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Tropical Village

12 Bedrooms
9 Bathrooms
5.0000
(24 Reviews)
Tropical Village is comprised of 6 separate vacation rentals properties that can also be rented separately.
Located at 706 and 708 South St - near The Southernmost Point - this nightly group unit is the perfect getaway spot for large groups of friends and family.

COTTAGE @ TROPICAL VILLAGE:...

Tropical Breeze

Studio
1 Bathroom
4.2424
(66 Reviews)
Tropical Breeze is decorated in a tropical motif, with a cozy palm frond matelassé. There are wood and wicker furnishings throughout. Traditional Key West shutters allow the floral scents and chirping of birds to drift through the room.

The door opens onto our second story landing where you are...

Papa's Hideaway #1 - Torrents of Spring

Studio
1 Bathroom
4.7059
(102 Reviews)
Papa's Hideaway was a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval street. The perfect mix of location, atmosphere and value.

Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling...

Sunrise Suites - Dominican Suite 110

2 Bedrooms
2 Bathrooms
4.4583
(48 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Old Town Garden Villas

5 Bedrooms
6 Bathrooms
4.9231
(26 Reviews)
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 1 to 5 of these Villas for a relaxing vacation.

Old Town Garden Villas is comprised of the following...

Banana Breeze @ Key Cove

4 Bedrooms
3 Bathrooms
Newly Decorated And Fully Appointed With Water View *30 NIGHT MIN STAY REQUIRED*

Look out at the open water views while enjoying the professionally decorated interior and spacious outdoor patio. Imagine relaxing at "Banana Breeze" with friends, family or both while listening to island music and...

Sunrise Suites - Tierra Bomba Suite 403

2 Bedrooms
2 Bathrooms
4.3043
(46 Reviews)

Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Shark Key Chateau

5 Bedrooms
4 Bathrooms
4.7500
(8 Reviews)
Château - Merriam-Webster defines it as a "large impressive residence". This does not do the 'Shark Key Chateau' justice! Very impressive, very large, very luxurious! Set apart from any residence you have experienced. But this property does not rest on

Shark Key Chateau is 'Grande' to say the...

Southernmost Retreat

2 Bedrooms
1 Bathroom
4.6591
(88 Reviews)
Southernmost Retreat features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. The perfect place to listen to your favorite music while...

Truman @ Duval - Two Bedroom

2 Bedrooms
1 Bathroom
4.4490
(98 Reviews)
Truman at Duval - if you're looking for South Beach slick-- not here!

If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people...

Curry House Room 3

Studio
1 Bathroom
4.6750
(80 Reviews)
An excellent value, Room 3 is delightful and comfortable. This room is unique in the Curry House in that it is the only room with French doors that open up onto the second-floor porch. Room 3 shares a bathroom with Room 4. The bathroom is exclusive to these two rooms and has an island charm all it'...

Mary's Backyard

1 Bedroom
1 Bathroom
4.9118
(68 Reviews)
This 1 bedroom, 1 bathroom unit is right downtown and features everything you will need for your Key West getaway! Located next door to other vacation rentals such as Mary's Backyard Too and Banana's Foster Guesthouse and across the street from Seaport Suite.

The location itself could not be...

Papa's Hideaway #2 - The Sun Also Rises

Studio
1 Bathroom
4.6087
(92 Reviews)
Papa's Hideaway was an historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval Street. The perfect mix of location, atmosphere and value.

This studio is located on the second floor and offers a king-size bed, queen-size sleeper sofa,...

Osprey Suite

Studio
1 Bathroom
4.5135
(74 Reviews)
Part of Southernmost Sanctuary Suites

The Osprey Suite - Located in the Garden at the Southernmost Studios, the Osprey Suite is the perfect island getaway. Located within walking distance to all of the charms in Old Town you'll never want to leave! The Osprey has a Queen Bed as well as a sofa for...

Tropical Village - Tropical Cottage

2 Bedrooms
2 Bathrooms
4.6364
(66 Reviews)
Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is your ticket to a stress free...

Villa Azul

3 Bedrooms
3 Bathrooms
5.0000
(2 Reviews)
You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old Town, just 4 blocks to the Historic Seaport District or the Art Gallery District on White...

Shipyard Hideaway

2 Bedrooms
1 Bathroom
4.6667
(6 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.***

****Exterior of property being painted 9/25-10/6****

This 2 bed 1 bath unit is located in the quiet and desirable Truman Annex neighborhood. You will be just a short walk from both the liveliness of Duval St...

Nautical Wheeler @ Key Cove

4 Bedrooms
3 Bathrooms
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Nautical Wheeler. This home is located in the private community of Key Cove Landings, on an...

Casa Hueso

4 Bedrooms
3 Bathrooms
**There will be construction in the surrounding developing area on and off for the next year**

Trade in your stressful workdays and chilly weather for a fresh ocean breeze and plenty of sunshine! This Newly Built Key West Home has more than enough space for all your friends and family to share...

Papa's Hideaway - Garden of Eden

2 Bedrooms
2 Bathrooms
4.8462
(156 Reviews)
Located at Papa's Hideaway, the serene grounds strike you immediately upon entering the beautifully landscaped, gated property. Located just one block off World Famous Duval Street, Garden of Eden is the perfect combination of quiet Key West living and optimum access to all of the islands best...

Garden of Roses

3 Bedrooms
2 Bathrooms

Originally built in 1933, this fully renovated, three-bedroom home has a yard, a cozy front porch where you can sit back and watch the day go by, and room for up to eight guests (six comfortably). Stroll to shopping, entertainment, and beaches, all within a few blocks of this rental....

Writer's King Room

Studio
1 Bathroom
4.6190
(42 Reviews)
The Writer's King is located at the end of our second floor balcony at our Key West lodging, located directly over the Lagoon where you can listen to our gentle waterfall on cool evenings.

Featuring a King size bed with Tiffany reading lamps, the Writers' King is a relaxing way to enjoy your Key...

Bougainvillea

Studio
1 Bathroom
4.2647
(68 Reviews)
The Bougainvillea is located just steps from our heated pool and adjacent to the Hibiscus Room. Both share a large semi-private deck, which has access to the front yard and the pool area.

This arrangement is perfect for couples traveling together: plenty of common space and plenty of privacy. The...

Palm Gardens

3 Bedrooms
3 Bathrooms
4.9474
(38 Reviews)
The Condos are tied together in a lushly landscaped garden setting with a spa pool in the rear. Booking all three 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!...

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