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Nightly Vacation Rentals for Groups
Perfect for a family, wedding party or a friendly gathering in Key West.

Sleeps 10 People - Old Town Key West, just steps away from Duval Street
Please click on a name for photos, description and how to inquire.
RATE SCHEDULE
Winter
Dec. 15 thru
April 30
Shoulder
May & November
Summer
June 1 - Oct 31
Dec. 1 - Dec. 14

Tres Flores
(Rate Based on 10)
3 Q BR/ / 2 Sl. Sofas / 3 Baths
Parking for 3 vehicles
Access to 2 Pools

Free WiFi

$588
$438
$378

Tres Flores group vacation rental lodgingTres Flores Located on the 500 block of Simonton Street, just 1 block off Duval Street, this complex is at the center of the old town excitement. Tres Flores is a combination of 3 condos that share the same building. Hibiscus Suite is a queen efficiency with a kitchen, bathroom and a small outdoor deck. Orchid and Jasmine are both one bedroom suites with queen bedrooms, queen sleeper sofas, kitchenettes and outdoor decks. All units have TV/DVD, cable and Free WiFi! This complex offers combined parking for 3 vehicles, a BBQ grill and access to 2 pools located a few blocks down the road at our Center Court Courtyard. If you want to be downtown near the action with the added bonus of off street parking, then this is the perfect place for your group!


Sleeps up to 12 People (with Private Jacuzzi) - Old Town Key West

Abbey Road
(Rate Based on 10)
5K BR, 1 Q.Sl.Sofa)/4 Baths
4 Private Jacuzzis
Free WiFi



$1028
$828
$728

The Breezes of Key West vacation rentalsAbbey Road- Completely renovated January, 2010, the private, gated compound is comprised of 4 luxury units,  Lennon’s Lodge (Sleeps 6 with 8 person Jacuzzi), McCartney’s Manor (Sleeps 2 with 2 person Jacuzzi), Starr’s Suite (Sleeps 2 with 2 person Jacuzzi) and Harrison’s Hideaway (Sleeps 2 with 2 person Jacuzzi) and will accommodate up to 12 persons for the ultimate in privacy!

The common area has a bike rack, Weber gas BBQ grill and a washer/dryer for your use.  Upstairs, on the deck overlooking lushly landscaped Abbey Road, is a common area with outdoor table and chairs and ice-maker.  Take your computer there to do some work, if you must, with our free wi-fi.

Located next door is one of our 2 heated pools for working on that perfect tan!  Call us today to reserve this special private Key West compound just ½ block off Duval Street!


Tradewinds
(Rate Based on 8)
4 K BR/2 Q Sl. Sofas/2 Baths
2 Private Jacuzzis
2 Off-Street Parking Spaces

$588
$498
$428

The Breezes of Key West vacation rentalsTwo Cigar Maker’s Cottages, side-by-side, located ½ block off Duval Street. These two cottages are a favorite of our guests who like to relax in the private, quiet, beautiful garden areas with large spas that are behind each house. Your party can book these cottages for a relaxing vacation, just steps from Duval Street.


Sleeps up to 12 People (with Private Jacuzzi) - Old Town Key West

Palm Gardens
(Rate Based on 12)
3 K BR/3 Q Sl. Sofas/3 Baths
3 Private Jacuzzis
Free WiFi



$708
$578
$498

The Breezes of Key West vacation rentalsPalm Gardens – A small Condo complex located at 905 & 907 White Street, consisting of three (3) 1 Bedroom/1 bath Condos. The Condos are tied together in a lushly landscaped garden setting with a spa pool in the rear. Booking all 3 condos gives you a great alternative to booking a single house as you are offered privacy and closeness at the same time. Call to book your Island Paradise while there is still time!

Sleeps up to 16 People (with Private Heated Pool) - Old Town Key West

Almost Southernmost Retreat
(Rate based on 12)
2K’s, 4Q’s, 2 Qsl
5 Bedrooms, 3.5 Baths
+ 2 Outdoor Showers
Large Jacuzzi
& Private heated pool
Free Wi-Fi



$958
$758
$598

Almost Southernmost RetreatAlmost Southernmost Retreat- at 415 and 417 Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Retreat is a perfect example of shotgun architecture with front porches and back decks on the side by side historic cottages. The style is common throughout the islands.  Located in a row of identical cigar-maker cottages, the front porches are perfect for people watching in old town.  There is also a second story deck at 417 for sunbathing.  A gate at the rear of the two houses allows folks to enjoy each other’s company in total privacy!


Casa Grande
(Rate based on 10)
2K BRs, 3Q BRs, Qsl, 1 Trundle, 5½ Baths
Private heated pool
Private parking for 2 vehicles

Free Wi-Fi



$1058
$858
$698

The Breezes of Key West vacation rentalsCasa Grande – Casa Grande is a recently renovated luxury home in the heart of old town Key West. Located on Amelia Street, quiet lane just steps from World Famous Duval Street, you will have an easy walk to the Night Life and a quiet place to return to.

Sleeps up to 26 People - Old Town Key West

Old Town Garden Villas
5K, 2Q (6Q sl)
7Baths, 3(1/2)Baths
Shared Heated Pool on Premises
Free Wi-Fi

Ask about group rates!

Flagler Suite part of Simonton Court vacation rentalsOld Town Garden Villas are a part of 12 Villas located in a gated courtyard surrounded by flowers, a fountain & a gazebo to create a serene Garden area. The location is set on Center Street, which is located ½ block off Duval Street. These Villas are a favorite of our guests who like to relax in the quiet, beautiful garden area. Your party can book out 1 to 6 of these Villas for a relaxing vacation.

 

 

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Key West Vacation Rentals
1075 Duval Street, C-19 ~ Key West, FL 33040
305-296-9292 ~ (800) 797-8787 ~ (800) 294-9560 | Email us: reservations@vacationrentalskeywest.com

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