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For Rent
2 bed
North America | USA | FL | Key West
$2300.00
Week 9
Fixed - Check In 03/02/25 Check Out 03/09/25
2025
Perfect Time of Year in Key West!
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LISTING
272634
WEEK
9
CHECK IN
03/02/25
CHECK OUT
03/09/25
TYPE
Fixed
BEDROOMS
2
BATHROOMS
2
SLEEPS
6
PRICE
$2300.00
Perfect Time of Year in Key West!

Beautiful resort with lush grounds and pool on the Gulf side of Key West with views of the gulf and pool. This is high season in Key West and most hotel rooms are at least $450 a night. Comfortable screened in porch allows for complete relaxation and view of the pool and Atlantic. Tiki hut/Cafe on the grounds. Sleeps six with a hide-abed. Free covered parking and short drive to Old Town Key West. Unit also has full kitchen, dining area and a washer and dryer.
Last updated 02/01/2025
TUG member since 2014
For Rent
2 bed
North America | USA | FL | Key West
$3600.00
Week 14
Fixed - Check In 04/06/25 Check Out 04/13/25
2025
The Best Hotel in Town
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LISTING
274008
WEEK
14
CHECK IN
04/06/25
CHECK OUT
04/13/25
TYPE
Fixed
BEDROOMS
2
BATHROOMS
3
SLEEPS
6
PRICE
$3600.00
The Best Hotel in Town

Location Location Location. Verry difficult to reserve. Sunday check in only. This is a beautiful, two floor, two bed room, two balconies. Unit 532. Sleeps 6, and it is an Oceanview so you can sit on your balcony and enjoy the sunset.
The upstairs master has a balcony with a great view of the ocean and a private en-suite with tub and shower. The second bedroom also has its own bathroom and shower. The downstairs has a full kitchen, dining area and big living room area. The pool area is nice and quiet and we've never had a problem getting chairs. Duvall Street is just a short walk away. This is a wonderfully relaxing vacation spot.
Last updated 01/20/2025
TUG member since 2023
For Rent
2 bed
North America | USA | FL | Key West
$2400.00
Week 18
Fixed - Check In 05/04/25 Check Out 05/11/25
2025
5* star resort in the Keys
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LISTING
274476
WEEK
18
CHECK IN
05/04/25
CHECK OUT
05/11/25
TYPE
Fixed
BEDROOMS
2
BATHROOMS
2
SLEEPS
6
PRICE
$2400.00
5* star resort in the Keys

Float in the infinity edge pool on the ocean,enjoy the view from your furnished patio.Take advantage of the Key West resort and spa!Full kitchen,outdoors grill for your cooking or enjoy the numerous restaurants!
Last updated 02/05/2025
TUG member since 2011
For Rent
2 bed
North America | USA | FL | Key West
$4000.00
Week 21
Fixed - Check In 05/24/25 Check Out 05/31/25
2025
MEMORIAL DAY IN KEY WEST, BEST OLD TOWN LOCATION, WALK TO MINIMAL REGATTA AT SCHOONERS
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LISTING
273609
WEEK
21
CHECK IN
05/24/25
CHECK OUT
05/31/25
TYPE
Fixed
FREQUENCY
EY
BEDROOMS
2
BATHROOMS
2
SLEEPS
6
PRICE
$4000.00
MEMORIAL DAY IN KEY WEST, BEST OLD TOWN LOCATION, WALK TO MINIMAL REGATTA AT SCHOONERS

MEMORIAL DAY IN KEY WEST, 2-2 FOR UP TO SIX, ONE PARKING SPOT INCLUDED, OTHER SPOTS CLOSE FOR FEE.

WK 22 and 23 AVail in D bldg same price

DON'T NEED CAR, WALK OR UBER TO BEST OF KEY WEST.
GREAT WK FOR FISHING, MAHI MAHI, WAHOO SAILFISH ETC
NICE MARINA VIEW FROM D-34, VERY CLOSE TO JETTY TO WATCH WILDLIFE CRUISE THRU OR FISH
PRIVATE (RARE) BEACH AND FISHING PIER
BRAND NEW HUGE GAS GRILLES FOR YOUR OUTDOOR ENJOYMENT,
3% CONVENIENCE FEE FOR CC
Last updated 02/08/2025
TUG member since 2006
For Rent
1 bed
North America | USA | FL | Key West
$2200.00
Week 23
Fixed - Check In 06/08/25 Check Out 06/15/25
2025
June Rental
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LISTING
273867
WEEK
23
CHECK IN
06/08/25
CHECK OUT
06/15/25
TYPE
Fixed
BEDROOMS
1
BATHROOMS
1
SLEEPS
4
PRICE
$2200.00
June Rental

Hyatt Sunset Harbor – A Perfect Slice of Paradise

My recent stay at Hyatt Sunset Harbor in Key West was nothing short of incredible. This property is a true gem, offering a perfect combination of location, comfort, and Key West charm.

Location
Situated right in the heart of Old Town Key West, Hyatt Sunset Harbor provides easy access to all the must-visit spots. It's a stone’s throw from Mallory Square, making it ideal for catching those famous sunsets, and just a short walk to Duval Street's lively bars, restaurants, and shops. Despite being in the center of the action, the resort maintains a tranquil, private ambiance.

