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From $1759 per night (USD)
VRBO
Coconut Beach | Beach | Concierge | Pool | Gym
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coconut Beach Resort transports you to your very own private oasis, where the charm of old island architecture meets lus ...
From $1759 per night (USD)
VRBO
From $2148 per night (USD)
VRBO
Hyatt Beach | Concierge | Spa | Pool | Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your private sanctuary at Hyatt Beach House Resort, where the lush landscapes of Key West meet unparalleled l ...
From $2148 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 $1733 per night (USD)
VRBO
Sleeps 6 | Hyatt | Lux Resort | Concierge | Pool | Spa
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set along the stunning Atlantic Ocean, Hyatt Windward Pointe Resort seamlessly blends Key West’s laid-back vibe with mod ...
From $1733 per night (USD)
VRBO
From $1771 per night (USD)
VRBO
Sleeps 6 | Lux Resort | Hot Tub | Pool | Concierge
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your private sanctuary at Hyatt Beach House Resort, where the lush landscapes of Key West meet unparalleled l ...
From $1771 per night (USD)
VRBO
From $900 per night (USD)
Expedia
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 $900 per night (USD)
Expedia
From $809 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Dream Getaway at the Beach House Resort+Amenities. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Key West Paradise at the Beach House Resort Retreat! 🏖️ Additional $ ...
From $809 per night (USD)
VRBO
From $5625 per night (USD)
Expedia
Key West Florida Charming 1-bedroom resort with WiFi, AC
Bedrooms:
1
Bathrooms:
1
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 $5625 per night (USD)
Expedia
Hyatt Beach House Resort Key West 2-bedroom with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your private sanctuary in the lush landscape of Key West. Imagine old-fashioned screen-enclosed porches, gard ...
From $5625 per night (USD)
Expedia
From $5625 per night (USD)
VRBO
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)
VRBO
From $825 per night (USD)
Expedia
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 $825 per night (USD)
Expedia
$Helluva Happy Place | Escape to Old Town Key West - 3 bed\/2.5 bath townhome with private pool$
From $305 per night (USD)
VRBO
Helluva Happy Place | Escape to Old Town Key West - 3 bed\/2.5 bath townhome with private pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to Old Town Key West and indulge in a monthly retreat at our charming 3-bedroom, 2.5-bathroom townhome. Nestled i ...
From $305 per night (USD)
VRBO
Click For Pricing
Expedia
ROYAL POINCIANA COTTAGE - Quaint Old Town location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Royal Poinciana is a studio cottage with a queen bed, kitchen ,and private bath. The queen bed sleeps 2 people and the k ...
Click For Pricing
Expedia
From $400 per night (USD)
VRBO
Oceanfront Splendor @ the Key West Beach Club
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
29 NIGHT MINIMUM RENTAL ... This property is not allowed to accept pets. Enjoy endless views of the tranquil waters of ...
From $400 per night (USD)
VRBO
$Life is a Breeze at Windward Breeze by RENT KEY WEST VACATIONS - 2\/2 townhome -$
From $528 per night (USD)
Expedia
Life is a Breeze at Windward Breeze by RENT KEY WEST VACATIONS - 2\/2 townhome -
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Windward Breeze is part of the Windward Park gated community just off Simonton Street, one block from Duval Street. Ther ...
From $528 per night (USD)
Expedia
From $1064 per night (USD)
VRBO
Relax in Style at Windsor Townhomes #4
Bedrooms:
4
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 $1064 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Rent at PORCHSIDE PARADISE - Steps to Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Porchside Paradise is located in the front section of the Conch Republic Cottages. This beautiful home-away-from-home fe ...
From $316 per night (USD)
Expedia
From $258 per night (USD)
VRBO
In the heart of Old Town lies the HAVEN HOUSE
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Haven House provides the perfect home base to be near the center of everything but be able to retreat to home and watch ...
From $258 per night (USD)
VRBO
From $389 per night (USD)
Expedia
Half block to Duval @ Mango Hideaway -studio apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Mango Hideaway is comfortable junior suite, with sofa sitting area with adjoining king bedroom. The suite features ...
