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From $999 per night (USD)
VRBO
**THE BEAMING BARRACUDA @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERV
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE BEAMING B ...
From $999 per night (USD)
VRBO
From $662 per night (USD)
Expedia
Hyatt Beach House! Quiet Key West Location! Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located on a private beach, this quiet piece of Key West is an excellent choice for relaxation while also situated only ...
From $662 per night (USD)
Expedia
From $650 per night (USD)
VRBO
Sunset Harbor - Old Town Key West Location - Beautiful Property
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located ...
From $650 per night (USD)
VRBO
From $394 per night (USD)
VRBO
The Galleon Resort Best Resort Location in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has ...
From $394 per night (USD)
VRBO
Click For Pricing
VRBO
Studio at Hyatt Residence Club Key West, Sunset Harbor.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Seth Nock Licensed Broker, Selling Timeshares INC. Studio at Hyatt Residence Club Key West, Sunset Harbor. Check-in: ...
Click For Pricing
VRBO
From $304 per night (USD)
Expedia
Anchors Away - Old Town Key West
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Anchors Away offers traditional Conch style living and is located in the coveted Old Town Key West. This home is unbeata ...
From $304 per night (USD)
Expedia
From $338 per night (USD)
VRBO
TAILGATE KEY at the Key West Golf Club
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to Tailgate Key! This unique vacation property is located in the Key West Golf Club Community set amongst lush t ...
From $338 per night (USD)
VRBO
From $542 per night (USD)
Expedia
SWEET'S SPOT at The Truman Annex in Key West
Bedrooms:
5
Bathrooms:
3
Sleeps:
6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breathtaking water a ...
From $542 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Red Room at Grand Maloney Hotel with Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $367 per night (USD)
VRBO
From $381 per night (USD)
Expedia
BEST TIME at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This newly renovated shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautif ...
From $381 per night (USD)
Expedia
From $472 per night (USD)
VRBO
**ISLAND OPULENCE @ MIDTOWN** Grand Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
4
Sleeps:
11
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The moment yo ...
From $472 per night (USD)
VRBO
From $494 per night (USD)
Expedia
Harbor Walk Hideaways - African Queen Suite | Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: African Queen Cottage is part of the quiet complex called "Harbor Walk Hideaways," located in the Historic Seap ...
From $494 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Harbor Walk Hideaways - The Pilar's Cottage | Downtown with Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Pilar Cottage is part of the quiet complex called "Harbor Walk Hideaways," located in the Historic Seaport dist ...
From $436 per night (USD)
VRBO
From $2838 per night (USD)
Expedia
Harbor Walk Hideaways - Full Compound|Downtown with Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Summary: Harborwalk Hideaways is a stunning, newly-renovated vacation rental complex tucked away in the Historic Seaport ...
From $2838 per night (USD)
Expedia
From $485 per night (USD)
VRBO
POOLSIDE HANGOVER at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This is an amazing two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy your time away ...
From $485 per night (USD)
VRBO
From $1586 per night (USD)
Expedia
A Place on Emma at the Truman Annex in Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Beautifully renovated & furnished 4 bedroom/ 4 bath single family home including a charming detached guest cottage is lo ...
From $1586 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Beautiful Marina location. Gated community. Quite and secure. SUNSETS !!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunset Marina Condominium Complex is a gated community that has a community pool and spa, and clubhouse. All of the two ...
From $208 per night (USD)
VRBO
From $380 per night (USD)
Expedia
A DUCK ON THE GREEN at the Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
A Duck on the Green --This lovely, fully furnished, townhouse has two and a half bedrooms that sleeps up to five and two ...
From $380 per night (USD)
Expedia
From $392 per night (USD)
VRBO
SOUTHERNMOST SANCTUARY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Southernmost Sanctuary is a beautiful two bedroom, one bath condominium has recently been updated located in the Shipyar ...
From $392 per night (USD)
VRBO
From $455 per night (USD)
Expedia
Road's End | Steps to Duval St!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Just a stone's throw away from Mile Marker Zero lies the aptly named "Road's End," a charming 1 Bd, 1.5 Bth tow ...
