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From $675 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 $675 per night (USD)
VRBO
From $612 per night (USD)
Expedia
The Secret Grotto
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Welcome to The Secret Grotto — Your Luxurious Tropical Escape! Step into this stunning 3,220-square-foot sanctuary nest ...
From $612 per night (USD)
Expedia
From $948 per night (USD)
VRBO
The Gideon Lowe House - Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Elegance. Sophistication. Perfection. Welcome to the Gideon Lowe House, a historic treasure in the heart of Old Town Ke ...
From $948 per night (USD)
VRBO
From $457 per night (USD)
Expedia
Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Keys to Paradise – Your Cozy Retreat in the Heart of Key West! Located in the charming Shipyard Condominium ...
From $457 per night (USD)
Expedia
From $1258 per night (USD)
VRBO
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $1258 per night (USD)
VRBO
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Expedia
Oceanfront Condo at Hyatt Windward Pointe
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
You won't find a better steal than a high-season stay in this beautiful and spacious second-floor condo on the Hyatt Win ...
Click For Pricing
Expedia
From $508 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 $508 per night (USD)
VRBO
From $866 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 $866 per night (USD)
VRBO
From $579 per night (USD)
VRBO
💲 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 $579 per night (USD)
VRBO
From $889 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 $889 per night (USD)
VRBO
From $638 per night (USD)
VRBO
Enjoy More Privacy in a Truman Annex End Unit Townhome
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Contact us about special Summer Rates! Absolute Best Location! Our Townhome is set in the tranquil verdant gardens of ...
From $638 per night (USD)
VRBO
From $147 per night (USD)
Expedia
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)
Expedia
From $905 per night (USD)
VRBO
Waterfront Home in Key Cove Landings
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $905 per night (USD)
VRBO
From $1072 per night (USD)
Expedia
Waterfront luxury home with private pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you’re looking for an upscale escape by the sea, 3/4 Time is your Key West hidden gem. Enjoy the island life in your ...
From $1072 per night (USD)
Expedia
From $938 per night (USD)
VRBO
Luxury Waterfront Home with private pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $938 per night (USD)
VRBO
From $1292 per night (USD)
Expedia
Modern Waterfront Luxury Home with Heated Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you’re looking for a luxury escape on the water, Paris Mango is your island gem. Named after Jimmy's "Last Mango in P ...
From $1292 per night (USD)
Expedia
From $1197 per night (USD)
VRBO
Conch style home in Oldtown with private pool AND dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...
From $1197 per night (USD)
VRBO
From $1335 per night (USD)
Expedia
Luxury Waterfront Home with Private Pool and Dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $1335 per night (USD)
Expedia
From $409 per night (USD)
VRBO
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
Bedrooms:
2
Bathrooms:
2
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 $409 per night (USD)
VRBO
$Sept.mid wk.spec.117. lod +\n10 min walk beach, close to all +\nfull kitch& patio$
From $255 per night (USD)
Expedia
Sept.mid wk.spec.117. lod +\n10 min walk beach, close to all +\nfull kitch& patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
SUMMER SPECIAL August and September Most dates @ 107. lodging plus extras per night. With 4 night stay 5th night FREE ...
From $255 per night (USD)
Expedia
From $1131 per night (USD)
VRBO
Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $1131 per night (USD)
VRBO
From $143 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 $143 per night (USD)
VRBO
Click For Pricing
VRBO
Two Bedroom Condo, Key West, Ocean View 3054374
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hyatt Residence Club Key West – Windward Pointe Two Bedroom Condo – Partial Ocean Views Partial ocean views and lavish ...
Click For Pricing
VRBO
From $710 per night (USD)
Expedia
Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home - Stay spacious in Key West. Boat ...
From $710 per night (USD)
Expedia
$Downtown Key West 2BR/2BA•Pool, Dock, Pet \Aruba\$
From $791 per night (USD)
VRBO
Downtown Key West 2BR/2BA•Pool, Dock, Pet \"Aruba\"
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Enjoy true space in Key West! This 1,200 sq ft waterfront condo offers a full kitchen, dining area, living room ...
From $791 per night (USD)
VRBO
From $1744 per night (USD)
VRBO
St. Johns Waterfront 4BR Penthouse•Pool•Dock•Park
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Bring the whole crew to this 2200 sqft waterfront penthouse—perfect for families & large groups! With 4 bedroom ...
