Fleming Key Rentals
From $403 per night (USD)VRBO
Stunning Key West Stay Perfect for a Romantic Escape! Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $403 per night (USD)VRBO
From $186 per night (USD)Expedia
Charming 2-bedroom House in Historic Key West with Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Embrace the Enchantment of Old Key West Charm! Escape to the enchanting world of Key West Hideaway, where history meets ...
From $186 per night (USD)Expedia
From $651 per night (USD)VRBO
Coco's Poolside Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Coco's Poolside Retreat is a 3-story Key West vacation rental townhouse situated in a one-of-a-kind private tropical poo ...
From $651 per night (USD)VRBO
From $1352 per night (USD)Expedia
The Flower Power House - Boho Beautiful
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
Boho beautiful, the free-spirited presence of the Key West Flower Power House vacation rental, has much more in common w ...
From $1352 per night (USD)Expedia
From $314 per night (USD)VRBO
Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Palm Isle! A tropical 2nd-floor condo in the charming Meadows area of Key West. Relax on your private front ...
From $314 per night (USD)VRBO
From $236 per night (USD)Expedia
Gypsyginny's Hideaway in downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Set in the heart of Key West's vibrant Meadows district, this delightful 3-bedroom vacation rental on iconic White Stree ...
From $236 per night (USD)Expedia
From $947 per night (USD)VRBO
Meadows Manor | Elegant Oasis with Private Pool & Parking! Weekly Rental
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Meadows Manor | Elegant Oasis with Private Pool & Parking Discover the perfect blend of luxury and tranquility at the M ...
From $947 per night (USD)VRBO
From $394 per night (USD)Expedia
Poolside Hide-Away @ Palm Gardens offered by Rent Key West Vacations
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Poolside Hide-Away is a first floor one bedroom, one bath historic condo, that can accommodate up to 4 people, with wrap ...
From $394 per night (USD)Expedia
From $544 per night (USD)VRBO
~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Welcome to your private rocking chair front porch and tropical, Adult Only setting! As you enter your quai ...
From $544 per night (USD)VRBO
From $212 per night (USD)Expedia
WASTIN' A WAYLAND ~ Renovated 2 BR/2 Ba Home in Old Town!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
OLD TOWN GEM... This 2 bedroom, 2 bathroom cutie resides down a charming lane surrounded by historic residences and is a ...
From $212 per night (USD)Expedia
From $1167 per night (USD)VRBO
**The Three Mermaids @ Solaris Hill** New Construction Compound + Last Key Servi
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finding a com ...
From $1167 per night (USD)VRBO
From $224 per night (USD)Expedia
Cozy on Caroline - Key West Seaport
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the quintessential Key West lifestyle in this charming one-bedroom, two-bathroom apartment that perfectly bal ...
From $224 per night (USD)Expedia
From $222 per night (USD)VRBO
Seaport Serenity Cottage - Quiet and Quaint
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This charming 2BR/2BA rental is located in the Historic Seaport District offering off-street parking and a prime locatio ...
From $222 per night (USD)VRBO
From $448 per night (USD)Expedia
Tropical Island Retreat Near Florida Beaches with Pool & Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $448 per night (USD)Expedia
From $402 per night (USD)VRBO
Charming Hideaway with Pool – Walk to Duval St & Local Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $402 per night (USD)VRBO
From $358 per night (USD)Expedia
Cozy Key West Escape – Near Shops, Bars & Famous Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $358 per night (USD)Expedia
From $411 per night (USD)VRBO
Key West Comfort | Bungalow with Patio, 3 Pools & Steps to Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $411 per night (USD)VRBO
From $484 per night (USD)Expedia
Central Key West Stay | 3 Pools, Free Daily Breakfast, Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $484 per night (USD)Expedia
From $419 per night (USD)VRBO
Tropical Bungalow, 3 Pools, Breakfast Included, Pets Allowed, Near Shops & Bars
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $419 per night (USD)VRBO
From $395 per night (USD)Expedia
Pet-Friendly & Cozy Bungalow, Daily Breakfast & Poolside Lounging!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $395 per night (USD)Expedia
From $411 per night (USD)VRBO
Bungalow in Heart of Key West | 3 Pool, Free Breakfast, Shops & Bars Nearby
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $411 per night (USD)VRBO
From $381 per night (USD)Expedia
Key West Charm | 3 Pools, Complimentary Breakfast, Near Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $381 per night (USD)Expedia
From $563 per night (USD)VRBO
Key West Getaway | Romantic Bungalow, Pools, Breakfast & Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $563 per night (USD)VRBO
From $496 per night (USD)Expedia
The Penthouse at Custom House Inn | New! Coastal Escape on Duval Street!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Penthouse at Custom House Inn | Serene Coastal Escape on Duval Street! Immerse yourself in the calm and comfort of ...