From $389 per night (USD)
Expedia
$ALOHA - Large 1 level 4bd\/4ba Monthly Rental$
From $439 per night (USD)
VRBO
ALOHA - Large 1 level 4bd\/4ba Monthly Rental
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Aloha is a stunning private residence on corner lot in the Casa Marina District. Updated 2 years ago, this beautiful hom ...
From $439 per night (USD)
VRBO
$Eyebrow Suite - 2bd\/1.5ba Suite off Duval$
From $522 per night (USD)
Expedia
Eyebrow Suite - 2bd\/1.5ba Suite off Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Eyebrow Suite is a spacious two-bedroom suite with one of the best locations on the island. Its large front porch and pa ...
From $522 per night (USD)
Expedia
$Spacious Townhome on Windsor Lane 3\/3.5$
From $1069 per night (USD)
VRBO
Spacious Townhome on Windsor Lane 3\/3.5
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Welcome to Windsor Townhomes #3! Once you enter this beautifully decorated oasis…your vacation begins. This townhome has ...
From $1069 per night (USD)
VRBO
From $204 per night (USD)
Expedia
ESPERANZA SUITE Monthly Rental close to Duval
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Esperanza Suite is a bi-level suite with a very spacious upstairs king bedroom with a writing desk and chair and a color ...
From $204 per night (USD)
Expedia
Click For Pricing
VRBO
ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Robinson Crusoe Cottage is a one-bedroom cottage with a queen bed, sleeper sofa, kitchen, and private bath. The queen be ...
Click For Pricing
VRBO
$ANNA MARIA HAVEN - Renovated 3bd\/3ba Conch Monthly rental$
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
$Windsor Townhomes #6 - Large pool 3B\/3.5 bath, 3 blocks to Duval$
From $1128 per night (USD)
VRBO
Windsor Townhomes #6 - Large pool 3B\/3.5 bath, 3 blocks to Duval
Bedrooms:
4
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 $1128 per night (USD)
VRBO
From $1217 per night (USD)
Expedia
MERMAID COVE - A collection of four units on Duval
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Mermaid Cove features four separate units (two cottages and two apartments), each with a private entrance and all decora ...
From $1217 per night (USD)
Expedia
$THALIA'S RETREAT @ Duval Square 2bd\/2ba townhome$
From $516 per night (USD)
VRBO
THALIA'S RETREAT @ Duval Square 2bd\/2ba townhome
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parkin ...
From $516 per night (USD)
VRBO
From $1436 per night (USD)
Expedia
No secrets at Pilar's Secret - Just a great location!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Pilar’s Secret is hidden away in the heart of Old Town Key West just half a block off the famous Duval Street. This secl ...
From $1436 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Deckside Suite - Efficiency at its finest!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Efficiency at its finest! The Deckside Suite is the perfect vacation rental in Key West for those who are trying to get ...
From $307 per night (USD)
VRBO
$Tropical Village: The Southern Cross - Quiet & gated. Pool\/Porch\/Pet friendly$
From $670 per night (USD)
Expedia
Tropical Village: The Southern Cross - Quiet & gated. Pool\/Porch\/Pet friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
There are stars in the southern sky! The Southern Cross takes its name from the “crux” constellation that guided sailors ...
From $670 per night (USD)
Expedia
From $1608 per night (USD)
VRBO
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $1608 per night (USD)
VRBO
From $1169 per night (USD)
Expedia
A contemporary island gem that was formerly used as a bottling plant,
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
A contemporary island gem that was formerly used as a bottling plant, this modern and spacious home is now a desirable t ...
From $1169 per night (USD)
Expedia
From $614 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 $614 per night (USD)
VRBO
From $837 per night (USD)
Expedia
Escape to the wonderful Cuban Paradise!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Built in 1917 as a “club” for Cuban cigar makers and their families as their home-away-from-home, this building soon bec ...
From $837 per night (USD)
Expedia
From $441 per night (USD)
VRBO
Key West at Ocean’s Corner!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Whether you want to explore the historic sites, enjoy the nightlife, or relax in nature, you’ll find it all during your ...
From $441 per night (USD)
VRBO
$Escape to \Oasis on 18th\ w\/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary!$
From $354 per night (USD)
Expedia
Escape to \"Oasis on 18th\" w\/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to your own private paradise at "Oasis on 18th," a luxurious three-bedroom, three-bathroom haven nestled within t ...