From $1744 per night (USD)
VRBO
$Old Town \Eleuthera\ • 2BR Waterfront Corner Condo$
From $702 per night (USD)
VRBO
Old Town \"Eleuthera\" • 2BR Waterfront Corner Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just ...
From $702 per night (USD)
VRBO
From $162 per night (USD)
VRBO
Sunny Apartment with a Large Deck and Great View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming 1 bedroom second floor apartment with a large deck space for dining, sunbathing or watching sunsets. In residen ...
From $162 per night (USD)
VRBO
From $189 per night (USD)
VRBO
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 $189 per night (USD)
VRBO
Click For Pricing
Expedia
Hyatt Residence Club Windward Pointe Key West 2br/2ba/6ppl
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT Windward Pointe. Sleeps 6 people. 2 bedrooms (1King/1Quee ...
Click For Pricing
Expedia
From $369 per night (USD)
VRBO
Pool & Parking, & Pet Friendly - Hidden Oasis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Hidden Oasis is a 28-night minimum rental, offering contemporary luxury in the heart of Midtown, Key West. It’s ...
From $369 per night (USD)
VRBO
From $294 per night (USD)
Expedia
Charming, updated home near Duval St. with enclosed patio & walkable location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Coral Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $294 per night (USD)
Expedia
From $314 per night (USD)
VRBO
THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $314 per night (USD)
VRBO
From $1191 per night (USD)
VRBO
Experience Key West w/ Poolside Bar, Private Terraces & Free Shuttle Service!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $1191 per night (USD)
VRBO
From $1123 per night (USD)
VRBO
Ideal Family Stay in Great Location, 4 Pools, Shuttle Service, Near Airport!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $1123 per night (USD)
VRBO
From $487 per night (USD)
VRBO
Beautiful Water Views! Minutes to Southernmost Point! Parking, Onsite Pools!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $487 per night (USD)
VRBO
From $189 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 $189 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 $318 per night (USD)
VRBO
Coconut Cottage | Colorful abode with a full kitchen, enclosed patio, AC, & W/D
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Coconut Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $318 per night (USD)
VRBO
From $256 per night (USD)
Expedia
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 $256 per night (USD)
Expedia
From $653 per night (USD)
VRBO
**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR/3.5BA Condo & Pool + LAST KEY SERVI
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! MODERN MAJEST ...
From $653 per night (USD)
VRBO
From $471 per night (USD)
Expedia
The Elizabeth Suite | 1 bed, 1 bath w/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience the charm of historic Key West with a stay at The Elizabeth Suite, a recently renovated 1 bedroom, 1 bathroom ...
From $471 per night (USD)
Expedia
From $402 per night (USD)
VRBO
The Fleming Suite | 1 bed, 1 bath condo w/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to The Fleming Suite, a 1 bedroom, 1 bathroom vacation rental located at The Bayview House in vibrant Key West. ...
From $402 per night (USD)
VRBO
Click For Pricing
Expedia
New Listing-Golf Course Charmer!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
As you make your way into The Sweet Tee, an immediate sense of relaxation and vacation mode envelops you. The carefully ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Southern Skies, Stylish Home in Old Town Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space Experience the paradise of Southern Skies, an elegant 3 bedroom and 2.5 bath home nestled in the heart ...
Click For Pricing
VRBO
From $573 per night (USD)
VRBO
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. Blue tooth speaker, Alexa Echo, full ki ...
From $573 per night (USD)
VRBO
From $262 per night (USD)
VRBO
Breezy Key West First-Floor Condo w/ Pool Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience your next seaside vacation in style at this 2-bedroom, 2-bathroom Key West vacation rental. This 1st-floor co ...
From $262 per night (USD)
VRBO
From $367 per night (USD)
Expedia
**THE OSPREY'S NEST @ SUNRISE SUITES** Condo & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Want to be in ...
From $367 per night (USD)
Expedia
From $803 per night (USD)
VRBO
Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Time to fish, relax, and unwind! Bring your family & friends to this spacious 1,350 sqft waterfront corner cond ...
From $803 per night (USD)
VRBO
From $410 per night (USD)
Expedia
OASIS SOUTH~Stunning 5 BR/3 Ba w/ Pool!
