Skip to content
Home » Vacation Rentals » Key West

Key West Vacation Rentals, Beach Houses and Short Term Rental Homes by Owner

Book Your Key West, Florida Keys Florida Vacation Rental Homes Here and Save! Many to choose from!

Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Key West, Florida Keys, Florida.

We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals in Key West, Florida Keys to choose from, we now have the selection and value to offer our visitors going to Florida.

Listings

Vacation Rental

Suite Blu - A monthly rental apartment in a great location

Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West. This monthly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided. This property will meet all of the demands a vacationer might have. Other amenities include a vaul.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Key West Apartment Rental

Details


Vacation Rental

Sunset Harbor - Old Town Key West Location - Beautiful Property

Welcome to the perfect location in old town Key West. Situated on the western side of the island, this property overlooks the Gulf of Mexico. Outside the property enjoy the charms of Duval Street and a nightly sunset celebration at Mallory Square. There are also many activities like diving, scuba or snorkeling, parasailing, fishing charters, boat t.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Key West Condo Rental

Details


Vacation Rental

SAGO PALM in the Truman Annex

The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located less than a half mile from one of the best beaches on the island. The Presidents Walk properties are two level townhouses which have private.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 4 Key West Townhome Rental

Details


Vacation Rental

TAILGATE KEY at the Key West Golf Club

Welcome to Tailgate Key! This unique vacation property is located in the Key West Golf Club Community set amongst lush tropical landscaping, beautiful greens and fairways of the Rees Jones designed 18-hole course. There are gorgeous views of the lake and golf course from the furnished screened outdoor deck. This gated community includes a fitness.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 6 Key West Townhome Rental

Details


Vacation Rental

Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun. KWF

Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious walk in shower. King size bed with a flat screen TV .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Key West Condo Rental

Details


Vacation Rental

DOLPHIN WATCH @ the Truman Annex

VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attractions and the famous Fort Zachary Taylor Beach. This home has 2 master ensuites with king beds, and there is a total of 4 bedrooms and 3 baths. The second level offers open living and kitchen area, master bedroom with ensuite bat.......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 8 Key West House Rental

Details


Vacation Rental

Quiet, elegant, Key West Condo close to the Ocean

This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located one mile from Smathers Beach, two miles from Higgs Beach and just minutes away from the Key West Lighthouse Museum. Many species of birds inh.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Key West Condo Rental

Details


Vacation Rental

Ocean Front with Ocean View. Across from Smathers beach. Sleeps 5, 2/2 baths.

"Kokomo" is what we have named our unit. It is a 2 bedroom 2 baths with queen sleeper sofa in living room . We sleep 5 guests only. Central AC in unit, clean unit, living/dinning is open concept. Master bedroom with a king bed, with private bathroom and access to balcony. W/D in unit, full kitchen, beach towels, Reg. towels. 3 TV's, Wi-Fi. Gated co.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 5 Key West Condo Rental

Details


Vacation Rental

Ocean Front Key West Oasis. Island Tones, Charming Historical Downtown area.

Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size washer dryer. Enjoy all the comforts of home with a fab Key West is a playground.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Key West Condo Rental

Details


Vacation Rental

**VIVA MARGARITA! @ OLD TOWN** Large Home & Pool Near Duval + LAST KEY SERVICES.

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is the mecca for those seeking to live life the way it is supposed to be lived: in the sunshine with a cold drink in hand. "Viva Margarita!" was designed to house those sun-seekers. This tropically decorated three-story home has an op.......read more

3 Bedroom(s)
5 Bath(s) - Sleeps 8 Key West House Rental

Details


Vacation Rental

The Key West Bougain Villa, a Monthly Vacation Rental

The Bougain Villa is found on Whitehead Street. Reserve a stay in this home located in the heart of historic Old Town Key West. This 2 bedroom and 2 bathroom house features plenty of space to accommodate guests comfortably. First-floor bedroom includes a queen-size bed & en-suite bath. Additionally, the living room sofa pulls out into a bed for ex.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Key West House Rental

Details


Vacation Rental

**MARA-VILLA @ OLD TOWN** Private Conch Home & Hot Tub + LAST KEY SERVICES...

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! MARA-VILLA is a quintessential Key West cottage that has been beautifully maintained and cared for to welcome the most discerning Key West lovers for a month in paradise. This lovingly designed conch home is exactly the Key West gem it appear.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Key West House Rental

Details


Vacation Rental

QUEEN EMMA in the Truman Annex

This beautifully finished and decorated four bedroom, three bath home has classic Key West architecture and is located on a charming tree lined street in Truman Annex. The custom designed two story home has an open floor plan on the main level with separate living and dining areas. Plus a full bath and guest bedroom. | The huge porch, perfect for .......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 8 Key West House Rental

