Hyatt Windward Pointe Resort

Key West, Florida

Hyatt Windward Pointe Resort

Key West, Florida

Timeshare rentals

$286 - $600 /night

Starting at $286 /night

View all timeshare rentals

Timeshare resales

$498 - $16,498

Starting at $498

View all timeshare resales

Timeshare Owner?

Post your timeshare at Hyatt Windward Pointe Resort for rent or sale in less than five minutes!

Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale resort ambiance. Here is a retreat where you can slow down and forget the rush and stress of your day-to-day life. Bask beside the lushly landscaped pool that gives you the illusion that you’re softly floating on the open sea, grab a snack at Abbey Road poolside sandwich and snack bar or get your blood pumping at the fitness center at site resort Hyatt Key West Resort & Spa. Read more »

All of the ultra-spacious, ultra-plush residences at Hyatt Windward Pointe features two bedrooms - the master bedroom with a king bed and adjoining bath outfitted with a walk-in shower and spa tub, and the guest bedroom with a queen bed. Ocean, pool and courtyard views are available, and everyone is sure to take advantage of the convenience offered by a full kitchen, dining area, living room, TV, fully-furnished balcony and complimentary Wi-Fi access!

Hyatt Windward Pointe Resort's convenient location puts you just minutes from the free-spirited art, music and entertainment scene of Old Town. Or, head over to nearby Smathers Beach, the biggest white sand beach in Key West to rent windsurfers or go parasailing. The keys are also a haven for anglers - shallow flats, mangrove islands, inland channels and open blue waters offer world-classing fishing opportunities. Hoping to test your skills on the green? You're in luck - Key West Golf Club is located nearby and is the only Caribbean inspired course in the U.S.

Room Types

All rooms are identical at Hyatt Windward Pointe Resort:

2 Bedroom Condominium

2 Bathrooms, Full kitchen, Sleeps 6

Room Details →

28 Rentals from $286/night 33 Resales from $498


On-Site Features & Amenities

  • Accessible units
  • Bar
  • Clubhouse
  • Internet access
  • Movie rentals
  • Outdoor pool
  • Restaurant
  • Sauna
  • Shared laundry facilities
  • Whirlpool/hot tub

Nearby Attractions

  • Boating
  • Drug store
  • Fishing
  • Fitness center
  • Golf
  • Grocery store
  • Hiking
  • Live entertainment
  • Medical facilities
  • Playground area
  • River
  • Scuba diving
  • Shopping area
  • Spa services
  • Tennis
  • Water skiing
  • Wind surfing

Policies

  • No Pets
  • No Smoking
  • Minimum check-in age: 21
  • Check-in time: 4:00 PM
  • Check-out time: 10:00 AM

Recently stayed at Hyatt Windward Pointe Resort? Share any resort updates we should know about.

4.8 out of 5
  • 5

    (128)

  • 4

    (14)

  • 3

    (3)

  • 2

    (2)

  • 1

    (2)

  • Resort location
  • Staff/Service
  • Cleanliness
  • Sleep comfort
  • A beautiful property with spacious and fabulous two bedroom condominiums. The pool is large and grounds are well maintained and gorgeous....

    Read more »
    By ritap86 Updated Dec 23, 2022
    Helpful? 1 0
  • VERY NICE RESORT WITH NICE POOL AND SHACK BAR WITH A SHORT WALK FROM AIRPORT. A GREAT 2 BEDROOM CONDO WITH EVERYTHING YOU NEED FULL...

    Read more »
    By donaldg243 Updated Dec 23, 2022
    Helpful? 1 0

Questions & Answers

There is a wonderful walking or jogging path directly across from Windward... Read more »
Stephen H. answered Jan 30, 2024
Helpful?   1 0 Report
No rollaway beds are available.
Stephen H. answered Feb 15, 2024
Helpful?   1 0 Report

See more discussions in the Hyatt Windward Pointe Resort forum →


Map & Address

3675 S Roosevelt Blvd
Key West, Florida 33040
Accuracy not guaranteed. Contact the resort to confirm the address before making plans.

Timeshare Rentals

$286 - $600 /night

View all timeshare rentals

Timeshare Resales

$498 - $16,498

View all timeshare resales

Own a timeshare at Hyatt Windward Pointe Resort?

Timeshare Rentals

Timeshares for rent at Hyatt Windward Pointe Resort

Oct 26 – Nov 2, 2025 7 Nights
Verified & Protected
New!
$3,000 ($429/night)
Jun 14–21, 2025 7 Nights
Verified & Protected
New!
$2,995 ($428/night)
Mar 14–16, 2025 2 Nights
New!
$800 ($400/night)
Dec 27, 2025 – Jan 3, 2026 7 Nights
New!
$4,199 ($600/night)
May 24–31, 2025 7 Nights
Verified & Protected
New!
$3,200 ($457/night)

Timeshare Resales

Timeshares for sale at Hyatt Windward Pointe Resort

Week: 15 (high)
Use: Odd Years, Type: Deed
New!
Price: $2,998
Maint. fee: $2,067
Week: 24 (high)
Use: Annual, Type: Deed
New!
Price: $4,498
Maint. fee: $2,094
Week: 25 (high)
Use: Annual, Type: Deed
New!
Price: $1,800
Maint. fee: $1,812
Week: 20 (high)
Use: Even Years, Type: Deed
Price: $3,479
Maint. fee: $1,980
Points: 2,200
Banked: 0
Anniv: April
Use: Annual
Type: Deed
Price: $4,788
Maint. fee: $2,097

Points/Credits for sale

System Postings Available Price
P Hyatt Vacation Club 25 400 - 510,000 $0 - $35,000 View all