From $496 per night (USD)Expedia
From $655 per night (USD)VRBO
Most Beautiful View on Key West?
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Make yourself at home in this 2-bedroom Key West retreat. This cool condo features a beautiful view from every room. Spa ...
From $655 per night (USD)VRBO
From $739 per night (USD)Expedia
Upscale 2-bedroom villa in the heart of Old Town. Minutes to Duval & Mallory Sq
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this upscale condo in Key West. This terrific property features 2 bedrooms with 1 king bed and 1 queen bed, a ...
From $739 per night (USD)Expedia
From $245 per night (USD)VRBO
Charming island cottage with sunny patio, modern kitchen, AC & dog friendly yard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Casa Sirena Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $245 per night (USD)VRBO
From $584 per night (USD)Expedia
COCKTAILS ON THE CORNER- 2 Bedroom / 1 Bathroom W/ Pool - Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Cocktails on the Corner! This 2- bedroom, 1- bathroom residence sits on the corner of Southard and Margaret S ...
From $584 per night (USD)Expedia
From $577 per night (USD)VRBO
Sandbar Suite | 2 bed/2 bath apartment with patio overlooking Front Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Sandbar Suite – 2BR/2BA Island Getaway with Front Street views Welcome to The Sandbar Suite, a bright and breezy 2- ...
From $577 per night (USD)VRBO
From $213 per night (USD)Expedia
Key Lime Hideaway- Traditional Key West Style House in Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Your Old Key West Oasis! Experience the charm of Old Key West in this stunning traditional Conch-style home. ...
From $213 per night (USD)Expedia
From $588 per night (USD)VRBO
KEY WEST- Amazing 3 rd floor corner unit overlooking Florida Bay and Yacht Club.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Consider this 3rd floor corner condo overlooking the Florida Bay and Yacht Club as your next vacation destination. Enjoy ...
From $588 per night (USD)VRBO
From $286 per night (USD)Expedia
LONE PALM COTTAGE ~ 3 BR, 2 Ba Home w/ 2 Cottages, Pool & Parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
OLD TOWN AMBIENCE.... This home with 2 mini cottages captures the essence of time-honored Key West living from the mome ...
From $286 per night (USD)Expedia
From $124 per night (USD)VRBO
Sunny Island Escape | 1 bed, 1 bath monthly rental in heart of Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the perfect island retreat in this beautifully updated one-bedroom, one-bath apartment located just steps from ...
From $124 per night (USD)VRBO
From $587 per night (USD)Expedia
The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Complex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Condo in Truman Annex Welcome to your sunny esc ...
From $587 per night (USD)Expedia
From $155 per night (USD)VRBO
Charming 1-bedroom apartment in Key West with AC, WiFi. Enjoy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your cozy getaway awaits in Key West at this brilliant apartment. This marvelous space features 1 bedroom with a queen b ...
From $155 per night (USD)VRBO
From $1824 per night (USD)VRBO
3| Galleon | Marina | Spa | Hot Tub | Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $1824 per night (USD)VRBO
From $2236 per night (USD)VRBO
Sunset Harbor | Marina | Hot Tub | Pool | Concierge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $2236 per night (USD)VRBO
From $1941 per night (USD)VRBO
The Banyan | Concierge | Beach Access | Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of historic Old Town Key West, The Banyan Resort is a charming escape set on a mid-1800s estate ste ...
