- Meadows
- Oceanside Marina (formerly Kings Pointe)
- Private Homes, DownTown
- Private Homes, Historic Seaport
- Private Homes, Mid Town
- Private Homes, New Town
- Private Homes, Old Town
- Private Homes, Unspecified
- Private Homes, UpTown
- Seaside Resort
- Sunrise Suites
- Sunset Marina
- Truman Annex
- Villas Key West
- White St. Gallery
- Windward Park
- 1800 Atlantic
- Bahama Village
This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
-
Key West Vacation Rentals Show this location only Back to top
- Affordable, Charming, Quiet, Walking Distance to Town, Shopping, Dining, Beach 1BR/1BA – Sleeps 3 – Truman Annex #299544ha
- Charming Yacht Located in Exclusive, Beautiful Key West Harbour Yacht Club 2BR/1BA – Sleeps 4 – Other Key West Properties #968728ha
-
Private House: a Peaceful Oasis, Monthly Rental Only
4BR/3BA
–
Sleeps 8
– Other Key West Properties #173113ha
$15000 per month 30 night min stay
-
Rose Lane Villa's Villa Alta 1 BR -- Quiet and Just Steps to Duval!
1BR/1BA
–
Sleeps 4
– Other Key West Properties #243695ha
$169 - $379 per night
-
Top-Floor Smathers Beach Condo with Gorgeous Pool, Tennis and Steps from Beach.
2BR/2BA
–
Sleeps 4
– Other Key West Properties #254856ha
$150 - $350 per night
- Key West Oceanfront Condo - 'the Sea Jay' 2BR/2BA – Sleeps 6 – Other Key West Properties #134883ha
-
Treehouse Island: Private Home with Pool & Internet, Walk to Key West Hot Spots!
3BR+/4BA
–
Sleeps 8
– Truman Annex #3013423ha
$4500 - $6500 per week
- Luxurious Ocean Front Oasis in Key West 3BR/2BA – Sleeps 6 – Other Key West Properties #257495ha
-
Attitude Key West at the Beach
1BR/1BA
–
Sleeps 4
– Other Key West Properties #994355ha
$275 per night 3 night min stay
-
Modern Home with Great Location - Room for Whole Family - Including Pets
3BR/1BA
–
Sleeps 6
– Other Key West Properties #938871ha
$83 - $133 per night
-
'Cielo Tropicale @ Casa Marina' Lush & Spacious 4BR/4BA Estate + Large Pool...
4BR/4BA
–
Sleeps 8
– Other Key West Properties #3015071ha
$13000 - $22000 per month 28 night min stay
- Still a Few Feb Weeks,,,Ck Today !!!! 2BR/1BA – Sleeps 6 – Other Key West Properties #212518ha
-
Rose Lane Villa's Villa Porta 1 Bedroom, 1/2 Block Off Duval
1BR+/1BA
–
Sleeps 4
– Other Key West Properties #299236ha
$159 - $369 per night
-
True Key West Experience! Coastal Living's Artists Paradise!
Studio/0BA
–
Sleeps 6
– Private Homes, Old Town #384490
$4500 per month
- Petronia Palms for Budget Minded by Duval St Has a Large Pool! Studio/1BA – Sleeps 2 – Other Key West Properties #258192ha
-
Nassau Suite - Old Town Key West Villa 1BR/1BA – Sleeps 4 – Other Key West Properties #390414ha
Special offer Sizzling Summer Special
Jun 14, 2013 to Oct 20, 2013
$185 - $285 per night 3-7 night min stay - Oceanfront 2BR/2BA – Sleeps 6 – Other Key West Properties #162417ha
-
Charming Cottage Located on Quiet Walking Lane
2BR+/1BA
–
Sleeps 5
– Truman Annex #389177ha
$1400 per week 7 night min stay
- Key West Luxury Art Deco Style Oceanside Condo with Pool and Beach 2BR/2BA – Sleeps 6 – Other Key West Properties #255720ha
-
Beautiful Truman Annex Townhome Near the Pool!
2BR/2BA
–
Sleeps 4
– Truman Annex #359528ha
$1800 - $2600 per week
-
Rose Lane Villa's 'Villa Rosa' 1 Bedroom, 1/2 Block Off Duval
1BR/1BA
–
Sleeps 4
– Other Key West Properties #299233ha
$159 - $369 per night
-
Key West - Truman Annex Cottage-Best Location on the Island-Newly Renovated!
