Key West Vacation Rentals, Beach Houses and Condo Rentals

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 vaulted ceiling, skylight, free WIFI, and digital HD cable........read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Apartment Rentals

Vacation Home

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 tours, and more. This 2 Bedroom, 2 Bath Condo sleeps 6, the primary suite has a king bed and connect.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

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 courtyards on the first level and balconies on the second level. Outdoor Grill. Each bedroom has on.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 4 Townhome Rentals

Vacation Home

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 center and two beautiful pools in an Old Town Key West setting. Tailgate Key is a spacious 1,320 sq.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals

Vacation Home

@Key West Morning Reflections Paradise Awaits April - Sep 2022@

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 for relaxing. The guest bedroom has a queen bed. High speed wireless internet. No attention to detai.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

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 bath and a great view of the ocean. From the second floor you can enjoy the fantastic view of the harb.......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals

Vacation Home

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 inhabit the salt ponds preserve that borders this property. .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

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 community, cameras all over public areas. General parking available. Kokomo is on 3rd floor with elev.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 5 Condo Rentals

Vacation Home

Ocean Front Key West Oasis. Tropical paradise awaits

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 for all to enjoy, famous for its literary experts, artists, theatre and museums. Many water activit.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

Fun in the Sun in the Truman Annex

This stately 2 bedroom townhouse in the President's Walk area of Porter Lane is furnished with tropical and luxury decor, and is loaded with amenities such as TV's in each bedroom. The 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 about ¼ mile from one of the best beaches on the island, Fort Zachary State Park. This Presid.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals

Vacation Home

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

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 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 open living plan and a beautiful private pool area that is ideal for relaxing in your own private oasi.......read more

3 Bedroom(s)
5 Bath(s) - Sleeps 8 House Rentals

Vacation Home

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 extra sleepers. Upstairs bedroom features a king-size bed, twin-size trundle bed & en-suite bath. Off .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

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

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 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 appears to be from the street. A dreamy open living plan, two spacious bedrooms, an office, an off-street.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 House Rentals

Vacation Home

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 entertaining overlooks the large rear yard with pool and is accessed from the living area through tw.......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals

Vacation Home

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

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 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 best of Old Town Key West. With your rental home at Sunset Marina you'll have plenty of space for par.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

Blue Lagoon in the Truman Annex

This cheery property located on Southard Street features three bedrooms, one on the first level and two on on the second. | There is a lovely kitchen, dining and living room which flows out through two sets of French doors onto the covered rear deck. | The private parking is very conveniently located in the rear and is covered. | There is a side bricked patio perfect for a quiet read, or a game of corn hole! There is an outdoor grill for those p.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Townhome Rentals

Vacation Home

Poolside Hangover @ the Truman Annex

This is an amazing two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy your time away from it all. Enjoy mornings out on the rear deck overlooking the refreshing community pool. Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and close to all of the Old Town Key West attractions. The properties are also located 1 mile from one of the best beaches on the i.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

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 the second level. All properties are outfitted with washer/dryer, pots & pans, towels & linens, hav.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

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 windows and natural light and ultra comfortable seating, lounging and dining areas on the first flo.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals

Vacation Home

**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 to offer. Yet, EDEN @ THE ANNEX is on a quiet pedestrian lane where you'll have all of the peace and .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 5 Townhome Rentals

Vacation Home

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 Sunshine State experience for a family or romantic couples retreat. The two-story townhouse was recentl.......read more

2 Bedroom(s)
2 Bath(s) House Rentals

Vacation Home

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 Outer Mole pier which is adjacent to the beautiful Truman Waterfront Park... This community is loca.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 5 Condo Rentals

Vacation Home

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 is located in the beautiful community of Truman Annex. This gated community offers the security and t.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals

Vacation Home

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 one vehicle. | Enjoy both the front and back rear deck has outdoor dining and lounging all year lon.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

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 includes a carport and a convenient community pool. | The President's Walk area of the Truman Annex is loca.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals

Vacation Home