From $354 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Last Mango Beach Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience the allure of La Brisa Penthouse! Step into this captivating two-bedroom, two-bathroom condo nestled within t ...
From $404 per night (USD)
VRBO
From $610 per night (USD)
VRBO
Beach Club #112 - Unique Oceanfront living
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $610 per night (USD)
VRBO
From $2140 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 $2140 per night (USD)
VRBO
From $1189 per night (USD)
Expedia
Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1189 per night (USD)
Expedia
From $1664 per night (USD)
VRBO
Sunset Harbor Resort & Spa, Hot Tub, Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1664 per night (USD)
VRBO
$Escape to \Casa Escondida\$
From $403 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 $403 per night (USD)
Expedia
From $398 per night (USD)
VRBO
Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Time to fish, relax, and unwind! Bring your family & friends to this spacious 1,350 sqft waterfront corner cond ...
From $398 per night (USD)
VRBO
$OASIS SOUTH~Stunning 5 BR\/3 Ba w\/ Pool!$
From $361 per night (USD)
Expedia
OASIS SOUTH~Stunning 5 BR\/3 Ba w\/ Pool!
Bedrooms:
3
Bathrooms:
7
Sleeps:
14
BRING THE WHOLE GANG... If you and your large band of loved ones are looking for the perfect gathering in southernmost ...
From $361 per night (USD)
Expedia
$THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w\/ Pool!$
From $311 per night (USD)
VRBO
THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w\/ Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
HIDDEN GEM... The perfect location for guests who want to walk and bike to everything Key West has to offer. Modern cot ...
From $311 per night (USD)
VRBO
From $486 per night (USD)
Expedia
POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching!
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
EXQUISITE MODERN FAMILY COMPOUND... If a large home with all the modern luxuries is a must for your next island getaway, ...
From $486 per night (USD)
Expedia
$SWEET LIKE SUMMERTIME ~ 3 BR\/2Ba Home w\/ Pool and Yard!$
From $336 per night (USD)
VRBO
SWEET LIKE SUMMERTIME ~ 3 BR\/2Ba Home w\/ Pool and Yard!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
CLASSIC CHARMER... Welcome to this beautifully renovated 3 bedroom 2 bath pool home, located in Bahama Village. This cla ...
From $336 per night (USD)
VRBO
$McCartney's Manor - Deluxe K Suite W\/Pvt. Spa!$
From $460 per night (USD)
Expedia
McCartney's Manor - Deluxe K Suite W\/Pvt. Spa!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cool pastel, Caribbean inspired decor with original art throughout by Robin Hix. Bose speaker, Alexa Echo, full kitche ...
From $460 per night (USD)
Expedia
From $208 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 $208 per night (USD)
VRBO
Click For Pricing
Expedia
Ocean view apartment on coconut resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Coconut Beach Resort once belonged to the late Senator John Spottswood. He originally purchased the property because of ...
Click For Pricing
Expedia
From $194 per night (USD)
VRBO
CASA DE CANAL ~ 3 BR, 2 Ba. Canal Front Home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
KEY WEST BOATER'S BONANZA... This waterfront gem is a dream for boating and fishing enthusiasts. Indulge in all your nau ...
From $194 per night (USD)
VRBO
From $291 per night (USD)
Expedia
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)
Expedia
From $311 per night (USD)
VRBO
THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
COZY VALUE IN TRUMAN ANNEX… This 2nd Floor one bedroom, one bath condo is located in The Shipyard, a neighborhood of the ...
From $311 per night (USD)
VRBO
From $157 per night (USD)
Expedia
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
CLASSIC AND COZY... Exhale your worries away as you approach this delightful condo, one of four that are situated insid ...
From $157 per night (USD)
Expedia
From $149 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 $149 per night (USD)
VRBO
From $371 per night (USD)
Expedia
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Our Home Away from home. Our condo is located in the LaBrisa complex which is a GATED COMMUNITY across from ...
From $371 per night (USD)
Expedia
From $132 per night (USD)
VRBO
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 $132 per night (USD)
VRBO
From $436 per night (USD)
Expedia
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 $436 per night (USD)
Expedia
From $931 per night (USD)
VRBO
Hyatt Residence Club - Key West, FL - 2 Bedroom Unit - Beach House Location!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience a tropical getaway designed in classic Key West style, o ering manicured gardens and panoramic views of the G ...