From $455 per night (USD)
Expedia
From $387 per night (USD)
VRBO
Come escape to Island Time Hideaway - Wonderful monthly renovated rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Beautifully renovated 2 bedroom 2 bath condo at the exclusive 1800 Atlantic Condo's. Each bedroom has a king size bed an ...
From $387 per night (USD)
VRBO
$Shipyard 276-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w\/ pool$
From $413 per night (USD)
Expedia
Shipyard 276-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w\/ pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $413 per night (USD)
Expedia
$Captain's Daughter: Oversized home for the whole family w\/private pool & dock$
From $1860 per night (USD)
VRBO
Captain's Daughter: Oversized home for the whole family w\/private pool & dock
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $1860 per night (USD)
VRBO
From $486 per night (USD)
Expedia
HIGH TIDE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
If you have high expectations, you are going to enjoy staying at High Tide. You are within walking distance to restaura ...
From $486 per night (USD)
Expedia
From $552 per night (USD)
VRBO
A CONCH ESCAPE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Location, location, adorable two bedroom, one bath second floor condo overlooking the Truman Waterfront Park is the per ...
From $552 per night (USD)
VRBO
From $423 per night (USD)
Expedia
A SUNSET VIEW at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $423 per night (USD)
Expedia
From $1130 per night (USD)
VRBO
Spacious home with pool & balcony - 1 block from Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Last Minute Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $1130 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Charming home in Old Town, walk to shops & restaurants - yard
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Gingerbread Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $234 per night (USD)
Expedia
From $388 per night (USD)
VRBO
GYPSY'S PALACE in the Truman Annex - Stunning ocean views!!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Fabulous waterfront two level condo in the beautiful Historic Mills Place Hospital Building in the Truman Annex awaits! ...
From $388 per night (USD)
VRBO
From $482 per night (USD)
Expedia
ARCHIPELAGO l at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $482 per night (USD)
Expedia
From $291 per night (USD)
VRBO
Old Town Charm Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming Old Town cottage is a short walk to Duval Street nightlife, restaurants, shops and culture… and a walk or ...
From $291 per night (USD)
VRBO
From $449 per night (USD)
Expedia
Location, Beauty & Comfort @ Truman Annex
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $449 per night (USD)
Expedia
From $934 per night (USD)
VRBO
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Like many hig ...
From $934 per night (USD)
VRBO
From $1049 per night (USD)
Expedia
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
4 Bedroom, 3 Bathroom, Sleeps 8 Luxurious furnishings and spacious interiors centered around the expansive water views p ...
From $1049 per night (USD)
Expedia
$Alluring corner unit w\/ full kitchen & pool - close to beach\/ nightlife$
From $629 per night (USD)
VRBO
Alluring corner unit w\/ full kitchen & pool - close to beach\/ nightlife
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Seaclusion Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $629 per night (USD)
VRBO
$Wonderful Condo in Key West w\/Free WiFi, Lanai, A\/C, Shared Hot Tub & Pool$
From $345 per night (USD)
Expedia
Wonderful Condo in Key West w\/Free WiFi, Lanai, A\/C, Shared Hot Tub & Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Tradewinds at Smathers Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $345 per night (USD)
Expedia
From $478 per night (USD)
VRBO
Sky Loft, Downtown | Penthouse in Prime Spot!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: This gem of a top floor apartment is perfect for your weekend getaway. Sky Loft is located just one block away ...
From $478 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Claude Monet Suite | Pool & Patio
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Micro-efficiency near downtown Key West! The Galleria was once a haven for traveling artists who frequented K ...
From $336 per night (USD)
Expedia
From $973 per night (USD)
VRBO
BLUE LAGOON at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This cheery property located on Southard Street features three bedrooms, one on the first level and two on on the second ...
From $973 per night (USD)
VRBO
$**SUGARPOPPY COTTAGE** Cozy Cottage \/ Private Pool + LAST KEY SERVICES$
From $349 per night (USD)
Expedia
**SUGARPOPPY COTTAGE** Cozy Cottage \/ Private Pool + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Look for the ...
