take your breath away. This is a unique opportunity to experience the Keys with your own private beach-style backyard lounge, resort-style tiki hut, pool, and 50ft dockage right on the gorgeous Florida Bay with a front row seat for sunset every night. Just 15 min from Duval!
Popular amenities for Sunset Key pet-friendly home rentals
Pet-friendly house rentals

Key West Paradise

Oceanfront 2BR in Venture Out - 35’ Dock + Pool

Kelly’s Kabin - Private FL Keys Cottage

Dolphin Daydreams at Venture Out

Amazing Ocean views, 35’ Seawall, Pool and Kayaks

Amelia Home by AvantStay | Old Town Home w/ Pool

Casa Cove 3bed3bath sleeps 8 beautiful decorated

Catherine House: A charming Old Town Key West
Pet-friendly home rentals with a pool

43' Classic Yacht Views, Pools, Duval Shuttle

Romantic Captain's Quarters

Ocean Front Home in Great Location

RV In The Keys | Tropical Retreat

Tropical Island Getaway

2BR Suite | Pool | Hot Tub | Tennis | Dog Friendly

Location Location Beach Paradise in the Keys Duval

Waterfront FL Keys Cottage @ Venture Out
Private, pet-friendly home rentals

Waterfront Cozy Cottage with Boat Ramp & Dock!

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

Honeymoon Hideaway, King bed, Private Deck & Spa!

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

Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"

Deluxe Bungalow

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

Lennon's Lodge, Luxury Accommodations for up to 6!
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