Bedrooms:
2
Bathrooms:
5
Sleeps:
14
BRING THE WHOLE GANG... If you and your large band of loved ones are looking for the perfect gathering in southernmost ...
From $410 per night (USD)
Expedia
From $608 per night (USD)
VRBO
BE AS YOU ARE - 3 Bedroom / 3 Bathroom - Mid Town KEY WEST w/ POOL
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to “Be As You Are” – Your Perfect Key West Getaway Thoughtfully renovated and beautifully furnished with guest ...
From $608 per night (USD)
VRBO
From $497 per night (USD)
Expedia
SWEET LIKE SUMMERTIME ~ 3 BR/2Ba Home w/ Pool and Yard!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
CLASSIC CHARMER... Welcome to this beautifully renovated 3 bedroom 2 bath pool home, located in Bahama Village. This cla ...
From $497 per night (USD)
Expedia
From $1292 per night (USD)
VRBO
Waterfront Sunset Harbor Resort Near Old Town+Amenities: 2BR FindingMeili
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to FindingMeili🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! An Additional Savings from $500 ...
From $1292 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Our Piece of Paradise-
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your ideal Key West getaway! Perfect for families and ideally situated between Old Town, New Town, and Duval ...
From $402 per night (USD)
Expedia
From $631 per night (USD)
VRBO
Midnight Cowboy by AvantStay | 3 Artistic Spaces
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-ti ...
From $631 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Monkey House by AvantStay | Pool, by Duval Street
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Monkey House is a two-bedroom Key West escape that ...
From $307 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Tennessee Williams by AvantStay | Funky Design + Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Tennessee Williams is a one-of-a-kind Key West esca ...
From $248 per night (USD)
VRBO
From $405 per night (USD)
Expedia
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 $405 per night (USD)
Expedia
From $643 per night (USD)
VRBO
POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching!
Bedrooms:
5
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 $643 per night (USD)
VRBO
From $865 per night (USD)
Expedia
New Years special in gorgeous Bahama Village 4Bd 4.5 Ba all ensuite, 2x parking!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Welcome to Moveable Feast, a dreamy home in the heart of Bahama Village that sleeps 10 comfortably. Located on a quiet, ...
From $865 per night (USD)
Expedia
From $1033 per night (USD)
VRBO
Rooftop Penthouse, Walk to Duval - KAMP
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $1033 per night (USD)
VRBO
From $776 per night (USD)
Expedia
Key West Lighthouse Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape the Ordinary... The Key West Lighthouse Suite offers a cozy queen bungalow home with a unique queen loft and sle ...
From $776 per night (USD)
Expedia
From $1030 per night (USD)
VRBO
American Shoal Light Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape the Ordinary.... The American Shoal Lighthouse Suite offers separate King and Queen bedrooms and was completely ...
From $1030 per night (USD)
VRBO
From $907 per night (USD)
Expedia
Tortugas Harbor Light Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape the Ordinary... The Tortugas Harbor Lighthouse Suite offers a luxury king bedroom that can accommodate up to 4 g ...
From $907 per night (USD)
Expedia
From $907 per night (USD)
VRBO
Sombrero Reef Light Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape the Ordinary... The Sombrero Reef Lighthouse Suite offers a luxury king bedroom that can accommodate up to 4 gue ...
From $907 per night (USD)
VRBO
From $883 per night (USD)
Expedia
Alligator Reef Light Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape the Ordinary... The Alligator Reef Lighthouse Suite offers separate King and Queen bedrooms and was completely r ...
From $883 per night (USD)
Expedia
From $1007 per night (USD)
VRBO
~CALIFORNIA DREAMING~ Enjoy an extended vacation in this posh home and pool.
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $1007 per night (USD)
VRBO
Click For Pricing
Expedia
Studio Unit in quiet resort adjacent to Old Town Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
With a coveted location in the heart of Old Town and magnificent views of the Gulf of Mexico, Sunset Harbor is the ultim ...
Click For Pricing
Expedia
$Escape to \Casa Escondida\$
From $579 per night (USD)
VRBO
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 $579 per night (USD)
VRBO
From $588 per night (USD)
Expedia
**THE COZY STARFISH @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICES…
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE COZY STAR ...