From $1941 per night (USD)VRBO
From $11524 per night (USD)VRBO
Galleon | Hot Tub | Marina | Lux Resort | Concierge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $11524 per night (USD)VRBO
From $2236 per night (USD)VRBO
Sunset Harbor | Hyatt | Hot Tub | Pool | Marina | Lux Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $2236 per night (USD)VRBO
From $1839 per night (USD)VRBO
Galleon | Marina | Lux Resort | Pool | Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $1839 per night (USD)VRBO
From $1839 per night (USD)VRBO
Galleon | Marina | Concierge | Hot Tub | Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled along the sparkling Gulf of Mexico in historic Old Town, The Galleon Resort places you in the heart of Key West’ ...
From $1839 per night (USD)VRBO
From $818 per night (USD)VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $818 per night (USD)VRBO
From $5625 per night (USD)Expedia
Key West Hyatt Charming 2-bedroom resort with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)Expedia
From $5625 per night (USD)VRBO
Key West Studio Charming resort with WiFi, AC, fitness room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
From $378 per night (USD)Expedia
ANNA MARIA HAVEN - Renovated 3bd\/3ba Conch Monthly rental
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This newly remodeled Conch house is located on Olivia Street in Old Town Key West just two and a half blocks from World ...
From $378 per night (USD)Expedia
From $960 per night (USD)VRBO
Relax in Style at Windsor Townhomes #4
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a q ...
From $960 per night (USD)VRBO
From $1572 per night (USD)Expedia
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $1572 per night (USD)Expedia
From $367 per night (USD)VRBO
The Hideout! Where Luxury Meets Location. Fully Renovated, with Pool.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Hideout, where luxury meets location. Look no further than "The Hideout" for upscale luxury and single- ...
From $367 per night (USD)VRBO
From $927 per night (USD)Expedia
Spacious Townhome on Windsor Lane 3/3.5
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Windsor Townhomes #3! Once you enter this beautifully decorated oasis…your vacation begins. This townhome has ...
From $927 per night (USD)Expedia
From $938 per night (USD)VRBO
Windsor Townhomes #6 - Large pool 3B/3.5 bath, 3 blocks to Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a q ...
From $938 per night (USD)VRBO
From $385 per night (USD)Expedia
Escape to \"Casa Escondida\"
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to the enchanting "Casa Escondida," a historic Conch Style home with a modern twist, nestled on a tranquil, seclu ...
From $385 per night (USD)Expedia
From $3478 per night (USD)VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Galleon Resort in Key West, where paradise meets luxury at the southernmost tip of the United States. In ...
From $3478 per night (USD)VRBO
From $644 per night (USD)Expedia
Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to fish, relax, and unwind! Bring your family & friends to this spacious 1,350 sqft waterfront corner cond ...
From $644 per night (USD)Expedia
From $197 per night (USD)VRBO
Charming + Circa 1889 Historic Eyebrow Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 Night Minimum. Welcome to "The Saltbox"! Featured in design magazines. 710 Ashe Street is a charming house circa 18 ...
From $197 per night (USD)VRBO
From $155 per night (USD)Expedia
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
CLASSIC AND COZY... Exhale your worries away as you approach this delightful condo, one of four that are situated insid ...
From $155 per night (USD)Expedia
From $291 per night (USD)VRBO
Old Town Key West Live like a local
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Live like a local! This vacation flat is located at Mile marker 1, and sits nestled above the street right on Truman Av ...
From $291 per night (USD)VRBO
From $135 per night (USD)Expedia
Mango Tree Key West Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
True Key West flavor! 1 Bedroom 1 Bathroom apartment newly remodeled and updated Conch House located on White St.with h ...
From $135 per night (USD)Expedia
From $331 per night (USD)VRBO
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items ...
