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From $430 per night (USD)
VRBO
Heart of Old Town; 2 Bicycles, Grill, High Speed WiFi, 1st Floor, Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Our condo has always ...
From $430 per night (USD)
VRBO
From $342 per night (USD)
Expedia
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $342 per night (USD)
Expedia
$~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool\/parking$
From $3409 per night (USD)
VRBO
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool\/parking
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a priv ...
From $3409 per night (USD)
VRBO
$Henry's Penthouse on the Ocean in Key West - weekly \/ nightly rentals$
From $573 per night (USD)
Expedia
Henry's Penthouse on the Ocean in Key West - weekly \/ nightly rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft pr ...
From $573 per night (USD)
Expedia
$**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR\/2BA Condo & Pool + LAST KEY SERVICE$
From $978 per night (USD)
VRBO
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR\/2BA Condo & Pool + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OLD TOWN OASI ...
From $978 per night (USD)
VRBO
$Comfortable Home with Private Pool, Central AC, WiFi, and Private Washer\/Dryer$
From $533 per night (USD)
Expedia
Comfortable Home with Private Pool, Central AC, WiFi, and Private Washer\/Dryer
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Flagler Station Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $533 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $390 per night (USD)
VRBO
From $508 per night (USD)
Expedia
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $508 per night (USD)
Expedia
From $329 per night (USD)
VRBO
COCONUT Adorable cottage in Old Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The 'Coconut' as it's so lovingly referred to is the perfect Pied A Terre for your vacation in the Florida Keys. Open l ...
From $329 per night (USD)
VRBO
From $839 per night (USD)
Expedia
**COASTLINE COMFORT @ COCONUT MALLORY** Condo + 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! When your vac ...
From $839 per night (USD)
Expedia
From $701 per night (USD)
VRBO
**SET SAIL @ COCONUT MALLORY** Condo + 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! SET SAIL cele ...
From $701 per night (USD)
VRBO
From $231 per night (USD)
Expedia
Cozy studio cottage in Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to ...
From $231 per night (USD)
Expedia
From $1018 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Minimum Age: 25 years old Pet Policy: No Pets An ID and credit card for a refundable security deposit will be required. ...
From $1018 per night (USD)
VRBO
Click For Pricing
Expedia
Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
WELCOME TO LITTLE CASITA! If looking for the perfect couple’s retreat, look no further! This one bedroom, one bath hi ...
Click For Pricing
Expedia
From $781 per night (USD)
VRBO
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! While Old Tow ...
From $781 per night (USD)
VRBO
From $901 per night (USD)
VRBO
Amazing Stay, Great Location! Bike Rental, Pools, Onsite Bar
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $901 per night (USD)
VRBO
From $459 per night (USD)
VRBO
Luxurious Vacation! Pools, Tiki Bar, Bike Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $459 per night (USD)
VRBO
From $161 per night (USD)
Expedia
Ground-level getaway with free WiFi, private deck, & shared outdoor pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Louisa's Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $161 per night (USD)
Expedia
$Hyatt Windward Pointe, Key West, Fl. - 2 Bedroom Unit - 1064 sq\/ft$
Click For Pricing
Expedia
Hyatt Windward Pointe, Key West, Fl. - 2 Bedroom Unit - 1064 sq\/ft
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
3rd floor (top level accessible by elevator or stairs) Balcony faces the Atlantic Ocean and gardens. 2 bedrooms (large m ...
Click For Pricing
Expedia
From $483 per night (USD)
Expedia
SOUTHERNMOST SWIM AND SOCIAL CLUB
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Look no further! You've found your home away from home. Where your family and friends can share their own piece of para ...
From $483 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Welcome to the Shady Palms - Private Pool - RealKeyWest
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $369 per night (USD)
VRBO
$Treasure Cove- 2BDR\/2.5BA | 2 Bed, 2.5 Bath$
From $645 per night (USD)
Expedia
Treasure Cove- 2BDR\/2.5BA | 2 Bed, 2.5 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
~~7 day minimum~~Experience the famous island city of Key West and stay at the Treasure Cove Townhouse in the private P ...
