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From $503 per night (USD)
VRBO
Condo on Duval with WiFi, Hot Tub, & Private Parking - Dogs OK
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Duval Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $503 per night (USD)
VRBO
From $380 per night (USD)
Expedia
Sunny Tropical Condo with WiFi & Pool - Close to Beachside Action
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Seashore at the Shipyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $380 per night (USD)
Expedia
From $708 per night (USD)
VRBO
Amazing condo with pool & hot tub - ideal for exploring Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunrise Suites - Cat Island Suite 205 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $708 per night (USD)
VRBO
From $130 per night (USD)
Expedia
Cute Dog-friendly Tropical Condo with AC, WiFi, & Shared Pool - Snowbirds OK
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Paradise Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $130 per night (USD)
Expedia
From $5037 per night (USD)
VRBO
Spacious dog-friendly retreat with 3 hot tubs - near Duval Street & the beach
Bedrooms:
6
Bathrooms:
6
Sleeps:
24
Southernmost Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $5037 per night (USD)
VRBO
From $557 per night (USD)
Expedia
Breezy Condo with Pool & Hot Tub, Private Parking & Great Location - Dog OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Bonaire Suite 210 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $557 per night (USD)
Expedia
From $936 per night (USD)
VRBO
Comfortable Condo with Pool, Private Balcony, & Beach Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Atlantic Ocean View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $936 per night (USD)
VRBO
From $429 per night (USD)
Expedia
Contemporary Dog-Friendly Cottage with Easy Beach Access & Shared Pool
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Old Town Garden Villas - Andros Suite Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $429 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Welcoming & Conveniently Located Dog-Friendly Home - Walk to Everything
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Olivia Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $222 per night (USD)
VRBO
From $431 per night (USD)
Expedia
Dog-friendly resort condo with pool & hot tub, private parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Saint Croix Suite 212 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $431 per night (USD)
Expedia
From $500 per night (USD)
VRBO
Dog-friendly condo in prime location - walk to dining & sights, near the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Frontier Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $500 per night (USD)
VRBO
From $1141 per night (USD)
Expedia
Southernmost View | Pool & H20 Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Southernmost View is a modern, luxurious waterfront home in a private seven-home gated community just steps fro ...
From $1141 per night (USD)
Expedia
From $1280 per night (USD)
VRBO
Lovely dog-friendly home with guest cottage & private pool - great location
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bahama House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $1280 per night (USD)
VRBO
Click For Pricing
Expedia
Dante's Marina Townhouse 2 bed 1.5 bath unit with a 5 minute walk to Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A short walk, just blocks away from all the sought-after action on Duval Street and near the infamous Dante's Pool at th ...
Click For Pricing
Expedia
From $571 per night (USD)
VRBO
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Amelia House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $571 per night (USD)
VRBO
$Peaceful condo in Duval Square\/Old Town with lush gardens, pool, & chic decor$
From $743 per night (USD)
Expedia
Peaceful condo in Duval Square\/Old Town with lush gardens, pool, & chic decor
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Casa Bonita at Duval Square R1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...
From $743 per night (USD)
Expedia
From $376 per night (USD)
VRBO
Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Leeward Isle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $376 per night (USD)
VRBO
From $628 per night (USD)
Expedia
Bright condo with charms of historic Key West - amazing walkable locale
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Casa Havana at Duval Square R22 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $628 per night (USD)
Expedia
From $557 per night (USD)
VRBO
**CONCH GET ENOUGH at The Truman Annex in Key West**
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Enjoy an early morning cup of coffee on your private bedroom balcony after being gently woken by the crowing of a wild r ...
From $557 per night (USD)
VRBO
From $2403 per night (USD)
Expedia
Key West Oasis - Truman Annex Estate
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Welcome to Key West Oasis! This beautiful and sophisticated estate checks all the boxes and is located on one of the mos ...
From $2403 per night (USD)
Expedia
$Modern 2BR Condo Old Town\/Balcony & Pool$
From $194 per night (USD)
VRBO
Modern 2BR Condo Old Town\/Balcony & Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
*28 day min stay* Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close ...