Accommodations
The rental unit was spacious, well-appointed, and impeccably clean. The furnishings were modern yet cozy, with a distinct Key West flair. The kitchen was fully equipped, perfect for preparing meals, though with so many great dining options nearby, we didn’t use it much! The private balcony overlooking the harbor was the highlight—it offered breathtaking views of the water and was the ideal spot for morning coffee or evening cocktails.

Amenities
The resort features a lovely pool area with plenty of lounge chairs and umbrellas, providing a serene escape from the hustle of downtown. There’s also a hot tub, which is great for unwinding after a day of exploring. The staff was incredibly friendly and attentive, always ensuring we had everything we needed.

Overall Experience
If you're looking for a combination of luxury, convenience, and relaxation, Hyatt Sunset Harbor is an excellent choice. It’s perfect for couples, families, or solo travelers who want to enjoy everything Key West has to offer without compromising on comfort.

I can’t wait to return to this little slice of paradise!
Last updated 02/05/2025
TUG member since 2025
For Rent
2 bed
North America | USA | FL | Key West
$4000.00
Week 30
Fixed - Check In 07/26/25 Check Out 08/02/25
2025
Galleon Resort - Mini Lobster - Week 30 - A Building
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LISTING
271832
WEEK
30
CHECK IN
07/26/25
CHECK OUT
08/02/25
TYPE
Fixed
FREQUENCY
EY
BEDROOMS
2
BATHROOMS
2
SLEEPS
6
PRICE
$4000.00
Galleon Resort - Mini Lobster - Week 30 - A Building

See Galleon web page for more info: https://www.galleonresort.com/
Last updated 01/22/2025
TUG member since 2016
For Rent
2 bed
North America | USA | FL | Key West
$3300.00
Week 31
Fixed - Check In 08/02/25 Check Out 08/09/25
2025
The Galleon Resort - Start of Lobster Season! - Week #31 Rental
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LISTING
271834
WEEK
31
CHECK IN
08/02/25
CHECK OUT
08/09/25
TYPE
Fixed
FREQUENCY
EY
BEDROOMS
2
BATHROOMS
2
SLEEPS
6
PRICE
$3300.00
The Galleon Resort - Start of Lobster Season! - Week #31 Rental

Gulf View, Galleon Resort, Downtown Key West:: A little bit of Heaven on Earth! Suite and Balcony overlook Gulf, Beach, Pool and Tiki bar. Magnificent Sunrise and sunset 360 Degree views from the top floor overlook. 2Br, 2Ba unit, recently refurbished and fully equipped kitchen. In Suite washer and dryer, kitchen table, dining room table for 4 or breakfast at the kitchen counter bar. and more!!!
Last updated 01/22/2025
TUG member since 2016
For Rent
2 bed
North America | USA | FL | Key West
$3200.00
Week 43
Fixed - Check In 10/25/25 Check Out 11/01/25
2025
Galleon Resort (Old Town) Fantasy Fest Parade 2025
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LISTING
272398
WEEK
43
CHECK IN
10/25/25
CHECK OUT
11/01/25
TYPE
Fixed
BEDROOMS
2
BATHROOMS
2
SLEEPS
6
PRICE
$3200.00
Galleon Resort (Old Town) Fantasy Fest Parade 2025

Catch the last day of Fantasy Fest 2025 (including Fantasy Fest parade 10/25)

Located at the beginning of the Harbor Walk and two blocks from Duval street. No need to rent a car, you can walk to many restaurants and bars. This unit has a pool and partial water view. A small resort fee is charged by the resort and collected at check-in.

Housekeeping changes linens and towels on Wednesday. Daily housekeeping is available for an additional charge imposed for by the resort.

BBQ grills are available on the property, also a dock that provides a spectacular view of the sunset and a rooftop observation deck overlooking the Gulf and Key West Marina.

There is a Tiki bar with live music daily on the dock and a snack bar on site for coffee and sandwiches.

Parking pass for one car included.
Last updated 12/28/2024
TUG member since 2006
For Rent
2 bed
North America | USA | FL | Key West
$3500.00
Week 50
Fixed - Check In 12/14/25 Check Out 12/21/25
2025
Waterfront Unit in Key West!
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LISTING
274415
WEEK
50
CHECK IN
12/14/25
CHECK OUT
12/21/25
TYPE
Fixed
BEDROOMS
2
BATHROOMS
2
SLEEPS
6
PRICE
$3500.00
Waterfront Unit in Key West!

Week before Christmas in a 2 bedroom waterfront unit at Hyatt Sunset Harbor.

Unit 532
Last updated 02/04/2025
TUG member since 2006
For Rent
2 bed
North America | USA | FL | Marathon
$1050.00
Week 3
Fixed - Check In 01/18/26 Check Out 01/25/26
2026
oceanside mile marker 50
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LISTING
272086
WEEK
3
CHECK IN
01/18/26
CHECK OUT
01/25/26
TYPE
Fixed
BEDROOMS
2
BATHROOMS
2
PRICE
$1050.00
oceanside mile marker 50

2 bdr 2 bath sleeps 6
Last updated 01/27/2025
TUG member since 2009





 
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