Pet-friendly holiday rentals in Sunset Key

Catherine House: A charming Old Town Key West

This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, and shops. Catherine House is located only ½ block from the quieter end of Duval Street, and better yet, just three blocks to a beach (Duval and South Streets). The house can comfortably sleep four and offers a fully equipped kitchen, two bedrooms, two full baths, and a small pool. There is a washer and dryer located in a shed behind the house. A covered front porch offers a pleasant

Key West Cottage Du Soleil w/ Pool!

This two-bedroom Key West Writer's Cottage is a serene haven for creative minds and vacationers. It features a cozy living area with charming decor that inspires relaxation. Enjoy the relaxing deck for morning coffee or unwinding with a book, and take a refreshing dip in the inviting pool. Each comfortably furnished bedroom ensures a restful night’s sleep, and the fully equipped kitchen is perfect for cooking. Plus, you can easily bike to the nearby boardwalk and beach for fun in the sun!

Casablanca Too ~Chicly updated home with hot tub

On the edge of Historic Old Town and tucked in a residential neighborhood, Casablanca Too is a great place to enjoy the fun, carefree vibe of Key West. This 1 bedroom/1 bath duplex was recently redesigned and will meet all your needs while away from home. **This home is available in August only as a monthly rental (28 nights in the same month).** Come and live like a local! THE PROPERTY: Enjoy fresh air and sunshine from your front porch or backyard hot tub at Casablanca Too.

"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***

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!

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.

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.

Oceanfront Bungalow Venture Out

Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water ...incredible views. 52' concrete dock/seawall complete with dock posts and fishing table. Lovely decor. Bocce ball, playground. Tennis, Hot Tub, 2 pools. Recreation center with billiards, darts, and ping pong. Post Office and a Library 24 Hour Gated Security. . 40" screened TV. WIFI Saturday to Saturday only 7 night minimum.

Casita de Catherine by AvantStay | Patio + Hot Tub

★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-tier stays. - Cute Cottage - Hot Tub - Spacious Patio - 1 Block to Duval Sreet - Near the famous La Te Da restaurant and bar

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.

Cottage 30 min from Key West, free parking, pool

Get away from it all when you stay under the stars in this amazing little gateaway, surrounded by nature and amazing deers . This is Tiny house with 1 bedroom, 1 bathroom and 3 beds, accommodating up to 4 people!