House holiday rentals in Sunset Key

4.99 out of 5 average rating, 133 reviews

Sea Ray Cove, Mini Lobster week NOW OPEN!

2025 - New concrete dock, fenders & fish filet table. 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.

4.95 out of 5 average rating, 38 reviews

Dock Pool Home by Sombrero Beach

This spectacular home is in the heart of Paradise. Sombrero beach just a few blocks away, Golfing across the street and your boat in our dock, everything you need to enjoy paradise! Situated in a very quiet and desirable neighborhood close to the beach and shopping. This home is a private oasis. The golf course is directly in front of the home. The home offers a private swimming pool with spa. There is 75' of deep water dockage which offers a straight shot out to the Ocean or Bootkey VACA-21-493

4.92 out of 5 average rating, 283 reviews

Home in Key West

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

The Historic Family House is decorated in a light, Caribbean motif. It is a Cigar Maker's Cottage from 1880's. 2 K memory foam beds upstairs w/32” Smart TV's, Q sleeper sofa (memory foam mattress) in LR with 56” Smart TV. Bring your Netflix, Amazon or other UN and PW for your favorite programming. Bose blue tooth speakers and Alexa's. 1/2 bath up, full bath down plus an outdoor private shower. Full kitchen! Perfect for Families! Private rear deck with new 6 person Jacuzzi. 2 heated pools!

4.94 out of 5 average rating, 47 reviews

Private Ocean Oasis by Key West, Florida

Beautiful stilted two bedroom/two bathroom vacation home awaits your arrival. Break taking views of the Atlantic Ocean are picture worthy. This home hosts a 36' seawall on a wide canal. Dock equipped with fishing cleaning station, cleats, swim ladder, outdoor shower and bait freezer. King-, queen-, full- and twin-size mattresses provide comfortable sleeping accommodations for all guests. Extensive indoor and outdoor furniture allow for all to relax, recharge and enjoy their time in paradise!!

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Home in Key West

5 out of 5 average rating, 7 reviews

Casa Calypso 3bed3bath sleeps 8 beautiful decorate

Bring the whole family to this great place with lots of room for fun. Very clean, organized stand alone house with everything you will need to have a great stay! Fully stocked kitchen with a kuerig and drip coffee pot. Can have twin beds downstairs or convert into a king. Two king bedrooms upstairs. Each bedroom has its own bath! A queen sleeper couch in living room with a screen divider for privacy if needed. Steps away from the large heated community pool. Several nice restaurants around.

4.83 out of 5 average rating, 30 reviews

Yellow Home Free Pontoon Rental! See details

If you book your stay for the days shown below May 10th - May 23rd, 2025 May 26th - June 7th, 2025 July 5th - July 26th, 2025 Receive a free 2 day boat rental for a week reservation, 1 day for a 3 days or more reservation. Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home nestled off of US 1. Kayaks included with the rental. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

Superhost

4.83 out of 5 average rating, 263 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!

4.9 out of 5 average rating, 105 reviews

*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.

4.9 out of 5 average rating, 232 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.

4.94 out of 5 average rating, 186 reviews

May availability 70ft Dock, Near Beach VACA23-16

Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.

4.94 out of 5 average rating, 33 reviews

Home in Summerland Key

Waterfront Captain House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin for your boat. The property lot is almost an acre with an island point surrounded by sea life. 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!

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