From $349 per night (USD)
Expedia
From $3908 per night (USD)
VRBO
Takeover at the Grand Maloney by Brightwild
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $3908 per night (USD)
VRBO
From $2044 per night (USD)
Expedia
**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Get the gang ...
From $2044 per night (USD)
Expedia
From $243 per night (USD)
VRBO
Sailor's Sanctuary - A Renovated Condo in Old Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Renovated ground floor apartment in Truman Annex. Steps from Duval Street! Enjoy all that the beautiful gated community ...
From $243 per night (USD)
VRBO
From $745 per night (USD)
Expedia
Hidden Beach - the perfect place to stay in Key West
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Hidden Beach Unit 3 - In Old Town, just 3 blocks from Duval Street; this property sits on Key West’s only natural beach. ...
From $745 per night (USD)
Expedia
From $1948 per night (USD)
VRBO
Historic Old Town Key West - Main House, Sleeps 8
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
OVERVIEW The 'Main House' is a two-story, four (4) bedroom, one and a half (1.5) bathroom renovated historic home. The ...
From $1948 per night (USD)
VRBO
From $2186 per night (USD)
Expedia
Features.Key West Suites Hotel has an outdoor pool and fitness center
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used ...
From $2186 per night (USD)
Expedia
From $923 per night (USD)
VRBO
ARCHIPELAGO in the Truman Annex
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
This gorgeous townhouse has 4 bedrooms, 4 full Bathrooms, and 2 half bathrooms. It is unique in that it has 2 of everyt ...
From $923 per night (USD)
VRBO
From $731 per night (USD)
Expedia
SUNSET DALITE at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Enjoy the breathtaking views of the Atlantic Ocean and the Gulf of Mexico from your front row seat! | This gorgeous cond ...
From $731 per night (USD)
Expedia
From $720 per night (USD)
VRBO
AQUA BREEZE at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...
From $720 per night (USD)
VRBO
From $609 per night (USD)
Expedia
Hidden Beach Unit 1. The perfect place to stay in Key West for less
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Hidden Beach Unit 1 - Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach ...
From $609 per night (USD)
Expedia
From $420 per night (USD)
VRBO
SHADY NOOK at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Two blocks away from Duval Street with direct access to Thomas Street through the rear gate. Has free hook up for intern ...
From $420 per night (USD)
VRBO
From $280 per night (USD)
Expedia
A PALM TREE PARADISE @ the Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A Palm tree Paradise***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***Stay on the only 18-hole golf club in the Florida Key ...
From $280 per night (USD)
Expedia
From $526 per night (USD)
VRBO
ROYAL POINCIENA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $526 per night (USD)
VRBO
From $859 per night (USD)
Expedia
THE PLANTATION in the Truman Annex
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
‘The Plantation” is a Three Bedroom Town home located within the prestigious gated community of ‘Truman Annex’ in Key We ...
From $859 per night (USD)
Expedia
From $1006 per night (USD)
VRBO
A GULFSTREAM DRIFT at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This tropical retreat in Paradise h ...
From $1006 per night (USD)
VRBO
From $548 per night (USD)
Expedia
LIFE IN THE SLOW LANE at the Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
This charming unit has a whimsical nautical feel with the blue and white décor. There are two master suites, one on t ...
From $548 per night (USD)
Expedia
From $864 per night (USD)
VRBO
SALTWATER ANGLER at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating includin ...
From $864 per night (USD)
VRBO
From $392 per night (USD)
Expedia
Island Breezes at The Truman Annex in Key West@ the Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming second floor condominium features two bedrooms, and one full bath with views of the Truman Waterfront Park ...
From $392 per night (USD)
Expedia
From $897 per night (USD)
VRBO
A HARBOUR ROOST at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $897 per night (USD)
VRBO
From $513 per night (USD)
Expedia
A SANCTUARY HOME at the Key West Golf Club
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
A Sanctuary Home*****PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***** | Stay on the only 18-hole golf club in the Florida ...
From $513 per night (USD)
Expedia
From $499 per night (USD)
VRBO
BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This beautiful gated home is located on an oversized corner lot a few blocks from White Street Pier and Higg's Beach wit ...
From $499 per night (USD)
VRBO
From $502 per night (USD)
Expedia
ASCENSION at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stepping through the white picket gate into this town home located in the gated Truman Annex community, in the heart of ...
