Key West Vacation Rentals and Vacation Home Rentals

Key West Vacation Rental Getaways

Featured Properties

Bali Hideaway

Key West

Cottage

1 BR/ 1 BA

Sleeps 2
Tropical Dreaming

Key West

Home

2 BR/ 3 BA

Sleeps 6
Colony Poolside

Key West

Condo

1 BR/ 1 BA

Sleeps 2

Results 51 - 75 of 212

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More Photos Tropical Dreaming Key West TROPICAL DREAMING -- This tropical 2-bedroom home has been professionally decorated and furnished. ... Details \| Contact Manager	Home	2 / 3 / 6	$340 - $682 Per Night $2100 - $4350 Per Week
More Photos Southard Sophistication Key West 30 DAY MINIMUM RENTAL This amazing restoration of a majestic Key West bungalow is incredible. Mo... Details \| Contact Manager	Home	2 / 2 / 4	Contact Owner Directly For Rates
More Photos Beach Club #204 Key West Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes coo... Details \| Contact Manager	Condo	2 / 2 / 4	$270 - $400 Per Night $1820 - $2730 Per Week
More Photos Southernmost Dacha Key West 30 DAY MINIMUM RENTAL A spacious ground floor one bedroom in a four unit condominium building in the... Details \| Contact Manager	Condo	1 / 1 / 2	Contact Owner Directly For Rates
May 2 - Jun 29 * ... AND THE LIVIN' IS EASY...* Easy Livin', o ...
More Photos Easy Livin' Key West EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cu... Details \| Contact Manager	Home	3 / 4 / 8	$4000 - $9200 Per Week
May 2 - Jun 29 >> Book Paradise Place today for an incredible $850 ...
More Photos Paradise Place Key West PARADISE PLACE – is a ground level one bedroom one bath condominium located in the Palm Gardens comm... Details \| Contact Manager	Condo	1 / 1 / 4	$155 - $333 Per Night $900 - $2030 Per Week
More Photos Beach Club #201 Key West Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes coo... Details \| Contact Manager	Condo	2 / 2 / 4	$270 - $400 Per Night $1820 - $2730 Per Week
More Photos Beach House Condo Key West BEACH HOUSE CONDO: A beautiful 2 bedroom 2 bath ground level condo located in the gated Shipyard Co... Details \| Contact Manager	Condo	2 / 2 / 4	$1300 - $2791 Per Week
More Photos Key West Charming Key West KEY WEST CHARMING at the Shipyard Condominiums. This downstairs 2 bedroom 1 bath home has been lovi... Details \| Contact Manager	Condo	2 / 1 / 4	$1100 - $2538 Per Week
More Photos Lavender Jungle Key West LAVENDER JUNGLE - Beautiful 2 bedroom 1 bath downstairs Shipyard condo located in Truman Annex, thi... Details \| Contact Manager	Condo	2 / 1 / 4	$1100 - $2538 Per Week
May 2 - Jun 29 * A JEWEL OF A SUMMER DEAL * Enjoy the comfort ...
More Photos Crowner's Jewel Key West CROWNER'S JEWEL: Experience the finest in Key West living when you stay in this delightful 2 bedro... Details \| Contact Manager	Condo	2 / 3 / 6	$1500 - $3154 Per Week
More Photos Beach Club #303 Key West Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes coo... Details \| Contact Manager	Condo	2 / 2 / 4	$270 - $400 Per Night $1820 - $2730 Per Week
More Photos Key West Crown Jewel Key West KEY WEST CROWN JEWEL -- We know that you will enjoy staying in our little bit of Paradise. This is ... Details \| Contact Manager	Condo	2 / 2 / 6	$345 - $531 Per Night $2145 - $3369 Per Week
More Photos Packer Retreat Key West 30 DAY MINIMUM RENTAL Packer Retreat is a beautifully renovated "Conch" house with many architectur... Details \| Contact Manager	Home	3 / 3.5 / 6	Contact Owner Directly For Rates
More Photos La Brisa #408E Artists Haven Key West 30 DAY MINIMUM RENTAL La Brisa beach condominiums offer a Florida charm that is relaxing, easy a... Details \| Contact Manager	Condo	3 / 2 / 6	Contact Owner Directly For Rates
More Photos Island Spice Key West ISLAND SPICE -- A lovely 2 bedroom, 2.5 bath townhome, located in the historic Foundry building of t... Details \| Contact Manager	Condo	2 / 3 / 6	$1600 - $3408 Per Week
More Photos La Brisa #304W Egrets Landing Key West 30 DAY MINIMUM RENTAL La Brisa beach condominiums offer a Florida charm that is relaxing, easy a... Details \| Contact Manager	Condo	2 / 2 / 4	Contact Owner Directly For Rates
More Photos Townhomes on Windsor #4 Key West Elegance and modern sophistication are apparent as you enter any one of these six newly complete tow... Details \| Contact Manager	Home	3 / 3.5 / 6	$558 - $658 Per Night $3906 - $4606 Per Week
More Photos Olivia Cottage Key West 30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's "Guestbook" column, th... Details \| Contact Manager	Home	2 / 2.5 / 4	Contact Owner Directly For Rates
More Photos Bloom'n Paradise Key West Relax in luxury in this beautiful Truman Annex private home. This property features three bedrooms a... Details \| Contact Manager	Home	4 / 4 / 8	$5500 - $7500 Per Week
More Photos Newton Street Hideaway Key West 30 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located j... Details \| Contact Manager	Home	1 / 2 / 2	Contact Owner Directly For Rates
More Photos Elizabeth Retreat Key West 30 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet resident... Details \| Contact Manager	Home	3 / 2 / 6	Contact Owner Directly For Rates
More Photos Colony Poolside Key West Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas ... Details \| Contact Manager	Condo	1 / 1 / 2	$190 - $250 Per Night $1260 - $1680 Per Week
More Photos Leeward Isle Key West Retreat Key West LEEWARD ISLE KEY WEST RETREAT -- Dwell in the possibility! From the moment you park in the private ... Details \| Contact Manager	Condo	2 / 2 / 4	$265 - $471 Per Night $1575 - $2900 Per Week
More Photos Dreaming On Duval Key West There's a new place on Duval Street in historic Key West and it is unique! Dreaming On Duval premie... Details \| Contact Manager	Home	5 / 4 / 10	$870 - $2000 Per Night $5950 - $14000 Per Week