Details


Vacation Rental

**SUNSET REVERIE @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SUNSET REVERIE is located in Sunset Marina, a gated community located on Stock Island right off the entrance to Key West. The location is a great balance between being secluded in a private community yet still only a short Uber ride into the b.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Key West Condo Rental

Details


Vacation Rental

STARSHINE KEY WEST in the Truman Annex

Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located 1/4 mile from one of the best beaches on the island. The Shipyard units are single level condominiums which have private courtyards on the first level or balconies on.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Key West Condo Rental

Details


Vacation Rental

VILLA AZURA THE BEST place to be in Key West!

Welcome to Villa Azura - this is Enjoy this gem on a quiet lane in the award-winning gated community of the Truman Annex. Recently transformed, this beauty features a brand new kitchen with Viking appliances, gas stove, gorgeous cabinetry, wine cooler and an inviting kitchen top bar. Sink into the sweeping floorplan with tall ceilings, plenty of.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 6 Key West House Rental

Details


Vacation Rental

**EDEN @ THE ANNEX** Old Town Villa & Pool by Duval + LAST KEY SERVICES...

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to your arrival! EDEN @ THE ANNEX is a charming townhome in Truman Annex, a gated community located in the very heart of Old Town Key West. You'll be just steps from Mallory Square, Duval Street and all the attractions Key West has t.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 5 Key West Townhome Rental

Details


Vacation Rental

Presidents Walk, 2BDR, 1.5BA Townhouse with shared pool at Truman Annex

~~7 DAY MINIMUM~~​Experience the famous island city of Key West and stay at the Presidents Walk Townhouse in the private President's Lane area of the prestigious Truman Annex.  Offering exquisite amenities, pool access, and an unbeatable location close to Duval Street, Truman Waterfront Park, and Ft. Zachary Taylor Beach provides a fantastic Sun.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Key West House Rental

Details


Vacation Rental

WORLDS END in the Truman Annex

This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water and sunset views from the large and luxurious pool area and large terraces. This beautifully decorated two bedroom, two and a half bath stately condo has wonderful views of the Atlantic Ocean and Sunset Key along the length of the.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 5 Key West Condo Rental

Details


Vacation Rental

LATITUDE ADJUSTMENT at the Truman Annex

This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renovated to accommodate an individual couple, family, or vacationing couples that each desires the privacy of their own bedroom suite with full, private baths. This two bedroom, two and one half unit will comfortably sleep up to six i.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 6 Key West Townhome Rental

Details


Vacation Rental

A LOW TIDE in Truman Annex

A Low Tide is a charming first floor end unit in the Shipyard Condominiums in the award wining gated community of the Truman Annex. | This property has recently been refreshed featuring new appliances, tvs, bedding, etc.! | It is is located 2 blocks from Duval Street and all of the Old Town Key West attractions and includes off street parking for o.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Key West Condo Rental

Details


Vacation Rental

CAPTAINS WHEEL in the Truman Annex

This very popular getaway in the award-winning Truman Annex is a tropically decorated 2 bedroom, 2.5 bath town home featuring an open floor plan with a great rear deck for entertaining and relaxing. The master bedroom has it's own balcony and the guest bedroom features a covered porch offering plenty of outdoor living. This opportunity also include.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 6 Key West Townhome Rental

Details


Vacation Rental

SUN, SEA, AND SKY in the Truman Annex

Sun Sea and Sky is only two blocks from bustling Duval Street, the heart of Old Town Key West, with an easy walk to restaurants, shops and many other Key West attractions. Sun, Sea & Sky, decorated with private art and lots of mirrored walls, boasts a large rear deck with a 50% overhang to protect you from the elements while enjoying the shade of l.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Key West Condo Rental

Details


Gallery

Discover the Best Deals for Key West Vacation Rentals in the Florida Keys.

We have 2,3 or 4 Bedroom beachfront Vacation Rental Homes with ocean view or a Beach House for the entire family. Book Direct Here!

Key West, FL is known for watersports, lively nightlife, beaches, historic sites and its pastel, conch-style architecture. Located at the southernmost point in the Florida Keys and the United States, visitors can enjoy the Ernest Hemingway Home and Museum, tour the Harry S. Truman Little White House, explore beautiful tropical gardens or visit Mallory Square, a waterfront plaza just west of Duval Street where its “Sunset Celebration” is one of the most popular things to see and do in Key West.

Scroll To Top