
House vacation rentals in Sunset Key
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Top-rated house rentals in Sunset Key
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Gorgeous Romantic Private Villa, Steps from Duval!
Located 20 yards from historic Duval St in the heart of Old Town Key West w/ free ... first-come, first-serve PARKING in front (4 spots). Totally remodeled, beautiful spacious & private 2 story villa sleeps 4 comfortably. New furnishings, free hi-speed wifi, 65" smart tvs, ice machine, electric fireplace in large master suite, lush garden courtyard & shared plunge pool. We provide 2 coffee/tea stations. Walking distance to everything - convenience store, CVS, bars, restaurants & entertainment.

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!

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***

Near Duval: Hot Tub, Sleeps 6, Top Location
Just 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bedrooms, one bathroom, a full kitchen, and private outdoor perks—like a hot tub, second-story sundeck, and outdoor shower—you’ll have everything you need to relax in paradise. Ideal for up to 6 guests, it’s a tropical haven steps from world-class dining, shopping, and beaches. Book now and soak up the island life! Don’t forget to click the ♥ to save it for later.

3 Bedroom Home - Perfect Location & Private Pool
The historic William Skelton Home is ideally located on Eaton Street in Old Town Key West, steps from Duval Street and all major attractions. This rental listing includes the second and third floors of the home, which features three bedrooms, a private swimming pool, spacious living areas inside and outside, off-street parking, and a newly renovated chef's kitchen to prepare meals. The first story of the home will be left vacant when this listing is rented.

Palm Breezes! Room for Everyone on the Ocean.
This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

Waterfront Anchor 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 Haven 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!

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Pilar House
Charming 3BR/2BA townhouse in the heart of Old Town Key West. Just steps from restaurants, bars, shops, and attractions, yet on a quieter street for a relaxing stay. Two queen bedrooms downstairs, a king master with a balcony upstairs, plus a queen sofa bed to sleep 8. Enjoy a large private deck perfect for morning coffee, lounging, or BBQs. The ideal mix of comfort, space, and unbeatable walkability.

Paradise found
Located on Stock Island this 3 bedroom home is only 8 minutes from Duval street. Walking distance to several great restaurants. Gated community with a gym and large resort style swimming pool. Queen bedroom on first floor with full bath. Second floor King room with private full bath. 3rd bedroom as two twin beds beds with private full bath.

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute
Charming 3-Bed, 3-Bath Home in Gated Community Spacious standalone home with stunning views of the free-form pool. Enjoy the breeze from your private porches in a secure, peaceful setting. A perfect blend of comfort and privacy!

Lennon's Lodge, Luxury Accommodations for up to 6!
Sophisticated tropical decor with top of the line furniture and amenities. 2 K Tommy Bahama bedrooms, Q sleeper sofa, full kitchen, tumbled marble shower, private rear deck with private 7 person spa and 2 person outdoor shower.
Popular amenities for Sunset Key house rentals
House rentals with a pool

Pelican's Roost, Waterfront comfort at Venture Out

Serenity Now Seaside Escape - Brand New Build!

Cudjoe Key Home with a View

106- Newly Renovated House with Oceanview and Pool

Ocean Front Home in Great Location

JUNE/JULY Save$ Oceanfront 4 BIKE/2Kayak. KING bed

Fisherman's Paradise Cudjoe Key

Island Oasis ~ YOUR Paradise Awaits!
Weekly house rentals

Kelly’s Kabin - Private FL Keys Cottage

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

Charming 2BR | Hot Tub | Deck | W/D

Starlight Serenity - Hideaway with Stunning Views

Island Villas Rentals

Pool-2 HotTubs-Boat Lift-Easy Access to Gulf&Ocean

Cozy house with relaxing pool

The Hideaway - Private Paradise at its Best!
Private house rentals

Gone Coastal

Powell Family Resort

Gone Coastal 2

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

Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!

Waterfront Haven House with Boat Basin & Ramp!

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

Waterfront FL Keys Cottage @ Venture Out
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- Sombrero Beach
- Smathers Beach
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- The Turtle Hospital
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Key West Aquarium





