Key West Rentals
From $143 per night (USD)HomeAway
Feeling Beachy in Key West with fantastic ocean views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully appointed 3rd floor ocean-view condo at the prestigious 1800 Atlantic Complex in Key West. This unit is 1500 ...
From $143 per night (USD)HomeAway
From $300 per night (USD)VRBO
Pelican Landing Harbor Island Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...
From $300 per night (USD)VRBO
From $273 per night (USD)HomeAway
**LA PETITE PENTHOUSE @ THE ANNEX** Elegant Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
LA PETITE PENTHOUSE a jewel-like second-story condo in the Shipyard at the Truman Annex, a gated community located in th ...
From $273 per night (USD)HomeAway
From $414 per night (USD)VRBO
Saltwater Angler @ the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating includin ...
From $414 per night (USD)VRBO
From $343 per night (USD)HomeAway
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
This ultimate Key West dream home is nestled in the highly desirable residential Old Town neighborhood of Solares Hill, ...
From $343 per night (USD)HomeAway
From $125 per night (USD)VRBO
"TORTOISE SHELL II" ~ Comfortable, Modern Condo Two Blocks from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CLASSIC KEY Tortoise Shell II is an elegant two bedroom, 2 bath condominium one block off of famous Duval Street. Secon ...
From $125 per night (USD)VRBO
From $80 per night (USD)HomeAway
Paradise Palm at the Key West Golf Club
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Paradise Palm***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***This is a beautiful, private two-story open plan townhome ba ...
From $80 per night (USD)HomeAway
From $371 per night (USD)VRBO
Four Palms of Casa Marina-Monthly Rental
- Bedrooms:
- 5.5
- Bathrooms:
- 3
- Sleeps:
- 8
WELCOME TO FOUR PALMS! This lovely 2 story home is in the well-respected neighborhood of Casa Marina. The main house ...
From $371 per night (USD)VRBO
From $207 per night (USD)HomeAway
Angler's Retreat @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A stay in Anglers Retreat is more then just a rental, but will be part of your Key West vacation experience. In addition ...
From $207 per night (USD)HomeAway
From $181 per night (USD)VRBO
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home + Private Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
For a month in Key West it is ideal to harness the comforts of new construction similar to the luxuries of your own home ...
From $181 per night (USD)VRBO
From $171 per night (USD)HomeAway
Hemingway's Hammock @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $171 per night (USD)HomeAway
From $382 per night (USD)VRBO
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
Traveling to Key West with a group deserves the ultimate vacation rental home: plenty of space to stretch out and enjoy ...
From $382 per night (USD)VRBO
From $452 per night (USD)HomeAway
**BAHAMIAN BAMBOO @ THE ANNEX** Chic Home By Duval & Beach + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
BAHAMIAN BAMBOO has been painstakingly decorated and furnished in a sophisticated yet distinctive Bahamian style. Your l ...
From $452 per night (USD)HomeAway
From $214 per night (USD)VRBO
Eaton Manor - 2 Bedroom Condo with a Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...
From $214 per night (USD)VRBO
From $414 per night (USD)HomeAway
Paradise on the Ocean @ the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...
From $414 per night (USD)HomeAway
From $165 per night (USD)VRBO
Luxury High End New Reno, Free Bikes, Free Wi-Fi Pool, Hot Tub, Gym, Tennis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly Renovated April 2019 Luxury Executive 1 Bedroom 1 Bathroom located at 1800 Atlantic. It is a Penthouse Unit that ...
From $165 per night (USD)VRBO
From $478 per night (USD)HomeAway
PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO PINEAPPLE COTTAGE! Just a 1/2 block to Duval, parking, and private pool! This two bedroom, two bathroom ho ...
From $478 per night (USD)HomeAway
From $207 per night (USD)VRBO
Dolphin Delight @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $207 per night (USD)VRBO
From $288 per night (USD)HomeAway
Somewhere on the beach: 2 BR, 2 BA Condominium in Key West, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Somewhere on the Beach has Amazing sweeping views of the Atlantic. Watch the sun rise over the Atlantic from the . comf ...
From $288 per night (USD)HomeAway
From $120 per night (USD)VRBO
Enjoy More Privacy in a Truman Annex End Unit Townhome
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
Contact us about special Summer Rates! Absolute Best Location! Our Townhome is set in the tranquil verdant gardens of ...
From $120 per night (USD)VRBO
From $134 per night (USD)HomeAway
@@ Boat House Harbor March 2020 Excellent Monthly fabulous Ocean View @@
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This property has been totally renovated and features a fantastic roll in custom shower which is fully wheelchair access ...