From $194 per night (USD)
VRBO
$Green Goddess - 4 BD\/3 BA Amazing 360 Degree Rooftop Views! RealKeyWest$
From $497 per night (USD)
Expedia
Green Goddess - 4 BD\/3 BA Amazing 360 Degree Rooftop Views! RealKeyWest
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the beauty of Key West's famous sunsets from the comfort of your own vacation home at The Green Goddess. This ...
From $497 per night (USD)
Expedia
$Lil' Bit | Adorable \Conch\ Home on Quiet Street!$
From $205 per night (USD)
VRBO
Lil' Bit | Adorable \"Conch\" Home on Quiet Street!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: - "Lil Bit" is a rare find in the historic Bahama Village neighborhood. - This classic "conch" home is modern ...
From $205 per night (USD)
VRBO
$Sky Suite on Duval | Condo w\/Balcony$
From $791 per night (USD)
Expedia
Sky Suite on Duval | Condo w\/Balcony
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $791 per night (USD)
Expedia
From $2999 per night (USD)
VRBO
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! All year long ...
From $2999 per night (USD)
VRBO
From $940 per night (USD)
Expedia
Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
OVERVIEW The Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, ...
From $940 per night (USD)
Expedia
From $689 per night (USD)
VRBO
Duval Dream Loft | Right on Duval!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $689 per night (USD)
VRBO
From $763 per night (USD)
Expedia
The Collins on Duval
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $763 per night (USD)
Expedia
From $898 per night (USD)
VRBO
Historic Old Town Key West Cigarmaker's Cottage - Conch House, Sleeps 5
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded a ...
From $898 per night (USD)
VRBO
$Fairway Villa w\/ Private Pool$
From $247 per night (USD)
Expedia
Fairway Villa w\/ Private Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Fairway Villa a beautiful large 3 bedroom, 3 bathroom townhouse on the Key West Golf Course. This one of a ...
From $247 per night (USD)
Expedia
From $844 per night (USD)
VRBO
**CARIBBEAN CHARM @ THE FOUNDRY** Villa Near Duval & Beach + 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! The sound of ...
From $844 per night (USD)
VRBO
From $7703 per night (USD)
Expedia
**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
Bedrooms:
15
Bathrooms:
13
Sleeps:
32
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Coordinating ...
From $7703 per night (USD)
Expedia
From $1455 per night (USD)
VRBO
Duval's Duet on Duval
Bedrooms:
2
Bathrooms:
6
Sleeps:
18
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $1455 per night (USD)
VRBO
$Old Town home a short walk to Duval\/Couples Oasis$
From $301 per night (USD)
Expedia
Old Town home a short walk to Duval\/Couples Oasis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Add this listing to your wishlist by clicking the ♥ in the upper right hand corner. This 1 bedroom/1.5 bathroom ...
From $301 per night (USD)
Expedia
$Relaxing island home\/Great location\/Stylish$
From $341 per night (USD)
VRBO
Relaxing island home\/Great location\/Stylish
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Only 4 short blocks to Duval, this 1 bedroom/1.5 bathroom home is walking distance to your favorite Key West sp ...
From $341 per night (USD)
VRBO
$NEW! Completely Renovated \/ Close to Everything$
From $361 per night (USD)
Expedia
NEW! Completely Renovated \/ Close to Everything
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Located in the Heart of Historic Old Town Monthly Rental Pet Friendly.Up to 2 dogs, 40 lbs. max each. La Cala is a Newl ...
From $361 per night (USD)
Expedia
From $832 per night (USD)
VRBO
MILLIONAIRES ROW GREAT PRICES 4 BR, pool, free Wi-Fi, convenient to Duval St.
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for ...
From $832 per night (USD)
VRBO
$Central walk-up studio with partial ac - walk to Duval Street bars\/dining$
From $308 per night (USD)
Expedia
Central walk-up studio with partial ac - walk to Duval Street bars\/dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Truman @ Duval - Unit E Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $308 per night (USD)
Expedia
From $2784 per night (USD)
VRBO
**MAYA’S SECRET TREASURE @ DUVAL** Private Pool & Balcony over Duval + LAST KEY
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Walking along ...