From $331 per night (USD)VRBO
From $644 per night (USD)Expedia
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $644 per night (USD)Expedia
From $147 per night (USD)VRBO
CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
SIMPLISTIC ELEGANCE... Enjoy easy island living in this quaint and cozy Key West gem located in the attractive community ...
From $147 per night (USD)VRBO
From $2064 per night (USD)Expedia
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $2064 per night (USD)Expedia
From $276 per night (USD)VRBO
Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Mojitoville is perfect for the discriminating guest who wants to enjoy close proximity to Key West's Historic Seaport wi ...
From $276 per night (USD)VRBO
From $534 per night (USD)Expedia
\"Tranquility \" At Ann Street Gardens Steps From Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location is ideal for this wonderful one bedroom retreat. A lush, inviting compound created so owners and guests could e ...
From $534 per night (USD)Expedia
From $321 per night (USD)VRBO
PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
PICTURE PERFECT PARADISE... This newly renovated retreat is nestled in the highly sought-after neighborhood of The Meado ...
From $321 per night (USD)VRBO
From $139 per night (USD)Expedia
SEAPORT SANCTUARY ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A QUIET BUNGALOW IN THE HISTORIC SEAPORT... Private one bedroom home in the heart of Old Town. A great place for a coup ...
From $139 per night (USD)Expedia
From $689 per night (USD)VRBO
SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...
From $689 per night (USD)VRBO
From $477 per night (USD)Expedia
The Most Perfect Old Town Key West Location for a Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroo ...
From $477 per night (USD)Expedia
From $626 per night (USD)VRBO
THE SEASHELL ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $626 per night (USD)VRBO
From $183 per night (USD)Expedia
BONITA EN ROSA ~ Charming 2 Bedroom, 1 Bathroom Home w/ Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $183 per night (USD)Expedia
From $145 per night (USD)VRBO
LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w/ Loft in Old Town!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $145 per night (USD)VRBO
From $150 per night (USD)Expedia
GILLEY'S PLACE ~ Fully Renovated 1 Bedroom, 1 Bath Cottage in Old Town!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
AN ESCAPE LIKE NO OTHER… Disconnect from the real world and reconnect with each other in this picture perfect, quaint co ...
From $150 per night (USD)Expedia
From $961 per night (USD)VRBO
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
THE HEART OF OLD TOWN... Charming Old Town home in the heart of Key West. Located on Southard Street just steps from Du ...
From $961 per night (USD)VRBO
From $725 per night (USD)Expedia
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
OLD TOWN LOCATION... A beautifully furnished and comfortable home, located just 5 short blocks to Duval Street. Have bi ...
From $725 per night (USD)Expedia
From $329 per night (USD)VRBO
ISLAND TIME ~ Fully Renovated Conch Home in a Great Old Town Location!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
ISLAND TIME... Award-winning, fully-renovated 1924 traditional conch style home. Relax and watch the world pass by from ...
From $329 per night (USD)VRBO
From $1012 per night (USD)Expedia
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL.... Once you step through the threshold of this O ...
From $1012 per night (USD)Expedia
From $853 per night (USD)VRBO
STRIPES ~ Delightful Condo w/Shared Pool in the Heart of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key W ...
From $853 per night (USD)VRBO
From $2103 per night (USD)Expedia
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
LUXURY IN OLD TOWN... Grand home in the Historic Seaport area of Old Town Key West. Tucked behind a canopy of palms this ...
From $2103 per night (USD)Expedia
From $730 per night (USD)VRBO
SAPODILLA HOUSE ~ Spectacular 3B/3.5Ba Annex Home w/Private Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PREMIER TROPICAL RETREAT... Come spoil yourself in this conveniently located two-story home tucked away on a quiet lane ...
From $730 per night (USD)VRBO
From $813 per night (USD)Expedia
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you do not need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key ...
From $813 per night (USD)Expedia
From $242 per night (USD)VRBO
HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
ISLAND TIME AWAITS… Step up to this serene, tropical cottage inviting you in with a multitude of swaying palms, a privat ...
From $242 per night (USD)VRBO
From $357 per night (USD)Expedia
Colony Poolside: A charming bungalow near Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter th ...
