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Key West Vacation Rentals in the Florida Keys

Book Your Key West, Florida Keys Vacation Rentals Directly Online Here and Save!

Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Key West, Florida Keys, Florida.

We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of home rentals to choose from, we now have the selection and value to offer our visitors going to Florida.

Blue Pelican - Key West House

Blue Pelican - Comes With 6 Passenger Gas Golf Cart

Beautiful, BRAND NEW open floor plan, custom décor, private pool, gas golf cart, and ALL the amenities! KITCHEN Modern chef’s kitchen, with large island seating overlooking the beautifully appointed dining, living area, and sparkling pool. Fully stocked to the nines with chef’s quality appliances and cooking tools, as well as coordinating.......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Island Escape in Truman Annex - Key West Condo

Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex

This lovely Island Escape Condo is a upper level condo located in the Truman Annex Shipyard a luxury gated community. Not just another rental property! Location is everything.!!! Our favorite room is the spacious covered deck that opens up from living room with ceiling fans, tropical foliage, dining/sitting for 4. The Living/Dining area has couch,.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Condo Rentals

Vacation Home

Bahama Brilliant - Key West House

**BAHAMA BRILLIANT @ THE BEACH** Colorful Private Home & Pool + LAST KEY SERVICE

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! A true island treasure, BAHAMA BRILLIANT captures the essence and beauty of living in the Caribbean. Located just two blocks from Higgs Beach, this modern home was built to a high standard and decorated in vibrant colors to enhance the tropica.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 7 House Rentals

Vacation Home

Colors of the Keys - Key West Townhome

**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! COLORS OF THE KEYS is a bright and vibrant townhome that embodies Key West’s colorful & tropical spirit. Located within Truman Annex, Key West's most exclusive gated community, this home is within walking distance of all that Key West ha.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 6 Townhome Rentals

Vacation Home

Smooth Sailing - Key West Condo

**SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Formerly La Bonne Vie, SMOOTH SAILING has been meticulously furnished with a modern coastal feel, and the only beauty that competes with the interior is the spectacular views from your private oceanfront balcony. You'll be able to enjoy quiet .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

"JUST OFF DUVAL" ~ Heart of Key West! - Key West Condo

"JUST OFF DUVAL" ~ Charming Condo in Center of Duval St. with Parking Space!

STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items at this crisp condo centered in the heartbeat of Duval St. Located in the upbeat and lively district of Key West, this home is just steps to high end art galleries, museums, The Southernmost Point of the U.S. and all best nightl.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

DREAM MAKER at 1800 ATLANTIC - Key West Condo

NEWLY RENOVATED ...LAST MINUTE SPECIALS...CHECK DATES

PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Let us help make your dreams come true: Enjoy your tranquil view of the deep blue Ocean and sparkling salt water pool within our tropical garden.....There is nothing like it...anywhere. You don't have to spend a fortune to enjoy a spacious, clean and comfortable Key West condo. En.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

Suite Blu - Key West Apartment

Suite Blu - A monthly rental apartment in a great location

Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West. This monthly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided. This property will meet all of the demands a vacationer might have. Other amenities include a vaul.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Apartment Rentals

Vacation Home

Gulfside Vistas - Key West Condo

**GULFSIDE VISTAS @ THE ANNEX** Ocean Penthouse & Pool + LAST KEY SERVICE...

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! GULFSIDE VISTAS is a beautiful penthouse condo and is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You'll have ocean views on three sides of GULFSIDE VISTAS, and two s.......read more

2 Bedroom(s)
3 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

La Vie En Rose - Key West House

**LA VIE EN ROSE @ BEACHSIDE** Modern Home / Large Pool + LAST KEY SERVICES...

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! LA VIE EN ROSE is a classic mid-century modern home set in the Beachside district of Key West, just a couple blocks from Smathers Beach on Rose Street. As the lyrics to that sweet love song go, you'll be in 'a world apart'. You'll also be clos.......read more

4 Bedroom(s)
4 Bath(s) - Sleeps 10 House Rentals

Vacation Home

SIYC-1 - Key West Condo

Oceanfront Oasis Summ

Summary: A beautiful oceanfront suite located at the best marina in the Keys. Located off the azure waters of the Atlantic Ocean, minutes away from downtown Key West, known for its quaint boutiques, historic landmarks, sight-seeing, sunsets and dancing. Our condominium will provide you with an intimate lodging experience unlike any hotel. Our prope.......read more

1 Bedroom(s)
3 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

Vacation Rentals - Key West Boat

DESIGN YOUR OWN WATER ADVENTURE

A well appointed and renovated 36' Morgan Out Island Sloop, at ANCHOR with no dock, north of KW harbor . 2 guest MAXIMUM. Water and coffee complimentary. Water taxi transport is available for checking in and out between 5-7pm and 10-12 DISCOUNTED FOR MY GUESTS for insertion and extraction.For transport outside of those windows is a COST item fo.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 2 Boat Rentals

Vacation Home

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