From $645 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Quiet Lane in the Heart of Old Town, Sleeps 4 + 🐶🐾
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unbeatable location just 1 block from the iconic Green Parrot Bar and 2 blocks from world famous Duval Street. Blue Heav ...
From $416 per night (USD)
VRBO
$ISLAND TIME - 5 Bed\/3 Bath OldTown Complex - MONTHLY - Private pool$
From $941 per night (USD)
Expedia
ISLAND TIME - 5 Bed\/3 Bath OldTown Complex - MONTHLY - Private pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
WELCOME TO ISLAND TIME! Key West Island Time is a rare find in old town Key West. It is a total of 5 bedrooms and three ...
From $941 per night (USD)
Expedia
$Tropical Jewel: Historic Seaport Oldtown - 2BR\/2BA - Pool - RealKeyWest$
From $286 per night (USD)
VRBO
Tropical Jewel: Historic Seaport Oldtown - 2BR\/2BA - Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
WELCOME TO TROPICAL JEWEL! Near all the action of the historic seaport and Duval Street, you can get out into the cit ...
From $286 per night (USD)
VRBO
From $585 per night (USD)
Expedia
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $585 per night (USD)
Expedia
From $493 per night (USD)
VRBO
MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Featured in The Key West Citizen Home of the Week. Perfect location, and newly renovated with fresh paint, new kitchen w ...
From $493 per night (USD)
VRBO
From $1754 per night (USD)
Expedia
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Hidden amongs ...
From $1754 per night (USD)
Expedia
$Getaway in Key West: Tranquil Room w\/ Balcony | Resort w\/ Pool Access$
From $783 per night (USD)
VRBO
Getaway in Key West: Tranquil Room w\/ Balcony | Resort w\/ Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $783 per night (USD)
VRBO
$Old Town Key West Family Retreat | Spacious Room w\/ Balcony | Parking Onsite$
From $851 per night (USD)
VRBO
Old Town Key West Family Retreat | Spacious Room w\/ Balcony | Parking Onsite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $851 per night (USD)
VRBO
From $767 per night (USD)
VRBO
ADMIRAL'S PARADISE in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ...
From $767 per night (USD)
VRBO
From $1435 per night (USD)
Expedia
Sky Suites Retreat, On Duval –2 Stunning Condos
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Summary: This elegant, elevated 2nd story loft with vaulted ceilings has been designed for your next dream Key West geta ...
From $1435 per night (USD)
Expedia
From $453 per night (USD)
VRBO
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situa ...
From $453 per night (USD)
VRBO
From $858 per night (USD)
VRBO
Key West's Crown Jewel
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Key West's Crown Jewel is a penthouse condominium at 1800 Atlantic Condominium development with two-bedroom, two-bath wi ...
From $858 per night (USD)
VRBO
From $692 per night (USD)
VRBO
Tortuga Suite | Sparkling Pool & Hot Tub!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: - Welcome to the quiet & relaxing Sunrise Suites community located on the southeast side of Key West. - Just 1 ...
From $692 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful & Relaxing 2 bed 2 bath condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a large 2 bed 2 bath condo with a separate living room, kitchen, and private balcony at the Hyatt Resort. It off ...
Click For Pricing
Expedia
From $817 per night (USD)
VRBO
Southernmost Retreat: 2 Blocks from Duval in Old Town.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated a ...
From $817 per night (USD)
VRBO
From $401 per night (USD)
Expedia
Casa Verde - Perfection in a monthly rental - private pool - RealKeyWest
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
The moment you walk thru the door you are greeted by soothing tropical colors and high vaulted ceilings. The large mast ...
From $401 per night (USD)
Expedia
From $521 per night (USD)
VRBO
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! It is not so ...