From $357 per night (USD)Expedia
From $216 per night (USD)VRBO
SEA-NIC VIEW ~ 2 BR/2Ba Water-front views, Heated Pool Access and Dockage!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
IT'S A SWELL LIFE… Endless island treasures engulf this oceanfront haven which is your one stop destination for a comple ...
From $216 per night (USD)VRBO
From $179 per night (USD)Expedia
Pearl in Paradise-Charming 2bed 2bath Old Town home w/ shared pool, parking
- 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 $179 per night (USD)Expedia
From $486 per night (USD)VRBO
Antigua Retreat- 2BR 2BA waterfront condo w/ pool & boat slip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $486 per night (USD)VRBO
From $381 per night (USD)Expedia
Ann Street Cottage: A bright and airy home near Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom c ...
From $381 per night (USD)Expedia
From $2173 per night (USD)VRBO
Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation re ...
From $2173 per night (USD)VRBO
From $922 per night (USD)Expedia
PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town K ...
From $922 per night (USD)Expedia
From $281 per night (USD)VRBO
CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD/2.5BA - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Description: Welcome to Corazon, a stunning 2-bedroom vacation rental in the heart of Key West's Old Town neighborhood. ...
From $281 per night (USD)VRBO
From $681 per night (USD)Expedia
Charming 3 bedroom blocks from Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This charming Conch Style home on Southard street is just a few blocks from Duval St and across from the old Harris Scho ...
From $681 per night (USD)Expedia
From $510 per night (USD)VRBO
Elizabeth Retreat: A three bedroom historic home in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just ...
From $510 per night (USD)VRBO
From $252 per night (USD)Expedia
Tropical oasis in a former author’s retreat. Sleeps 4.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Former residence of an author and decorated accordingly, this cute cottage is quintessential Key West. Perfect monthly r ...
From $252 per night (USD)Expedia
From $216 per night (USD)VRBO
Ashe Splashe: A beautiful restoration of a historic Key West property
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
28 DAY MINIMUM RENTAL From the owners of South of Frances, here is another beautiful, historic restoration project. Th ...
From $216 per night (USD)VRBO
From $574 per night (USD)Expedia
Old Town 4 /4.5 house with private pool and 2 poolside cottages + outdoor shower
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Newly restored Key West property in old town. Blocks from Duval and the harbor. Private heated pool central AC washer dr ...
From $574 per night (USD)Expedia
From $458 per night (USD)VRBO
CROOKED PALM ~ 3 Bedroom, 3 Bathroom Luxury Home w/ Pool & Compact Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
LET THE REAL WORLD SLIP AWAY... Experience quintessential island serenity within this charming and newly renovated home ...
From $458 per night (USD)VRBO
From $1040 per night (USD)Expedia
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BEGIN YOUR ISLAND ESCAPE... Come get lost in the magic of this captivating island retreat offering modern amenities with ...
From $1040 per night (USD)Expedia
From $549 per night (USD)VRBO
Incredible 2BR Penthouse condo on Front Street with amazing amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is one of Key West's best resorts. Located on Front Street in front of the Marina, it has a large wat ...
From $549 per night (USD)VRBO
From $313 per night (USD)Expedia
QUEEN OF SOL ~ 3 Bed, 2 Bath in Peaceful Neighborhood with Dip Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
YOUR PIECE OF PARADISE… Residing in an attractive neighborhood at the highest point of Key West referred to as “Solares ...
From $313 per night (USD)Expedia
From $529 per night (USD)VRBO
New Listing- Modern & spacious historic home with private pool and parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Discover paradise at Brisa Azul (Blue Breeze), an exquisite historic home nestled in the heart of Old Town Key West. Thi ...
From $529 per night (USD)VRBO
From $1715 per night (USD)Expedia
~ VILLA JOSINE ~ 4 B/4.5 BA large designer home with pool in a great location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Villa Josine not only has curb appeal but also is a stunning example of a Key West eyebrow house. This arc ...
From $1715 per night (USD)Expedia