From $502 per night (USD)
Expedia
From $462 per night (USD)
VRBO
DANCING PALMS at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come stay at this bright and airy 2 bedroom, 2 full bath town home in the renowned Truman Annex in Old Town. Leave the c ...
From $462 per night (USD)
VRBO
From $639 per night (USD)
Expedia
Oceanfront Hidden Beach Unit 2 - The best place to stay in Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlan ...
From $639 per night (USD)
Expedia
From $854 per night (USD)
VRBO
OCEAN BREEZE at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Gorgeous open water views from this 2-bedroom, 2.5 bath condominium in Harbour Place in the award-winning Truman Annex! ...
From $854 per night (USD)
VRBO
From $588 per night (USD)
Expedia
SAGO PALM at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $588 per night (USD)
Expedia
From $350 per night (USD)
VRBO
The Bolivar, Old Town Key West Monthly vacation rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tuck upstairs in the back of a historic Conch house is a home away from home with private back porch. 1 Block walk from ...
From $350 per night (USD)
VRBO
From $722 per night (USD)
Expedia
~ SOLARIS PAIR-A-DISE ~ A garden lover’s dream on a quiet Key West lane.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE PROPERTY: If you are looking for that tropical island vibe, look no further! Both sections of this casual home are ...
From $722 per night (USD)
Expedia
From $455 per night (USD)
VRBO
The Patricia, 1 BR, 1 BA monthly vacation rental home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in the heart of Old Town Key West is a quaint Key West Home that offers a crisp palette of blue, lime and white ...
From $455 per night (USD)
VRBO
From $501 per night (USD)
Expedia
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for compute ...
From $501 per night (USD)
Expedia
From $520 per night (USD)
VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
We love this home, and we just know you will too!! A fully renovated conch home with amazing finishes and 3 great bedro ...
From $520 per night (USD)
VRBO
From $1377 per night (USD)
Expedia
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Don't miss an ...
From $1377 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Garden of Roses | Pvt Hot Tub, Amazing Location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Feel like a local and immerse yourself in all Key West has to offer when you stay at Garden of Roses! This epic ...
From $314 per night (USD)
VRBO
$CEASAR'S PARADISE - A MODERN LUXURY RETREAT W\/ 4+ Bedrooms\/ 5.5 Baths$
From $777 per night (USD)
VRBO
CEASAR'S PARADISE - A MODERN LUXURY RETREAT W\/ 4+ Bedrooms\/ 5.5 Baths
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Modern sophistication is the design aesthetic in this newer built home in Old Town Key West with designer touches throug ...
From $777 per night (USD)
VRBO
From $567 per night (USD)
VRBO
Two Bedroom Two Bath Balcony Villa Steps from Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Two Bedroom Balcony Villa is a gracious two story Key West rental decorated in a tropical style with a living room, ...
From $567 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
We want you to know that your safety and comfort while in Key West is our utmost priority. Cleaning supplies are availab ...
From $474 per night (USD)
Expedia
$VILLA BELLA - AN EXCEPTIONAL 5\/4 ISLAND HOME-Convenient to Old Town$
From $930 per night (USD)
VRBO
VILLA BELLA - AN EXCEPTIONAL 5\/4 ISLAND HOME-Convenient to Old Town
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
28 Night Minimum Stay Required. This beautiful island retreat is secluded away on a quiet Old Town lane and features 5 l ...
From $930 per night (USD)
VRBO
$TUCKED AWAY OFF DUVAL - A contemporary home w\/ local color at your door step$
From $508 per night (USD)
VRBO
TUCKED AWAY OFF DUVAL - A contemporary home w\/ local color at your door step
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Location, location, location! Tucked Away is set on a small lane just one block from Duval Street, 2 blocks to the Hemin ...
From $508 per night (USD)
VRBO
From $632 per night (USD)
VRBO
The Salt Cay | Sunset Views, Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $632 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nice quiet vacation landing a few blocks from the action on Duval Street. This Saturday-Saturday home in Key West has: - ...
From $307 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Prime location, stunning views from 2 decks—walk or ride to explore the island!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Walk everywhere from this little part of Paradise, you will never need a car. Located in beautiful Old Town, you are vi ...