From $521 per night (USD)
VRBO
From $577 per night (USD)
Expedia
**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! If you’re loo ...
From $577 per night (USD)
Expedia
From $379 per night (USD)
VRBO
Flirty Flamingo Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Flirty Flamingo is luxurious and in a prime Key West location. Built in 1998 and meticulously cared for this spacious 3 ...
From $379 per night (USD)
VRBO
From $404 per night (USD)
Expedia
Runaway Bills | 3 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
This stylish Conch Home is tucked away on a quiet lane in Old Town Key West. Surrounded by distinctive neighborhoods thi ...
From $404 per night (USD)
Expedia
$Henry's Piece of Paradise on the Ocean in Key West - Weekly \/ Nightly$
From $686 per night (USD)
VRBO
Henry's Piece of Paradise on the Ocean in Key West - Weekly \/ Nightly
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean vi ...
From $686 per night (USD)
VRBO
Click For Pricing
Expedia
Sunset views at the Galleon
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
You will be back year after year! Unit features full kitchen with Master King, Guest Twin Beds, and Pull out Sleeper Sof ...
Click For Pricing
Expedia
From $1108 per night (USD)
VRBO
Upper Bayview North: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1108 per night (USD)
VRBO
From $246 per night (USD)
Expedia
Upscale Townhouse with Golf and Lake Views, Shared Pool, WiFi, and AC - Dogs OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Tipsy Mermaid Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $246 per night (USD)
Expedia
From $561 per night (USD)
VRBO
Sunset South: First Floor 2 Bedroom 1 Bath Condo at Bayfront Suites & Marina
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $561 per night (USD)
VRBO
From $823 per night (USD)
Expedia
~HORSE CONCH~ Amazing location with shared pool and covered balcony!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
THE PROPERTY: Enjoy your stay in the tropics at Horse Conch, part of the highly touted "Queen Conch" complex, which incl ...
From $823 per night (USD)
Expedia
From $1038 per night (USD)
VRBO
Upper Bayview South: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1038 per night (USD)
VRBO
From $934 per night (USD)
Expedia
Middle Sunset: 3 Bedroom 3 Bath Luxury Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $934 per night (USD)
Expedia
From $1026 per night (USD)
VRBO
Bayview North One: Waterfront 4 Bedroom 4 Bath Condo at Bayfront Suites
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1026 per night (USD)
VRBO
From $1054 per night (USD)
Expedia
Sunset North: Luxury 4 Bedroom 4.5 Bath Condo at Bayfront Suites & Marina
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1054 per night (USD)
Expedia
From $982 per night (USD)
VRBO
Upper Sunset South: Luxury 3 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $982 per night (USD)
VRBO
From $1077 per night (USD)
Expedia
Bayview South: 4 Bedroom 3 Bath Waterfront Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1077 per night (USD)
Expedia
From $985 per night (USD)
VRBO
Upper Sunset North: Luxury 4 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $985 per night (USD)
VRBO
From $1108 per night (USD)
Expedia
Bayview Middle: Waterfront 3 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1108 per night (USD)
Expedia
From $159 per night (USD)
VRBO
coral stone
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our apartment offers all the comforts of home, 120 paces to Duval Street - shopping, restaurants and nightlife. Near Hem ...
From $159 per night (USD)
VRBO
From $962 per night (USD)
Expedia
~Serene Lily~ Luxurious 2 bed, 2.5 bath home in the upscale Truman Annex
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
WEEKLY RENTAL: This property has a 7 night minimum stay. THE PROPERTY: Located where the Gulf meets the Atlantic, this ...
From $962 per night (USD)
Expedia
From $190 per night (USD)
VRBO
Paradise found at the Key West Golf Club!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
We selected the best of everything to create paradise in Key West. Enjoy tropical breezes as you sip your morning coffee ...
From $190 per night (USD)
VRBO
From $669 per night (USD)
Expedia
Fantastic Fall Special - Act Fast, Open Nights Won't Last
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
City of Key West Business License # 28224 We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memo ...
From $669 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This 3 bedroom home is located one block from where Tennessee Williams home was located. The home has a true historic fl ...