From $134 per night (USD)HomeAway
From $643 per night (USD)VRBO
**CIELO TROPICALE @ CASA MARINA** Estate / Large Pool + LAST KEY SERVICES...
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 10
On a quiet court just a short walk from Old Town and a block from the beach is CIELO TROPICALE, a stunning home complete ...
From $643 per night (USD)VRBO
From $171 per night (USD)HomeAway
Alhambra @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $171 per night (USD)HomeAway
From $171 per night (USD)VRBO
Island Spa @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This Shipyard unit has a Queen bed, one bathroom, very sunny, bright condo.It has a very nice large deck balcony facing ...
From $171 per night (USD)VRBO
From $353 per night (USD)HomeAway
**SUNSET DREAMS @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
SUNSET DREAMS has everything you could want in a vacation home: it is very close to Old Town, so you'll be able to enjoy ...
From $353 per night (USD)HomeAway
From $100 per night (USD)VRBO
30 night Minimum Stay Heart of Historic downtown 232 2 bed 2 1/2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is a luxury town home, located in the heart of old town and walking distance to all main attractions, including th ...
From $100 per night (USD)VRBO
From $218 per night (USD)HomeAway
**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This modernized historic Old Town condo is just right for a delightful stay in the Conch Republic. CASITA ANGELITA is lo ...
From $218 per night (USD)HomeAway
From $288 per night (USD)VRBO
@@ Totally Renovated Ocean View Condo Great Prices @@
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Atlantic Paradise Found C232 at 1800 Atlantic Condominiums is a beautifully appointed spacious condominium with a lovely ...
From $288 per night (USD)VRBO
From $288 per night (USD)HomeAway
Flip flops in Cayo Hueso A305: 2 BR, 2 BA Condominium in Key West, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stunning 2 bedroom ocean-view oasis vacation rental at the fabulous 1800 Atlantic in Key West. Our family owned unit has ...
From $288 per night (USD)HomeAway
From $382 per night (USD)VRBO
**BANANA BLOSSOMS @ THE ANNEX** Lush Villa by Beach + Pool + LAST KEY SERVICES
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
When exploring Old Town Key West it is typical to stumble upon a surprise tropical bloom that reminds you of the magic o ...
From $382 per night (USD)VRBO
From $200 per night (USD)HomeAway
Tropical Meadows Bungalow!! Private hot tub!! Shared pool!! Great Location!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Great location on White street in Old Town! Bike rentals a block away and Duval street a few blocks away! Historic hom ...
From $200 per night (USD)HomeAway
From $179 per night (USD)VRBO
"CARIBBEAN SOUL" ~ 3 Bedroom, 3.5 Bath , Sleeps 6, Private Pool & Parking!
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 6
QUINTESSENTIAL KEY WEST HOME LEAVING NOTHING MORE TO BE DESIRED... Framed by a white picket fence you will be welcomed t ...
From $179 per night (USD)VRBO
From $50 per night (USD)HomeAway
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 $50 per night (USD)HomeAway
From $75 per night (USD)VRBO
Boli Townhouse - Luxury Rental in Key West - Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Boli Townhouse is located in the Truman Annex, a gated community in downtown old Key West. The Boli Townhouse is a two b ...
From $75 per night (USD)VRBO
From $414 per night (USD)HomeAway
Tropical Executive @ the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $414 per night (USD)HomeAway
From $218 per night (USD)VRBO
**SEAPORT SENSATION @ THE SEAPORT** Elegant Living 1 Block off Duval + Pool + LAST KEY SERVICES…
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
It is not so often that something new is built in Old Town, the historic district of Key West known for quintessential c ...
From $218 per night (USD)VRBO
From $571 per night (USD)HomeAway
Admiral's Gold @ the Truman Annex
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful vacation home in Key West in the award-winning Truman Annex, this 3 story, 4 bedroom 3.5 bath townhome sits on ...
From $571 per night (USD)HomeAway
From $207 per night (USD)VRBO
Island Breezes @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This charming second floor condominium features two bedrooms, and one full bath with views of the Truman Waterfront Park ...
From $207 per night (USD)VRBO
From $209 per night (USD)HomeAway
Flip Flop Retreat Townhome in Quiet Convenient Location
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
Two bedroom, 2.5 bath townhome in Truman Annex two blocks to Duval Street. Quiet, clean, comfortable oasis in perfect l ...