From $2784 per night (USD)
VRBO
From $394 per night (USD)
Expedia
The Emelina, Key West Monthly Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Emelina is located in a beautiful historic home. This unit is luxuriously appointed with elegant materials and impe ...
From $394 per night (USD)
Expedia
$SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w\/ Kitchen and Shared Pool!$
From $593 per night (USD)
VRBO
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w\/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
SULTRY GARDEN SANCTUARY... Steal away from reality and find your way to the quintessential, tropical & adults only Trave ...
From $593 per night (USD)
VRBO
$COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen & Shared Pool!$
From $437 per night (USD)
Expedia
COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen & Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
BOTANICAL MAGIC AWAITS YOU... Only three blocks from all of the fine dining and entertainment of Duval Street, yet tucke ...
From $437 per night (USD)
Expedia
$Charming 'Boho Breeze' Retreat w\/ Pool Access$
From $169 per night (USD)
VRBO
Charming 'Boho Breeze' Retreat w\/ Pool Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $169 per night (USD)
VRBO
$ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen and Shared Pool!$
From $442 per night (USD)
Expedia
ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
ESCAPE TO A BOTANICAL HIDEAWAY... Immerse yourself at the charming adults only Travelers Palm Inn with unique suites and ...
From $442 per night (USD)
Expedia
From $548 per night (USD)
VRBO
ISLAND OASIS in the Truman Annex
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. | The living area is the ent ...
From $548 per night (USD)
VRBO
From $758 per night (USD)
Expedia
Sea Esta Suite | Pool on Duval
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: - In the middle of Duval Street and walking distance to the Southernmost Point! - Bright & airy two-story townh ...
From $758 per night (USD)
Expedia
From $180 per night (USD)
VRBO
NEW MONTHLY RENTAL, Old Town, Duplex, private backyard, pets welcome
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Sea Monkey and The Mermaid. Our home is a duplex located in Old Town and full of Key West charm. Walk to a ...
From $180 per night (USD)
VRBO
$Conch Cottage, Near Downtown! | Quiet w\/ Shared Pool$
From $151 per night (USD)
Expedia
Conch Cottage, Near Downtown! | Quiet w\/ Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Escape to this cozy Key West Cottage and enjoy all the island has to offer! Whether you plan to stay in or go o ...
From $151 per night (USD)
Expedia
From $692 per night (USD)
VRBO
Enjoy Old Town Key West in this Beautifully furnished house
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
We recently bought this house because we LOVE Key West! It is a 2 story Key West style house. The bedrooms are upstair ...
From $692 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Yellow Room at Grand Maloney by Brightwild
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 $360 per night (USD)
Expedia
From $359 per night (USD)
VRBO
Blue Room at the Grand Maloney by Brightwild
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 $359 per night (USD)
VRBO
From $391 per night (USD)
Expedia
Green Room at the Grand Maloney by Brightwild
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $391 per night (USD)
Expedia
From $468 per night (USD)
VRBO
Poolside King Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-size ...
From $468 per night (USD)
VRBO
From $417 per night (USD)
Expedia
Poolside Queen Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for thos ...
From $417 per night (USD)
Expedia
From $542 per night (USD)
VRBO
One Bedroom Deck Villa Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $542 per night (USD)
VRBO
From $303 per night (USD)
Expedia
Duval Street Suite on Duval Free Parking and Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Cuban Club Suite is a one bedroom (queen) 1 bath suite with a queen murphy bed and kitchen. Overlooking Duval ...
From $303 per night (USD)
Expedia
From $399 per night (USD)
VRBO
Duval Street Suite full kitchen, parking, & pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Key West Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic O ...
From $399 per night (USD)
VRBO
From $361 per night (USD)
Expedia
Duval Street Suites full kitchen, parking, pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Paradise Suite is a one bedroom (king bed) 1 bath suite with a murphy bed (queen) and kitchen. In historic Old ...