2BR/2BA
–
Sleeps 5
– Truman Annex #273217ha
$2750 per week
-
Casa Colonial Island Luxury in Key West
4BR/3BA
–
Sleeps 7
– Other Key West Properties #329361ha
$5200 - $5800 per week
-
Enjoy an Authentic Key West Experience
2BR/2BA
–
Sleeps 4
– Private Homes, Old Town #282583ha
$3500 - $5500 per month
-
Sunkissed Vision: Key West Condo Near Beach & Old Town-Fabulous Dining!
3BR/2BA
–
Sleeps 7
– Truman Annex #3012153ha
$4950 per week
-
Sweet Spot for Two…Everything You Need for an Enchanted Tropical Get-Away.
Studio/0BA
–
Sleeps 2
– Other Key West Properties #3002580ha
$136 - $214 per night
- Key West Rental (Casa De Suenos) House of Dreams! 1BR+/1BA – Sleeps 4 – Other Key West Properties #182589ha
-
Old Town Key West 2 Bedroom Cottage with Private Pool
2BR/2BA
–
Sleeps 6
– Truman Annex #390412ha
$4500 - $7500 per month 30 night min stay
-
Paradise in Old Town!!!
2BR/2BA
–
Sleeps 6
– Other Key West Properties #3478179ha
$4480 - $5500 per month
-
Charming Queen Conch Cottage - 2 Blocks to Duval Street!
2BR/1BA
–
Sleeps 6
– Other Key West Properties #3013405ha
$17143 per month
-
Duval Street Luxury Home with Private Pool-Perfect for Family Reunions
5BR/4BA
–
Sleeps 10
– Other Key West Properties #3013408ha
$1500 per night
-
Key Haven Elegance
4BR/1BA
–
Sleeps 10
– Other Key West Properties #3013415ha
$7000 per week
-
Pet Friendly Cottage
Studio/1BA
–
Sleeps 4
– Other Key West Properties #391123ha
$148 - $168 per night 2-3 night min stay
-
Key West Hideaway
3BR/3BA
–
Sleeps 10
– Other Key West Properties #391134ha
$5000 - $7500 per month 30 night min stay
- Southernmost Escape - a Classic Key West Style Townhome with Extras 3BR/3BA – Sleeps 6 – Other Key West Properties #3012211ha
-
Southernmost Oasis: Bbq Grill, Jacuzzi, Heated Pool with Waterfall
3BR/2BA
–
Sleeps 6
– Other Key West Properties #3012231ha
$11500 per month
-
Old Town Beauty - Charming Home 2 Blocks from Beach!
3BR/2BA
–
Sleeps 6
– Other Key West Properties #3012142ha
$19286 per month
-
Old Town Oasis
4BR/3BA
–
Sleeps 8
– Other Key West Properties #3013409ha
$34286 per month
-
Oceanview Spectacular: Enjoy Sunsets from 3BR Penthouse W/ Pool
3BR/3BA
–
Sleeps 6
– Other Key West Properties #3012154ha
$4950 per week
-
Sweet Disposition
3BR/2BA
–
Sleeps 8
– Other Key West Properties #3013421ha
$5000 per week
- Coconut Cabana: Private Home with Wifi and Pool - Excellent Location! 3BR+/2BA – Sleeps 8 – Other Key West Properties #3013461ha
-
Villa Key West
6BR/6BA
–
Sleeps 14
– Other Key West Properties #3012182ha
$60000 per month
-
Archipelago
4BR/4.5BA
–
Sleeps 12
– Truman Annex #3013413ha
$3500 - $5500 per week
- Private Poolside Paradise 3BR/3BA – Sleeps 8 – Truman Annex #3013424ha
- Casa Key West 3BR/3BA – Sleeps 8 – Truman Annex #3013437ha
-
Calypso Dreams- Patio with Bbq Grill, Private Pool, Wifi, Guest House!
5BR/5BA
–
Sleeps 12
– Truman Annex #3012148ha
$9000 per week
-
Tropical Temptations: Fabulous Sunsets, Gourmet Kitchen, Harbor View!
4BR/3BA
–
Sleeps 8
– Other Key West Properties #3012157ha
$3500 - $5500 per week
-
Slice of Eden: Luxurious Waterfront 4BR in Key West W/ Private Pool
4BR/2BA
–
Sleeps 8
– Truman Annex #3012170ha
$4500 - $6500 per week
-
Key West Embrace: Charming Condo with Pool and Gorgeous Water Views
4BR/3BA
–
Sleeps 8
– Truman Annex #3012173ha
$4004 - $4102 per week
-
Admirals Private Retreat: Tropical Pool Home 2 Blocks from Duval Street!