From $209 per night (USD)HomeAway
From $59 per night (USD)VRBO
Lock-Out Unit at the Galleon Resort - Best Resort Location In KW
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio(lock-out) for rent 5th floor. The Galleon Resort has its own marina, fishing charters on-site, tiki bar that serv ...
From $59 per night (USD)VRBO
From $584 per night (USD)HomeAway
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
For many, the artistic island culture of Key West is an intricate piece of its magic. THE ARTISTS' MUSE is an ode to tha ...
From $584 per night (USD)HomeAway
From $900 per night (USD)VRBO
Admiral's Treasure @ the Truman Annex
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
When you are seeking one of the best large home accommodations, look no further....you have found Admirals Treasure, a f ...
From $900 per night (USD)VRBO
From $329 per night (USD)HomeAway
Absolute Key West @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This Private home is located in the historic Truman Annex of old town Key West, where you can get away from it all while ...
From $329 per night (USD)HomeAway
From $207 per night (USD)VRBO
Cabana Breeze @ 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 $207 per night (USD)VRBO
From $100 per night (USD)HomeAway
Oceanfront
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the charm and grace of Old Key West in a new and distinctive setting. Luxury, two-bedroom, two-bath, waterfront ...
From $100 per night (USD)HomeAway
From $400 per night (USD)VRBO
Key West Paradise in Old Town Neighborhood and close to everything
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 6
THE HOME… A beautiful two and a half story private home with a refreshing mix of classic Key West and classy coastal. ...
From $400 per night (USD)VRBO
From $223 per night (USD)HomeAway
All Decked Out @ The Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is a monthly rental only. IMMACULATE RETREAT STEPS FROM IT ALL...Beautifully designed and decorated townhouse loca ...
From $223 per night (USD)HomeAway
From $239 per night (USD)VRBO
Key West Home/Pool on the Water
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
BOAT LOVERS! Five minutes to open ocean. Keep your boat in the canal right at your back door. KAYAK LOVERS! Slip the ...
From $239 per night (USD)VRBO
From $300 per night (USD)HomeAway
BMW Fantasy - 2 Bedroom 2 1/2 Bathroom Condo with a Shared Pool
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Downtown Duval St. 2 bedroom 2 1/2 bath condo, located in the heart of Old Town. Walking distance to many of the main at ...
From $300 per night (USD)HomeAway
From $763 per night (USD)VRBO
**THE COMMODORE'S MANOR @ PARADISE HARBOR** Waterfront Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
THE COMMODORE'S MANOR is a beautiful 5 bedroom 3500 sq ft town home that is located directly on the water at Garrison Bi ...
From $763 per night (USD)VRBO
From $234 per night (USD)HomeAway
Key West Suites Hotel #201 on Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel #201 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it u ...
From $234 per night (USD)HomeAway
From $350 per night (USD)VRBO
Galleon Resort Waterfront Luxury in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $350 per night (USD)VRBO
From $134 per night (USD)HomeAway
Aquamarine Delight on the Ocean C333: 2 BR, 2 BA Condominium in Key West, Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy ocean views from this bright and airy 3rd floor unit. This newly renovated unit comes fully equipped with attenti ...
From $134 per night (USD)HomeAway
From $770 per night (USD)VRBO
Queen Emma @ the Truman Annex*
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautifully finished and decorated four bedroom, three bath home has classic Key West architecture and is located o ...
From $770 per night (USD)VRBO
From $107 per night (USD)HomeAway
"VILLAGE ROOSTER" ~ Quaint Cottage in Bahama Village Steps from the FUN!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
BAHAMA VILLAGE TREASURE... This pet friendly Old Town Key West home is just steps from the award winning restaurants and ...
From $107 per night (USD)HomeAway
From $214 per night (USD)VRBO
Shipyard 253 - 2 Bedroom Condo with a Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
7 night minimum stay condo upstairs unit with 2 bedrooms and 1 Bathroom upstairs spacious unit with 1 queen, 2 twins and ...
From $214 per night (USD)VRBO
From $177 per night (USD)HomeAway
**SUNSET REVERIE @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SUNSET REVERIE is located in Sunset Marina, a gated community located on Stock Island right off the entrance to Key West ...
From $177 per night (USD)HomeAway
From $429 per night (USD)VRBO
Blue Lagoon @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This cheery property located on Southard Street features three bedrooms, one on the first level and two on on the second ...
From $429 per night (USD)VRBO
From $236 per night (USD)HomeAway
Poolside Hangover @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and close to a ...
