Vacation rentals with a patio in Sunset Key

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Top-rated patio rentals in Sunset Key

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Guest favorite

Condo in Key West

4.95 out of 5 average rating, 158 reviews

Fully renovated 2/2 bath condo w/ shared pool!

**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

Top guest favorite

Apartment in Key West

5 out of 5 average rating, 23 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!

Guest favorite

Cottage in Cudjoe Key

4.93 out of 5 average rating, 135 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Superhost

Vacation home in Key West

4.87 out of 5 average rating, 330 reviews

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.

Guest favorite

Houseboat in Key West

4.95 out of 5 average rating, 128 reviews

Amazing houseboat with a sunset eco-trip included

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Garrison Bight Marina in Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

Top guest favorite

Cottage in Key West

4.86 out of 5 average rating, 7 reviews

NEW! - The Jolly Rooster Cottage - Walk to Duval

We’re thrilled to welcome you to our newly renovated, standalone cottage. Nestled just one block from vibrant Duval Street, you’ll be steps from Key West’s best dining, shopping, and nightlife Thoughtfully designed for relaxation and comfort, the Jolly Rooster comfortably hosts up to six guests and blends island charm with modern convenience. Our cottage comes fully equipped for a memorable stay. Come unwind, explore, and experience the best of island living at the Jolly Rooster!

Top guest favorite

Houseboat in Key West

4.96 out of 5 average rating, 26 reviews

Shanty Pineapple Key West

Indulge in an unforgettable, sensual escape aboard our private off-grid houseboat in Key West. Perfect for couples seeking to reignite passion or explore new adventures together, this secluded floating retreat offers an intimate, exclusive setting where every moment is infused with romance and possibility. Whether you’re here to reconnect, explore each other’s desires, or simply escape the world, the serene waters and intimate atmosphere make this the ultimate romantic playground

Superhost

Home in Cudjoe Key

4.86 out of 5 average rating, 105 reviews

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

Superhost

Villa in Marathon

4.9 out of 5 average rating, 344 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Guest favorite

Home in Summerland Key

4.91 out of 5 average rating, 100 reviews

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!

Guest favorite

Houseboat in Marathon

4.89 out of 5 average rating, 122 reviews

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

Top guest favorite

Home in Marathon

5 out of 5 average rating, 41 reviews

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

🏝️ Oceanfront Luxury - Brand New $4M, spacious 5-bedroom, 4.5 bath home 📍 Prime Location - Minutes from Sombrero Beach, top restaurants, island bars, and boutique shopping 🔥 Free Heated Pool - With gorgeous ocean views ⚓️ Private Marina Access - 38 ft protected boat slip 🏈 Includes NFL Sunday Ticket - Get every game ✅ Hassle Free Checkout - No chores, no stress. Just pack and go.