From $931 per night (USD)
VRBO
From $400 per night (USD)
Expedia
💲 HUGE DISCOUNT for 28 day OCEAN FRONT! 90 FT BALCONY💰
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Please contact the owner for stays less than 28 days before you try to book. Military Vouchers are Welcome! In Key We ...
From $400 per night (USD)
Expedia
From $578 per night (USD)
VRBO
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 $578 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Enjoy More Privacy in a Truman Annex End Unit Townhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Contact us about special Summer Rates! Absolute Best Location! Our Townhome is set in the tranquil verdant gardens of ...
From $385 per night (USD)
Expedia
From $734 per night (USD)
VRBO
Hyatt Sunset Harbor, overlooking the Gulf of Mexico; 2 bd villa!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Concierge Realty is proud to present luxury villas at Hyatt Sunset Harbor! **Reservations are available in weekly (7 ni ...
From $734 per night (USD)
VRBO
From $507 per night (USD)
Expedia
Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our Key West Condo, the Key West Cabana. This spacious well appointed 2 bedroom, 2 full bath condo that’s ri ...
From $507 per night (USD)
Expedia
$\Tranquility \ At Ann Street Gardens Steps From Duval$
From $534 per night (USD)
VRBO
\"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)
VRBO
From $619 per night (USD)
Expedia
Quintessential Key West Resort! Hyatt Windward Pointe two bedroom. Book now!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Concierge Realty is proud to present luxury villas at Hyatt Windward Pointe! **Reservations are available in weekly (7 ...
From $619 per night (USD)
Expedia
From $338 per night (USD)
VRBO
SMATHER'S BEACH, Deluxe 2 BR oceanview unit, GREAT RATES ,
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Oceanfront at Smathers Beach in beautiful Key West, Florida. Why pay for a hotel, when you can enjoy your own private o ...
From $338 per night (USD)
VRBO
$Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking$
From $2064 per night (USD)
Expedia
Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking
Bedrooms:
7
Bathrooms:
7
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 $280 per night (USD)
VRBO
Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport
Bedrooms:
2
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 $280 per night (USD)
VRBO
From $729 per night (USD)
Expedia
GARDEN HIDEAWAY ~ Beautiful lush landscaped oasis located in the Casa Marina!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
PARADISE AWAITS... This charming home is located in one of the most desirable locations in Key West, Casa Marina. Garden ...
From $729 per night (USD)
Expedia
$BONITA EN ROSA ~ Charming 2 Bedroom, 1 Bathroom Home w\/ Pool!$
From $211 per night (USD)
VRBO
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 $211 per night (USD)
VRBO
$LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w\/ Loft in Old Town!$
From $179 per night (USD)
Expedia
LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w\/ Loft in Old Town!
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 $179 per night (USD)
Expedia
From $355 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 $355 per night (USD)
VRBO
From $159 per night (USD)
Expedia
SEAPORT SANCTUARY ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!
Bedrooms:
1
Bathrooms:
2
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 $159 per night (USD)
Expedia
From $855 per night (USD)
VRBO
SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...
From $855 per night (USD)
VRBO
$GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w\/ Pool and Ocean Views!$
From $948 per night (USD)
Expedia
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w\/ Pool and Ocean Views!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
YOUR OCEANFRONT OASIS AWAITS... This remarkable and magical retreat is sure to provide all the R & R you need to refresh ...
From $948 per night (USD)
Expedia
From $765 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 $765 per night (USD)
VRBO
From $543 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 $543 per night (USD)
Expedia
$Relaxing Garden View Suite w\/ Cozy Bedding – 12 Minutes to Hemingway House$
From $233 per night (USD)
VRBO
Relaxing Garden View Suite w\/ Cozy Bedding – 12 Minutes to Hemingway House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $233 per night (USD)
VRBO
From $344 per night (USD)
Expedia
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
ADORING RETREAT ONE BLOCK FROM DUVAL… One bedroom gem on Simonton Street one block from Duval. One bedroom, one bathroo ...