From $236 per night (USD)HomeAway
From $207 per night (USD)VRBO
Starshine Key West @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $207 per night (USD)VRBO
From $273 per night (USD)HomeAway
**EDEN @ THE ANNEX** Old Town Villa & Pool by Duval + LAST KEY SERVICES...
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
EDEN @ THE ANNEX is a charming townhome in Truman Annex, a gated community located in the very heart of Old Town Key Wes ...
From $273 per night (USD)HomeAway
From $89 per night (USD)VRBO
"PINEAPPLE COTTAGE" ~ Adorable, Updated Cottage in Old Town with Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RELAXED DOWNTOWN LIVING... Envelop yourself in true island living in this cute cottage just for the two of you. Located ...
From $89 per night (USD)VRBO
From $414 per night (USD)HomeAway
Worlds End @ the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $414 per night (USD)HomeAway
From $300 per night (USD)VRBO
Latitude Adjustment @ the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renov ...
From $300 per night (USD)VRBO
From $207 per night (USD)HomeAway
Charming, first floor end unit! GREAT LOCATION!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Low Tide is a charming first floor end unit in the Shipyard Condominiums in the award wining gated community of the Trum ...
From $207 per night (USD)HomeAway
From $279 per night (USD)VRBO
Captains Wheel @ the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
This very popular getaway in the award-winning Truman Annex is a tropically decorated 2 bedroom, 2.5 bath town home feat ...
From $279 per night (USD)VRBO
From $20 per night (USD)HomeAway
KEY WEST FANTASY FEST WEEK OCT. 16-23, 2021
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West, FL. Available Sat. Oct.19 - Sat. 26, 2019. Located in the Southeast end of Key West at the Hyatt Windward Poin ...
From $20 per night (USD)HomeAway
From $171 per night (USD)VRBO
Sun, Sea and Sky @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sun Sea and Sky is only two blocks from bustling Duval Street, the heart of Old Town Key West, with an easy walk to rest ...
From $171 per night (USD)VRBO
From $228 per night (USD)HomeAway
Tropical Jewel in Historic Seaport - 2BR/2BA - Pool - Monthly Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WELCOME TO TROPICAL JEWEL! Imagine yourself staying in this immaculate restored home just two blocks away from the H ...
From $228 per night (USD)HomeAway
From $161 per night (USD)VRBO
@March 2020 $7750 plus fees Anglers Retreat open @@
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our paradise please enjoy our modern 1400 square foot 2 bedroom 2 bathroom totally renovated condo. This cond ...
From $161 per night (USD)VRBO
From $171 per night (USD)HomeAway
Royal Poinciana @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $171 per night (USD)HomeAway
From $214 per night (USD)VRBO
Paradise Found 2 Bedroom Condo with a Shared Pool Completely Renovated
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Completely renovated, 7 night minimum rental. This condo has everything you want and more. Paradise is definitely found ...
From $214 per night (USD)VRBO
From $100 per night (USD)HomeAway
Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This lovely Island Escape Condo is a upper level condo located in the Truman Annex Shipyard a luxury gated community. No ...
From $100 per night (USD)HomeAway
From $714 per night (USD)VRBO
Treehouse Island @ The Truman Annex
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Treehouse Island is a traditional Key West eyebrow house. Inside it's spacious and up-to-date, yet as comfortable as you ...
From $714 per night (USD)VRBO
From $218 per night (USD)HomeAway
**SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Formerly La Bonne Vie, SMOOTH SAILING has been meticulously furnished with a modern coastal feel, and the only beauty th ...
From $218 per night (USD)HomeAway
From $274 per night (USD)VRBO
NEWLY RENOVATED ...LAST MINUTE SPECIALS...CHECK DATES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
THIS IS DREAM MAKER...THE ONE YOU HAVE BEEN SEARCHING FOR Let us help make your dreams come true: Enjoy your tranquil ...
From $274 per night (USD)VRBO
From $436 per night (USD)HomeAway
**GULFSIDE VISTAS @ THE ANNEX** Ocean Penthouse & Pool + LAST KEY SERVICE...
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
GULFSIDE VISTAS is a beautiful penthouse condo and is the perfect place to spend your stay in Key West, with panoramic v ...
From $436 per night (USD)HomeAway
From $389 per night (USD)VRBO
**LA VIE EN ROSE @ BEACHSIDE** Modern Home / Large Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
LA VIE EN ROSE is a classic mid-century modern home set in the Beachside district of Key West, just a couple blocks from ...
