House vacation rentals in Sunset Key

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Top-rated house rentals in Sunset Key

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Guest favorite

Home in Key West

4.93 out of 5 average rating, 100 reviews

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.

Nov 18 – 25

R9,637 ZAR per night

Guest favorite

Home in Key West

5.0 out of 5 average rating, 40 reviews

Gorgeous Romantic Private Villa, Steps from Duval!

We are located 20 yards from historic Duval St in the heart of Old Town Key West w/ FREE first-come, first-serve PARKING right in front. 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.

Apr 9 – 16

R12,306 ZAR per night

Guest favorite

Home in Key West

5.0 out of 5 average rating, 17 reviews

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

Jul 28 – Aug 4

R17,748 ZAR per night

Superhost

Home in Cudjoe Key

4.9 out of 5 average rating, 104 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Aug 17 – 24

R7,569 ZAR per night

Guest favorite

Home in Key West

4.98 out of 5 average rating, 48 reviews

Puerta Coralina @ Old Town - Cottage Near Duval

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** This precious 2 bedroom cottage with its coral front door will charm you from the moment you walk in the front gate. The front porch is private, for some quiet time reading a book. Inside, you'll see that PUERTA CORALINA reflects the simpler side of tropical living but with some useful updates.

Sep 27 – Oct 4

R11,974 ZAR per night

Guest favorite

Home in Cudjoe Key

4.97 out of 5 average rating, 124 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Sep 2 – 9

R5,555 ZAR per night

Guest favorite

Home in Marathon

4.99 out of 5 average rating, 107 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Apr 5 – 12

R15,302 ZAR per night

Guest favorite

Home in Marathon

4.97 out of 5 average rating, 33 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

You don't come to the islands to stay in a town! Relax in our tropical paradise beach home away from the traffic and noise of US Hwy #1. The perfect location has now been turned into the perfect oasis. Special features include a gourmet kitchen, private pool surrounded by lush landscaping, private 300' pier/dock with a fish cleaning station. Our guests enjoy luxury bedding with quality linens, fluffy towels and bathrobes. Wireless internet service and cable tv.

Apr 12 – 19

R11,465 ZAR per night

Superhost

Home in Cudjoe Key

4.81 out of 5 average rating, 222 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Dec 8 – 15

R7,632 ZAR per night

Superhost

Home in Cudjoe Key

4.89 out of 5 average rating, 194 reviews

Newly Renovated Oceanside House with Pool

This home is on the Atlantic side of US 1. It is part of Sunrise Beach Resort, a gated community built in 2007 with only 10 other homes. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, where you can soak up the sun steps from the house. Breathtaking southwest views of the blue-green ocean and sunsets can be seen from the pool and dock.

Sep 17 – 24

R6,575 ZAR per night

Guest favorite

Home in Marathon

5.0 out of 5 average rating, 7 reviews

Ocean Dream

Ocean Dream.... a bright beautiful upscale home with fantastic ocean views over Florida Bay. Watch sunsets and sunrises from either balcony. Experience nature at its finest from your 140 foot ocean frontage estate or go further afield on the included kayaks and SUPs. Beautiful gardens, outdoor living area, new pool and spa*, ping pong and bocce, all included in your week of paradise. License VACA 23-380

Nov 2 – 9

R16,426 ZAR per night

Superhost

Home in Sugarloaf Key

4.82 out of 5 average rating, 88 reviews

Palms Resort at Sugarloaf Beach - Guest House

One of a kind beach house with a private sandy beach, dock and boat dockage . Featuring a tropical ambiance and a family friendly setting that will make you feel like you are in your own private island. Gorgeous ocean views. natural Florida Keys private beach, great for swimming, snorkeling, kayaking, paddle boarding or just reading a book by a palm tree.

Oct 8 – 15

R19,211 ZAR per night