From $436 per night (USD)
VRBO
From $567 per night (USD)
Expedia
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We have the perfect accommodation for a family vacation or friends getaway in Old Town Key West, Florida. Our Two-Bedroo ...
From $567 per night (USD)
Expedia
From $1221 per night (USD)
VRBO
Sailor's Son: Waterfront 4 Bedroom 4 bath Luxury Home in Key Cove Landings
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1221 per night (USD)
VRBO
$GOLF VILLA - Monthly Rental - 2BD\/2BA -Community Pool - RealKeyWest$
From $241 per night (USD)
Expedia
GOLF VILLA - Monthly Rental - 2BD\/2BA -Community Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Golf Villa, your perfect Key West getaway in the highly sought-after Key West Golf Club neighborhood! Immerse ...
From $241 per night (USD)
Expedia
From $427 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 1
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The unit located on the first floor has three-dimensional ceilings throughout with indirect LED lighting. The kitchen is ...
From $427 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Sea Breeze at 1800 Atlantic
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New Listing January 2022! Sea Breeze at 1800 Atlantic is a two bedroom / two bathroom fully furnished condo located in ...
From $304 per night (USD)
Expedia
From $553 per night (USD)
VRBO
St. Martin Suite | Beautifully Updated, Pool View
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: - Welcome to the tropical & relaxing Sunrise Suites Resort, located on the quiet side of Key West! - Just 1 mil ...
From $553 per night (USD)
VRBO
From $567 per night (USD)
Expedia
Pool View & Walk To Beach | The Grand Cayman
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $567 per night (USD)
Expedia
From $1032 per night (USD)
VRBO
1 BLOCK OFF DUVAL! PRIVATE POOL AND HOT TUB
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Enjoy one of Old Town's wonderful historic homes with private pool and hot tub. Casa Rosa one of only seventy five remai ...
From $1032 per night (USD)
VRBO
From $484 per night (USD)
Expedia
BEACHFRONT-Coconut Beach Resort, 7 nights, May 10-17, or May 31-June 7, only.
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Private tropical Paradise on the Atlantic Ocean in Key West, Florida. This condo unit is a 1 bedroom, with 2 full bathro ...
From $484 per night (USD)
Expedia
From $338 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-mi ...
From $338 per night (USD)
VRBO
$Ocean Front & Ocean View. Across from Smathers beach. Sleeps 6, 2\/2 baths.$
From $457 per night (USD)
VRBO
Ocean Front & Ocean View. Across from Smathers beach. Sleeps 6, 2\/2 baths.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
"Kokomo" is what we have named our unit. It is a 2 bedroom 2 baths with queen sleeper sofa in living room . We sleep 6 g ...
From $457 per night (USD)
VRBO
From $1086 per night (USD)
VRBO
Get Ready for Your Florida Adventure! Nightlife, Bike Rentals, 3 Pools, Spa!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1086 per night (USD)
VRBO
From $846 per night (USD)
VRBO
Your Exciting Florida Vacay Starts Here! Nightlife, Island View, Restaurant!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $846 per night (USD)
VRBO
From $1016 per night (USD)
VRBO
Your Key West Adventure Awaits! Ocean View, Pool, Outdoor Dining, Nightlife!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1016 per night (USD)
VRBO
From $769 per night (USD)
VRBO
Beachside Dream! Steps to Sand, Pool, Beach Bar, Nightlife! Near Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $769 per night (USD)
VRBO
From $695 per night (USD)
VRBO
La Mer Dewey Island View Accommodation at Southernmost Beach Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $695 per night (USD)
VRBO
From $903 per night (USD)
VRBO
Tropical Key West Getaway! Enjoy Island View from your Room, Swimming Pools!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $903 per night (USD)
VRBO
From $1538 per night (USD)
VRBO
2 x Partial Ocean View Balcony 2 Queen Beds Rooms at Southernmost Beach Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1538 per night (USD)
VRBO
From $848 per night (USD)
VRBO
Steps From The Sand! Ocean Views, 3 Pools, Onsite Dining, Bike Rental, Nightlife
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $848 per night (USD)
VRBO

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