From $389 per night (USD)VRBO
From $50 per night (USD)HomeAway
DESIGN YOUR OWN WATER ADVENTURE
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
A well appointed and renovated 36' Morgan Out Island Sloop, at ANCHOR with no dock, north of KW harbor . 2 guest MAXIMUM ...
From $50 per night (USD)HomeAway
From $279 per night (USD)VRBO
Sago Palm @ the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $279 per night (USD)VRBO
From $250 per night (USD)HomeAway
Oceanview home with expansive decks and private pool in lush landscaping
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
"Banana Breeze" is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasi ...
From $250 per night (USD)HomeAway
From $357 per night (USD)VRBO
Oceanfront, Resort-like luxury home with private pool & lush landscaping
- 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 $357 per night (USD)VRBO
From $294 per night (USD)HomeAway
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
A stay in Key West calls for a light and airy oasis, with breathtaking water views and an easy beach location to fully e ...
From $294 per night (USD)HomeAway
From $134 per night (USD)VRBO
@ Reserve Morning Reflections for Monthly rent May - September 2020@
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen wit ...
From $134 per night (USD)VRBO
From $714 per night (USD)HomeAway
Dolphin Watch @ the Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
RECENTLY UPDATED & VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to ...
From $714 per night (USD)HomeAway
From $124 per night (USD)VRBO
Quiet, elegant, Key West Condo close to the Ocean
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all ...
From $124 per night (USD)VRBO
From $300 per night (USD)HomeAway
Blu on White · New to the Market! 4 Bed, 3 Bath-Old town w/ Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
NEW ON THE RENTAL MARKET This recently renovated four bedroom, three bathroom traditional shotgun house with a twist, ha ...
From $300 per night (USD)HomeAway
From $143 per night (USD)VRBO
Starrs Atlantic Oasis C138: 2 BR, 2 BA Condominium in Key West, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a ...
From $143 per night (USD)VRBO
From $279 per night (USD)HomeAway
Fun in the Sun @ the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
This stately 2 bedroom townhouse in the President's Walk area of Porter Lane is furnished with tropical and luxury decor ...
From $279 per night (USD)HomeAway
From $256 per night (USD)VRBO
**VIVA MARGARITA! @ OLD TOWN** Large Home & Pool Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 5.5
- Bathrooms:
- 3
- Sleeps:
- 8
Key West is the mecca for those seeking to live life the way it is supposed to be lived: in the sunshine with a cold dri ...
From $256 per night (USD)VRBO
From $300 per night (USD)HomeAway
Pelican Landing Dominica Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...
From $300 per night (USD)HomeAway
From $566 per night (USD)VRBO
**LA GRANDE REUNION @ OLD TOWN** Estate & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 10
Traveling with a large group requires a special home. To maximize comfort, large common areas are offered both indoor an ...
From $566 per night (USD)VRBO
From $273 per night (USD)HomeAway
**VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES...
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
VILLA BAHAMA is located at The Foundry in the Truman Annex, Key West's most exclusive gated community. You'll be just ar ...
From $273 per night (USD)HomeAway
From $300 per night (USD)VRBO
Pelican Landing Abaco Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...
From $300 per night (USD)VRBO
From $279 per night (USD)HomeAway
A Southern Conch Cottage @ the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
A Southern Conch Cottage is tucked away at the end of quiet Porter Lane in the award-winning gated community of the Trum ...
From $279 per night (USD)HomeAway
From $288 per night (USD)VRBO
Smathers Retreat on the Atlantic C239: 2 BR, 2 BA Condominium in Key West, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Spectacular 2 bedroom 2 bath ocean-view overlooking the famous Smathers Beach, Enjoy the balmy ocean breezes from your ...
From $288 per night (USD)VRBO
From $872 per night (USD)HomeAway
**STAR OF THE SEAPORT @ THE HISTORIC SEAPORT** Prime Location & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
For a truly over-the-top Key West stay with your entire group, whether that be the whole family or your closest friends, ...
From $872 per night (USD)HomeAway
From $491 per night (USD)VRBO
**SWEET HOME ANGELITA @ OLD TOWN** Renovated Home Off Duval + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
This renovated Old Town estate is designed for the real downtown experience in the Conch Republic, but in a large home-b ...
From $491 per night (USD)VRBO
From $215 per night (USD)TripAdvisor
Tropical Escape
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a ...
From $215 per night (USD)TripAdvisor
From $175 per night (USD)PerfectPlaces
Conch Adventure
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in a quiet corner of the Shipyard section in the desirable Truman Annex, this 2-bedroom 1 bath downstairs condo ...
From $175 per night (USD)PerfectPlaces