3BR/3BA
–
Sleeps 6
– Truman Annex #3012213ha
$6500 per week
-
The Cristol Condo - Classic Key West Oceanfront Charm
4BR/4BA
–
Sleeps 8
– Truman Annex #3177514ha
$4989 per week
- Tropical Reatreat! 4BR/3BA – Sleeps 8 – Other Key West Properties #207517ha
-
Quiet Waterfront Condo with Boat Slip, Beach and Pool! One of a Kind!
2BR/2BA
–
Sleeps 4
– Other Key West Properties #335989ha
$3500 - $4500 per month
- Charming, Quiet, Old Town, Walking Distance to Everything 1BR+/1BA – Sleeps 4 – Other Key West Properties #369947ha
-
Casa Mara is an Adorable Cottage on a Small Quiet Lane in Old Town
2BR/2BA
–
Sleeps 4
– Other Key West Properties #3471712ha
$4500 - $5320 per month 28 night min stay
-
Island Oasis
3BR/2BA
–
Sleeps 6
– Truman Annex #391120ha
$368 - $468 per night 3-5 night min stay
-
Downtown Key West Pool Home
2BR/2BA
–
Sleeps 6
– Key West Harbour Yacht Club #391125ha
$368 - $408 per night 3-5 night min stay
-
Charming Caretaker's Apartment in Old Town
1BR/1BA
–
Sleeps 4
– Other Key West Properties #359005ha
$145 - $165 per night
-
Cute Cottage with Pool - Perfect Location - Minutes to the Beach!
2BR/2BA
–
Sleeps 4
– Other Key West Properties #395077ha
$3500 - $7501 per month 28 night min stay
-
Old Town Compound: Historic Captain’S House W/Screened Porch & Cottage
5BR/4BA
–
Sleeps 14
– Other Key West Properties #3012214ha
$920 per night
- Tropical Serenity: Home Near Old Town Key West Attractions & Beaches 3BR+/2BA – Sleeps 8 – Truman Annex #3012156ha
-
Treasure of the Tropics: 4BR/4BA W/ Pool & Rooftop Terrace in Key West
4BR/4BA
–
Sleeps 8
– Truman Annex #3012172ha
$5900 - $7900 per week
-
Absolutely Paradise
3BR/2BA
–
Sleeps 6
– Other Key West Properties #391126ha
$428 - $528 per night 3-5 night min stay
- Old Town Truman & Duval Townhome 2BR/2BA – Sleeps 4 – Other Key West Properties #320640ha
-
Treetop Island Treasure, Palm Isle, Just Off Duval
Studio/1BA
–
Sleeps 4
– Other Key West Properties #391121ha
$168 - $248 per night 2-3 night min stay
-
Oceanside Condo
2BR/2BA
–
Sleeps 4
– Other Key West Properties #956954ha
$200 - $325 per night 2-3 night min stay
-
Tropical Retreat
2BR/1BA
–
Sleeps 4
– Truman Annex #391129ha
$198 - $278 per night 3-5 night min stay
-
Southern Cross
2BR/2BA
–
Sleeps 6
– Other Key West Properties #391128ha
$258 - $308 per night 3-5 night min stay
-
Tropical Village Cottage
2BR/2BA
–
Sleeps 5
– Other Key West Properties #391130ha
$245 - $295 per night 3-5 night min stay
-
Toon Hall
3BR/2BA
–
Sleeps 10
– Other Key West Properties #391131ha
$348 - $448 per night 4-5 night min stay
-
Poolside Paradise
1BR/1BA
–
Sleeps 2
– Other Key West Properties #391127ha
$138 - $168 per night 3-5 night min stay
-
Canal-Front Home with Ocean Access in Beautiful Key West, Florida
4BR/0BA
–
Sleeps 10
– Other Key West Properties #3005929ha
$2333 - $2800 per week
-
Key West Cottage: Bahama House, Key West, Fl, 33040
2BR/2BA
–
Sleeps 6
– Other Key West Properties #391132ha
$298 - $388 per night 3-5 night min stay
-
Luxury Monthly or Seasonal
3BR/2BA
–
Sleeps 6
– Other Key West Properties #332855ha
$167 - $433 per night
-
Summerland Sunsets - Oceanfront Home with Pool & Outdoor Tiki Shower!