From $240 per night (USD)
VRBO
Click For Pricing
Expedia
FANTASY WEEK
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale re ...
Click For Pricing
Expedia
From $306 per night (USD)
VRBO
Petite Pearl! Spacious 1 Bedroom, 1 Bath Pool Condo- RealKeyWest
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Petite Pearl, your hidden gem nestled in the heart of the coveted Meadows district in Key West. A stone's thr ...
From $306 per night (USD)
VRBO
From $1042 per night (USD)
Expedia
Historic Old Town Key West - Turtle House, Sleeps 6
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
OVERVIEW The Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described as ...
From $1042 per night (USD)
Expedia
From $387 per night (USD)
VRBO
Seaport Walkabout- the best location in town
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Open to annual rental at lower rate Two hundred yards from Schooner Wharf and the seaport and steps from Pepe’s in the ...
From $387 per night (USD)
VRBO
From $224 per night (USD)
Expedia
The Sylvia Gwynn, Key West Southernmost Point monthly vacation rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just 1 block from the action of Duval Street lies our newest space located at 1307 Whitehead Street. The Sylvia Gwynn is ...
From $224 per night (USD)
Expedia
From $1025 per night (USD)
VRBO
**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! COLORS OF THE ...
From $1025 per night (USD)
VRBO
From $480 per night (USD)
VRBO
The Key West Bougain Villa, a Monthly Vacation Rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Bougain Villa is found on Whitehead Street. Reserve a stay in this home located in the heart of historic Old Town Ke ...
From $480 per night (USD)
VRBO
From $407 per night (USD)
VRBO
~FISH CAMP!~ Family friendly, canal front, monthly rental.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $407 per night (USD)
VRBO
From $370 per night (USD)
Expedia
La Casita
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This beautiful, fully furnished 2BD/2BA single family home is located in the prestigious Casa Marina neighborhood. Speci ...
From $370 per night (USD)
Expedia
$Hidden Paradise-2bed 2bath condo w\/ ocean views, dock space, pool$
From $238 per night (USD)
VRBO
Hidden Paradise-2bed 2bath condo w\/ ocean views, dock space, 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 $238 per night (USD)
VRBO
From $771 per night (USD)
Expedia
Premier Ocean views, expansive balcony, renovated kitchen & bath 2024
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Penthouse property with vaulted ceilings at the famous 1800 Atlantic. Both bedrooms and the living room have access to y ...
From $771 per night (USD)
Expedia
From $180 per night (USD)
VRBO
Free Island Sprint has been transformed- Wonderful Renovation done in Fall 21
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Lovely 3rd floor interior courtyard view monthly rental. Enjoy the serenity of this bright and airy unit. This unit offe ...
From $180 per night (USD)
VRBO
From $1168 per night (USD)
Expedia
Casa Papa Del Mar on the Atlantic Spectacular views close to Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and ...
From $1168 per night (USD)
Expedia
From $511 per night (USD)
VRBO
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Moonlight" is a freshly renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from ...
From $511 per night (USD)
VRBO
From $226 per night (USD)
Expedia
Ocean Front Key West Oasis Island Tones Charming Historical Downtown area
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a ...
From $226 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Key West Paradise, Conch Hideaway, Island Vibrations, Balmy Ocean Breezes KWF
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through br ...
From $214 per night (USD)
VRBO
From $655 per night (USD)
Expedia
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished first-floor duplex home comes with Key West ...
From $655 per night (USD)
Expedia
From $663 per night (USD)
VRBO
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stunning 2 bedroom ocean-view oasis vacation rental at the fabulous 1800 Atlantic in Key West. Our family owned unit has ...
From $663 per night (USD)
VRBO
$Key West Beachfront Luxury 2\/2 Condo A212$
From $640 per night (USD)
Expedia
Key West Beachfront Luxury 2\/2 Condo A212
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 4 ...