From $361 per night (USD)
Expedia
From $316 per night (USD)
VRBO
Duval Street Suite full kitchen and pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Little Palm Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlookin ...
From $316 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Duval Street Suite with full kitchen pool, parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking Duv ...
From $353 per night (USD)
Expedia
From $3379 per night (USD)
VRBO
6 BR 6 BA Guesthouse Suites on Duval parking, pool
Bedrooms:
6
Bathrooms:
6
Sleeps:
24
Summary: This can accommodate 24 people, each apartment has 2 beds. You'll have privacy with 6 individual suites each eq ...
From $3379 per night (USD)
VRBO
$MONTHLY RENTAL, Old Town, Duplex, private yard, 2 BR\/2 BA$
From $181 per night (USD)
Expedia
MONTHLY RENTAL, Old Town, Duplex, private yard, 2 BR\/2 BA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West charm. Both unit ...
From $181 per night (USD)
Expedia
From $589 per night (USD)
VRBO
Poolside Suite | Pool & Parking
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Poolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the hear ...
From $589 per night (USD)
VRBO
From $400 per night (USD)
Expedia
AWAY FROM IT ALL @ The Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $400 per night (USD)
Expedia
From $647 per night (USD)
VRBO
Galleon Resort beach hotel luxury in Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $647 per night (USD)
VRBO
From $1385 per night (USD)
Expedia
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfor ...
From $1385 per night (USD)
Expedia
From $1992 per night (USD)
VRBO
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + 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! Key West is k ...
From $1992 per night (USD)
VRBO
$Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio at Mile Marker 0!$
From $390 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio at Mile Marker 0!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $390 per night (USD)
Expedia
From $536 per night (USD)
VRBO
Pool View & Pvt Balcony | Samana Cay Suite
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $536 per night (USD)
VRBO
From $604 per night (USD)
Expedia
The Grand Turk | Sunset View & Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: - Welcome to the fun-filled Sunrise Suites complex located on the quiet side of Key West. - Just 1 mile from th ...
From $604 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Duval Street Suite full kitchen Old Town with pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Key Lime Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and full kitchen complete w ...
From $296 per night (USD)
VRBO
From $657 per night (USD)
Expedia
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Where the Ocean Meets the Windswept is nothing like . You don't have to spend a fortune to enjoy a spacious, clean and ...
From $657 per night (USD)
Expedia
From $516 per night (USD)
VRBO
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Caribbean Conch is a fantastic rental with a prime location near the pool. This unit features an extra-large floor plan, ...
From $516 per night (USD)
VRBO
From $544 per night (USD)
Expedia
Rent a Piece of Paradise, Best Location on the Island!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $544 per night (USD)
Expedia
Click For Pricing
VRBO
Close enough to Bike Ride to Mallory Square,far away to sleep during FantasyFest
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Coconut Mallory Resort and marina has multiple amenities including two pools, hot tubs, open air restaurant and bar, mar ...
Click For Pricing
VRBO
From $527 per night (USD)
Expedia
The Trinidad | Pool View & Parking
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 $527 per night (USD)
Expedia
From $448 per night (USD)
VRBO
The Palms...A beautiful space in the perfect place.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The perfect space in the perfect place. A quiet oasis on the 2nd floor nestled amongst palm trees in the shipyard secti ...
From $448 per night (USD)
VRBO
From $774 per night (USD)
Expedia
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home & Pool + LAST KEY SERVICES.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a month i ...
From $774 per night (USD)
Expedia
From $722 per night (USD)
VRBO
A BANANA REPUBLIC in Old Town Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
A Banana Republic Gem. This Old Town house may be the nicest property in Key West. Totally redone and professionally dec ...
From $722 per night (USD)
VRBO
From $1842 per night (USD)
Expedia
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + 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! Throughout Ke ...
From $1842 per night (USD)
Expedia
From $532 per night (USD)
VRBO
The Barbados | Balcony & Pool View!
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 $532 per night (USD)
VRBO
From $678 per night (USD)
Expedia
Harbor Walk Hideaways - Atocha Cottage | Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Atocha is part of the quiet complex called "Harbor Walk Hideaways," located in the Historic Seaport district of ...