4BR/3BA
–
Sleeps 10
– Other Key West Properties #3011882ha
$19286 per month
- Sunset Grace: Pet Friendly Townhome - 2 Blocks from Duval Street! 3BR+/2BA – Sleeps 8 – Truman Annex #3013453ha
-
Private Paradise: Old Town Key West Home in Truman Annex with Heated Pool
4BR/4BA
–
Sleeps 8
– Truman Annex #3012171ha
$6000 - $7500 per week
-
Gorgeous Waterfront Townhome, Bring Your Boat!
3BR/1BA
–
Sleeps 6
– Other Key West Properties #343165ha
$3465 - $4515 per week
-
Cole's Cottage - Quaint & Modern on Quiet Old Town Lane
2BR/1BA
–
Sleeps 3
– Other Key West Properties #251672ha
$3500 - $4500 per month
-
Perfect Old Town Getaway
3BR/3BA
–
Sleeps 6
– Private Homes, Old Town #395078ha
$4500 - $9000 per month
-
Rose Lane Villa's Villa Vista 1 Bedroom, 1/2 Block Off Duval
1BR/1BA
–
Sleeps 4
– Other Key West Properties #299234ha
$159 - $369 per night
-
Cozy Cottage for Two
1BR/1BA
–
Sleeps 1-2
– Private Homes, Old Town #914435ha
$4500 per month
-
Premiere Old Town Home
4BR/2BA
–
Sleeps 10
– Private Homes, Old Town #395082ha
$6000 - $9500 per month
- Key West Paradise Cottages 3BR/3BA – Sleeps 8 – Other Key West Properties #3513504ha
-
Affordable Retreat in Old Town!
2BR/2BA
–
Sleeps 4
– Private Homes, Old Town #368346ha
$3500 - $4500 per month
- One of a Kind Luxury Home - Admirals Treasure 4BR/4BA – Sleeps 8 – Truman Annex #910431ha
- Casa Key West 3BR/2BA – Sleeps 8 – Truman Annex #3513503ha
-
Dock 80'Heated Pool Deep Channel Tennis 15 Min Key West
2BR/1BA
–
Sleeps 4-6
– Other Key West Properties #3567100ha
$114 - $171 per night 5-7 night min stay
-
185 a Day Stay Above the Sea 3BR/3BA Cool a/C Full Kitchen Large Livingroom
3BR/3BA
–
Sleeps 6
– Other Key West Properties #392751ha
$185 per night 2 night min stay
-
Family-Friendly Luxury Home for the Discriminate Traveler
5BR/4BA
–
Sleeps 10
– Other Key West Properties #3523713ha
$20000 - $51429 per month 7-30 night min stay
- Charming Key West Townhome with All the Comforts of Home. 2BR/2BA – Sleeps 6 – Truman Annex #342727ha
-
Casa Marina Elegance! Beautiful!
4BR/4BA
–
Sleeps 8
– Casa Marina #387546ha
$5500 - $8500 per month
-
Key West by the Sea
1BR/1BA
–
Sleeps 1-2
– Other Key West Properties #395081ha
$4000 - $6500 per month
- Waterfront Views from Dolphin Watch 4BR/3BA – Sleeps 8 – Truman Annex #908577ha
-
Love Lane Luxury: Stunning Home with Pool - 2 Blocks to Center of Duval Street
4BR/3BA
–
Sleeps 8
– Other Key West Properties #3013412ha
$51429 per month
- Southernmost Harmony 3BR/2BA – Sleeps 8 – Other Key West Properties #3013428ha
-
Luxury Waterfront Key West Resort Home with Pool and Jacuzzi
3BR/2BA
–
Sleeps 6
– Other Key West Properties #3526517ha
$500 - $600 per night 3 night min stay
-
'Maison Sur La Mer' / Private Enclave with Pool
4BR/3BA
–
Sleeps 8-10
– Other Key West Properties #3513544ha
$15000 - $20000 per month
-
Sunset Lake@Key West Golf Club 3BR/3fullba ~ 2 Master Suites
3BR/3BA
–
Sleeps 6
– Other Key West Properties #3518032ha
$90 - $173 per night
- Palm Court is Located in Historic Old Town Key West, Just Two Blocks from Duval 1BR+/1BA – Sleeps 2 – Other Key West Properties #385057ha