From $640 per night (USD)
Expedia
From $175 per night (USD)
VRBO
Vibrant Island retreat, Expansive private balcony, Enjoy the Coastal Breezes
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Fabulous top floor ocean-view penthouse condo. Available during the Spring/Summer Season. Enjoy the Ocean-breeze's from ...
From $175 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Keys to Paradise: A 5-Star Beachside Retreat This beautiful 3-bedroom, 2-bath condo is located in a private beachside r ...
From $329 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Casa Coastal East – C231 After a recent remodel of the kitchen and bath, this unit underwent a total makeover with its n ...
From $214 per night (USD)
VRBO
From $1202 per night (USD)
Expedia
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Grand Vista - 2 bedroom suite - Totally renovated in 2022 - pictures coming soon. 2 Bedroom 2 bath suite, some re ...
From $1202 per night (USD)
Expedia
From $714 per night (USD)
VRBO
Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic 3rd Floor Ocean View Condominium Completely renovated, this unit features an entirely custom tiled unit. Full ...
From $714 per night (USD)
VRBO
From $689 per night (USD)
Expedia
Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
2 Bedroom, 2 Bath Garden View Condo at 1800 Atlantic, Key West This beautifully renovated condo features a king bed in ...
From $689 per night (USD)
Expedia
From $547 per night (USD)
VRBO
Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Anchor Drop 307 is an ocean view totally renovated top of the line unit. We have a brand new King mattress in the mast ...
From $547 per night (USD)
VRBO
From $668 per night (USD)
Expedia
Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautifully decorated two-bedroom, two-bath unit overlooks a tropical courtyard and garden area. The bathrooms have ...
From $668 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Joan's Caribbean Hideaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Just a few minutes from Key West, enjoy the peace and tranquility of this 2 story home, located in the Key West Golf Clu ...
From $313 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautifully renovated, this 2-bedroom, 2-bath penthouse offers stunning views of the Atlantic Ocean and Smathers Beach. ...
From $329 per night (USD)
Expedia
From $212 per night (USD)
VRBO
Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Lovely 2nd floor unit. Beautifully renovated, This unit has luxurious finishes. Both bedrooms and the living room open o ...
From $212 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar ...
From $215 per night (USD)
Expedia
From $200 per night (USD)
VRBO
Carolina to Keys Ocean view dream Monthly pricing Best pool on the Island
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautifully appointed 3rd floor ocean-view condo at the prestigious 1800 Atlantic Complex in Key West. This unit is an e ...
From $200 per night (USD)
VRBO
From $2722 per night (USD)
Expedia
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip ...
From $2722 per night (USD)
Expedia
From $216 per night (USD)
VRBO
Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a lovely 3rd floor partial ocean-view unit. You will love the spacious 50 ft private balcony that runs the lengt ...
From $216 per night (USD)
VRBO
$NEW!! Thirsty Mermaid - Large 4\/3 Pool Home - RealKeyWest$
From $572 per night (USD)
Expedia
NEW!! Thirsty Mermaid - Large 4\/3 Pool Home - RealKeyWest
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Thirsty Mermaid is located in the Casa Marina area just minutes from the Atlantic Ocean. This beautiful property has 2 f ...
From $572 per night (USD)
Expedia
$Old Town! Spacious Condo in Historic Home w\/Pool!$
From $266 per night (USD)
VRBO
Old Town! Spacious Condo in Historic Home w\/Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into ...
From $266 per night (USD)
VRBO
From $2276 per night (USD)
Expedia
**BRISA FRESCA @ THE ANNEX** Airy Home by Duval & Beach + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A trip to Key ...
From $2276 per night (USD)
Expedia
From $589 per night (USD)
VRBO
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! This ultimate ...
From $589 per night (USD)
VRBO
$**SMOOTH SAILING @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES..$
From $1295 per night (USD)
Expedia
**SMOOTH SAILING @ THE BEACH** Ocean Condo \/ Pool & Tennis + 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! Formerly La B ...
From $1295 per night (USD)
Expedia

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