From $344 per night (USD)
Expedia
$SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Annex Home w\/Private Heated Pool!$
From $989 per night (USD)
VRBO
SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Annex Home w\/Private Heated Pool!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
PREMIER TROPICAL RETREAT... Come spoil yourself in this conveniently located two-story home tucked away on a quiet lane ...
From $989 per night (USD)
VRBO
$STRIPES ~ Delightful Condo w\/Shared Pool in the Heart of Old Town Key West!$
From $1115 per night (USD)
Expedia
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 $1115 per night (USD)
Expedia
From $2110 per night (USD)
VRBO
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 $2110 per night (USD)
VRBO
From $469 per night (USD)
Expedia
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
PLEASE BE AWARE: This community is currently undergoing balcony repair property-wide potentially through April 2026. A ...
From $469 per night (USD)
Expedia
From $217 per night (USD)
VRBO
SEAS THE DAY~ Newly Built Townhome in Perfect Location with Community Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
IMMACULATE RETREAT... Beautifully designed townhouse located in the Southernmost Cabana Community of Key West just steps ...
From $217 per night (USD)
VRBO
From $1047 per night (USD)
Expedia
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
Bedrooms:
2
Bathrooms:
5
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 $1047 per night (USD)
Expedia
$ATLANTIC BREEZE ~ 2B\/2BA Renovated Retreat w\/ Pool, Fitness Area & Beach!$
From $500 per night (USD)
VRBO
ATLANTIC BREEZE ~ 2B\/2BA Renovated Retreat w\/ Pool, Fitness Area & Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
PLEASE BE AWARE: This community is currently undergoing balcony repair property-wide potentially through April 2026. A ...
From $500 per night (USD)
VRBO
From $272 per night (USD)
Expedia
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 $272 per night (USD)
Expedia
$MANGO MARGARITA~ 2 bedroom\/2.5 bath, heated private pool, and close to Duval!$
From $881 per night (USD)
VRBO
MANGO MARGARITA~ 2 bedroom\/2.5 bath, heated private pool, and close to Duval!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
LOCATION LOCATION LOCATION... Enjoy this convenient Old Town Location. Located a block from Duval and a short walk or b ...
From $881 per night (USD)
VRBO
From $1109 per night (USD)
Expedia
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
Bedrooms:
2
Bathrooms:
4
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 $1109 per night (USD)
Expedia
$CONCH HEAVEN ~ Stylish 2B\/2Ba, Sleeps 6 in Old Town w\/ Heated Cocktail Pool!$
From $826 per night (USD)
VRBO
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 $826 per night (USD)
VRBO
From $984 per night (USD)
Expedia
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
JUST OFF DUVAL... Private single family home with three bedrooms and three bathrooms. Open the rear French doors to a p ...
From $984 per night (USD)
Expedia
From $354 per night (USD)
VRBO
SEA LA VIE ~ Living in Complete Luxury in This Elegant Three Story Home!
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
THREE STORY GRANDEUR… Located in the Casa Marina District in Old Town. This home is elegant, yet quite the tropical del ...
From $354 per night (USD)
VRBO
From $350 per night (USD)
Expedia
ISLAND TIME ~ Fully Renovated Conch Home in a Great Old Town Location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
ISLAND TIME... Award-winning, fully-renovated 1924 traditional conch style home. Relax and watch the world pass by from ...
From $350 per night (USD)
Expedia
From $1218 per night (USD)
VRBO
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL.... Once you step through the threshold of this O ...
From $1218 per night (USD)
VRBO
From $1120 per night (USD)
Expedia
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A SWEET SURPRISE JUST OFF DUVAL... Private single family home with off street parking totaling three bedrooms, two and h ...
From $1120 per night (USD)
Expedia
$Perfect Staycation! Close to Local Attractions! Deluxe Room w\/ Pool View$
From $242 per night (USD)
VRBO
Perfect Staycation! Close to Local Attractions! Deluxe Room w\/ Pool View
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $242 per night (USD)
VRBO
From $513 per night (USD)
Expedia
GARDEN OASIS ~ Great Casa Marina Location with True Island Elegance!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
WHEN ONLY THE BEST WILL DO... Located in the Casa Marina Area of Key West known for spacious and elegant fine homes; the ...
From $513 per night (USD)
Expedia

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