From $678 per night (USD)
Expedia
$Bright Key West House with Private Pool, Gas Grill, W\/D, Central AC, & Free WiFi$
From $705 per night (USD)
VRBO
Bright Key West House with Private Pool, Gas Grill, W\/D, Central AC, & Free WiFi
Bedrooms:
6
Bathrooms:
4
Sleeps:
8
Tropical Vibes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $705 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Atlantic Ocean Breezes, Tropical Island Sunrises, Downtown 10 minutes away
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience elegant sophistication in this stunning 2-bedroom, 2-bathroom ocean-view condominium at the premier 1800 Atla ...
From $234 per night (USD)
Expedia
From $300 per night (USD)
VRBO
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You will love our piece of paradise. Our home away from home is tiled throughout. All new furnishings in 2017. Large fla ...
From $300 per night (USD)
VRBO
$Contra House | Luxury Home w\/Pool$
From $3772 per night (USD)
Expedia
Contra House | Luxury Home w\/Pool
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $3772 per night (USD)
Expedia
From $471 per night (USD)
VRBO
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
LOCATION, LOCATION, LOCATION! Located on a picturesque Old Town street, in one of the most desirable areas of the hist ...
From $471 per night (USD)
VRBO
$Key West Cabana-Old Town Key West- Steps to Duval Street w\/ Pool & Tiki Bar$
From $587 per night (USD)
Expedia
Key West Cabana-Old Town Key West- Steps to Duval Street w\/ Pool & Tiki Bar
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Key West Cabana welcomes you to our quaint 2 bedroom, 2 bathroom home with large private pool, assigned parking for 2 ca ...
From $587 per night (USD)
Expedia
From $520 per night (USD)
VRBO
The Andros | 4th Floor Sunset View
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 $520 per night (USD)
VRBO
From $585 per night (USD)
Expedia
Happy’s Houseboat Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This beautiful houseboat is the best way to stay in Key West. Recently Featured in Old Dominion‘s music video “I was on ...
From $585 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Bohemian Breeze @ Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $404 per night (USD)
VRBO
From $2270 per night (USD)
Expedia
Sublime Sunsets Waterfront Condo at The Truman Annex in Key West
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Breathtaking waterfront view from this 4 bedroom, 4.5 bath condominium in Harbour Place in the Truman Annex is ready to ...
From $2270 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Centrally located cottage apartment with patio - walk to beach & dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Bottoms Up Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $181 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Private Paradise with Heated Waterfall Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Time to sit back and relax! Paradise found in this completely redone home in Key West. Private outdoor heated pool, show ...
From $279 per night (USD)
Expedia
From $366 per night (USD)
VRBO
Cozy condo with free WiFi & fantastic location in central Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Truman @ Duval - Unit C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $366 per night (USD)
VRBO
From $410 per night (USD)
Expedia
Gorgeous Home with Lush Patio & Private Pool - Two Blocks to Higgs Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Sunshine Drive Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $410 per night (USD)
Expedia
From $793 per night (USD)
VRBO
AFTERNOON DELIGHT at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This amazing 2 bedroom/2 bath condo has one of the best views in Key West. Located in the historic Mills Place in Truman ...
From $793 per night (USD)
VRBO
$**SWEET AMERICANA @ OLD TOWN** 8BR\/8BA Compound + 2 Pools + LAST KEY SERVICES…$
From $5557 per night (USD)
Expedia
**SWEET AMERICANA @ OLD TOWN** 8BR\/8BA Compound + 2 Pools + LAST KEY SERVICES…
Bedrooms:
10
Bathrooms:
8
Sleeps:
20
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! It doesn't ge ...
From $5557 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Julia's Secret
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Best location in Key West! Just steps from the world class shops and restaurants of world famous Duval Street. There are ...
From $240 per night (USD)
VRBO
From $270 per night (USD)
VRBO
A+ Location in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The house has beautiful vaulted high ceilings. Along with the en-suite there is also another bathroom on the 1st floor a ...
From $270 per night (USD)
VRBO

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