From $588 per night (USD)
Expedia
From $3877 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 $3877 per night (USD)
VRBO
From $1189 per night (USD)
VRBO
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)
VRBO
From $2066 per night (USD)
VRBO
Sunset Harbor Resort & Spa, Hot Tub, Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $2066 per night (USD)
VRBO
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 $695 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 $695 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Beautifully Renovated Paradise with Pool and Tropical Gardens in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step into paradise in this clean and impeccably appointed 2 bedroom, 2 bathroom house in Old Town. Located just 2 blocks ...
From $235 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Old Town main house and guest house one block from Duval Street for the best of Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This luxury Old Town renovation is on a quiet end of Virginia street with no through traffic but located only one block ...
From $284 per night (USD)
VRBO
From $1104 per night (USD)
Expedia
**GARDEN OF EMMA @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Tranquility. ...
From $1104 per night (USD)
Expedia
From $312 per night (USD)
VRBO
Bohemian Retreat with Pool in Old Town Key West | Free Breakfast Onsite!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $312 per night (USD)
VRBO
From $480 per night (USD)
VRBO
Romantic Key West Getaway with Heated Pool, Patio & Breakfast | Near Sunset Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $480 per night (USD)
VRBO
$Escape to \Oasis on 18th\ w/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary!$
From $361 per night (USD)
VRBO
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 $361 per night (USD)
VRBO
From $446 per night (USD)
VRBO
Quaint Bungalow w/ Private Outdoor Space Near Duval Street | Free Breakfast
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 $446 per night (USD)
VRBO
From $528 per night (USD)
VRBO
Celebrate History in Key West: Tropical Free Breakfast and Pool Access!
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 $528 per night (USD)
VRBO
From $433 per night (USD)
VRBO
Serene Bungalow with Outdoor Pool Access | Free Breakfast Onsite!
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 $433 per night (USD)
VRBO
From $483 per night (USD)
VRBO
Romantic Getaway with Plush Turkish Robes & Inviting Pools! Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $483 per night (USD)
VRBO
From $461 per night (USD)
VRBO
Key West Oasis: Retreat in Historical Bungalows with Pool, Free Breakfast!
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 $461 per night (USD)
VRBO
From $482 per night (USD)
VRBO
Serene Bungalow in Key West: Poolside Refreshers & Free Breakfast!
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 $482 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Tranquil Bungalow w/ an Artistic Vibe in Vibrant Key West | Breakfast Included
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 $465 per night (USD)
VRBO
From $439 per night (USD)
VRBO
Stylish Room in the Heart of Old Town w/ Access to Outdoor Pool | Free Breakfast
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 $439 per night (USD)
VRBO
From $519 per night (USD)
VRBO
Historical Charm in a Room Surrounded by Key West's Best: Free Breakfast!
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 $519 per night (USD)
VRBO
From $393 per night (USD)
VRBO
Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $393 per night (USD)
VRBO
From $531 per night (USD)
Expedia
Palms and Pool Paradise
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Welcome to our luxurious Key West retreat in the heart of midtown! This spacious house boasts a private pool, soothing h ...
From $531 per night (USD)
Expedia
$Hemmingways Paradise \nJust a short stroll to all Key West has to offer.$
Click For Pricing
VRBO
Hemmingways Paradise \nJust a short stroll to all Key West has to offer.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
You will fall in love with this beautifully renovated old town historic home. Located on one of old towns coveted quiet ...
Click For Pricing
VRBO
From $2427 per night (USD)
VRBO
4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2427 per night (USD)
VRBO
From $713 per night (USD)
VRBO
One Bedroom Suite Queens, Pier House, Roomy Elegance, Beachside Bliss, Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $713 per night (USD)
VRBO
From $640 per night (USD)
VRBO
Serene Resort Room with Private Beach & Spa - Perfect Key West Escape
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $640 per night (USD)
VRBO
From $989 per night (USD)
VRBO
One Bedroom Suite King, Pier House, Spacious Comfort, Spa Access, Ocean Breeze
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $989 per night (USD)
VRBO
From $937 per night (USD)
VRBO
Oceanfront King, Pier House, Stunning Ocean Views, Plush King Bed, Duval Locale
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $937 per night (USD)
VRBO
From $656 per night (USD)
VRBO
Family-Friendly Key West Resort with Private Beach on Duval St.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $656 per night (USD)
VRBO
From $950 per night (USD)
VRBO
Inviting Key West Paradise Perfect for Couples - Spa & Oceanfront Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $950 per night (USD)
VRBO

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