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Our top choices for Fleming Key hotels

Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very good, (1006)
"It was so nice experience to stay there."
United States
Tapas
The price is NZ$386
includes taxes & fees
19 Jan - 20 Jan 2026
Sugar Loaf Lodge

The Conch House Heritage Inn

The Conch House Heritage Inn
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (147)
Soak in Old Town Key West's charm at this B&B with an outdoor pool and free breakfast. Just a 10-minute walk to Duval Street and Hemingway's Home. Florida Keys Beaches and Southernmost Point are within 15 minutes, while water adventures await nearby.

"Check in was quick, easy. "
United States
kristen
The price is NZ$788
includes taxes & fees
11 Jan - 12 Jan 2026
The Conch House Heritage Inn

Artist House Key West

Artist House Key West
3.5 star property
Key West Historic District
9.8 out of 10, Exceptional, (422)
Experience the artistic heart of Key West at this charming B&B. Just a 10-minute walk to Duval Street and Florida Keys Beaches, with Mallory Square and Hemingway's Home nearby. Enjoy the spa pool, free breakfast, and WiFi while exploring local trails.

"Really great place to stay. Nice rooms and staff. Great location for Devaul street. "
United States
Beth
The price is NZ$569
includes taxes & fees
15 Jan - 16 Jan 2026
Artist House Key West

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
4.0 star property
Old Town Key West
8.4 out of 10, Very good, (492)
Unwind at this historic Key West resort featuring 2 outdoor pools and a private beach with spectacular sunset views. Just minutes from Duval Street and South Beach, enjoy beach massages, volleyball, and cold drinks at the beach bar after exploring local attractions.

"Great place"
United States
ELENA
The price is NZ$982
includes taxes & fees
13 Jan - 14 Jan 2026
Casa Marina Key West, Curio Collection by Hilton

H2O Suites - Adults Only

H2O Suites - Adults Only
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (582)
Escape to this adults-only Key West haven with a stunning rooftop terrace and refreshing outdoor pool. Enjoy poolside drinks, workout in the fitness centre, and explore nearby South Beach, all with free WiFi and exceptional staff service.

"Great place!!"
United States
Joel
The price is NZ$1,086
includes taxes & fees
4 Jan - 5 Jan 2026
H2O Suites - Adults Only

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (136)
Steps from Duval Street, this LGBTQ-friendly retreat features a refreshing outdoor pool and soothing spa pool. Wake up to free breakfast before exploring Key West attractions. Relax in the garden or terrace after your adventures. The exceptional staff ensures a memorable stay.

"We absolutely loved finding this gem to stay on our first visit to Key West. Great location, wonderful staff, and excellent room. "
United States
Sammy
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
3.5 star property
Key West
9.6 out of 10, Exceptional, (1007)
Experience island tranquility at this Key West hotel, just minutes from Smathers Beach and Duval Street. The resort offers a refreshing outdoor pool, spa pool, and convenient dining at the restaurant and snack bar. Free WiFi and parking add value to your Florida Keys escape.

"Clean rooms, great location."
United States
Shalaka
The price is NZ$916
includes taxes & fees
7 Jan - 8 Jan 2026
Hyatt Vacation Club at Windward Pointe, Key West

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
4.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (1003)
Located just minutes from Duval Street and Mallory Square, this coastal retreat offers breathtaking ocean views. Relax at the outdoor pool, enjoy treatments at the spa, or dine at 2 restaurants with 3 bars to choose from. Guest reviews praise the helpful staff and prime location.

"Location, large rooms"
United States
george
The price is NZ$997
includes taxes & fees
13 Jan - 14 Jan 2026
Ocean Key Resort - A Noble House Resort

Santa Maria Suites

Santa Maria Suites
4.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (1001)
Just 5 minutes from Duval Street and Florida Keys Beaches, this resort offers 2 outdoor pools and poolside bar. Milagro restaurant serves dinner after a workout in the fitness centre. In-room washing machines/dryers and sofa beds add convenience near Southernmost Point.

"Awesome place we loved it"
United States
Josh
The price is NZ$1,066
includes taxes & fees
13 Jan - 14 Jan 2026
Santa Maria Suites

Tropical Inn

Tropical Inn
3.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (364)
Charming B&B featuring a refreshing outdoor pool and soothing spa pool in Key West's historic district. Gardens and a terrace create a peaceful retreat, while free breakfast and WiFi enhance the experience, all near popular attractions.

"Nice place to stay "
United States
yulio
The price is NZ$580
includes taxes & fees
4 Jan - 5 Jan 2026
Tropical Inn

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Key West Historic District
9.8 out of 10, Exceptional, (1001)
"Perfect place to stay. "
United States
Paulette
The price is NZ$872
includes taxes & fees
4 Jan - 5 Jan 2026
The Marquesa Hotel

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
4.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (1002)
Discover tranquility at this Key West resort offering spectacular ocean views and a private beach area with clear warm waters. Guests praise the quiet setting, full-service spa, and marina. Explore Mallory Square or enjoy sunset cocktails after a refreshing swim.

"Staff was courteous and the location is perfect for a weekend in Key West."
United States
TIMOTHY
The price is NZ$985
includes taxes & fees
7 Jan - 8 Jan 2026
Hyatt Centric Key West Resort and Spa

The Mermaid & Alligator

The Mermaid & Alligator
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (276)
Just 10 minutes from Duval Street and Hemingway's Home, this charming guesthouse offers a refreshing outdoor pool and complimentary full breakfast. Guests love the helpful staff and convenient location, with Florida Keys beaches within walking distance.

"Great place"
United States
Carol A
The Mermaid & Alligator

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1)
This holiday home offers a serene garden setting with free parking, just minutes from Key West's famous attractions. Enjoy easy access to Smathers Beach and Florida Keys coastline while being near vibrant Duval Street nightlife.

"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is NZ$3,897
includes taxes & fees
20 Jan - 21 Jan 2026
Capmar House by Brightwild Huge Home Pool

Coco Plum Inn

Coco Plum Inn
3.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (470)
Enjoy the outdoor pool at this welcoming guesthouse near Duval Street and Ernest Hemingway Home. Guest rooms include convenient refrigerators and microwaves. Take advantage of free breakfast and WiFi before exploring nearby kayaking and snorkelling options.

"The Coco Plum Inn is a wonderful place to stay. Staff is fantastic and the location is perfect. We will definitely come back and stay at the Coco Plum Inn."
United States
Brent
The price is NZ$610
includes taxes & fees
4 Jan - 5 Jan 2026
Coco Plum Inn

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West
3.5 star property
Key West
9.4 out of 10, Exceptional, (1011)
Unwind at this coastal haven minutes from Duval Street, featuring a relaxing spa pool and bar/lounge. Free WiFi and parking enhance your stay near Smathers Beach and Hemingway's home. Clean rooms and helpful staff ensure a memorable Florida Keys escape.

"Location, swimming pool, hot tub and the awesome patio that the room had"
United States
Anshul
The price is NZ$902
includes taxes & fees
21 Jan - 22 Jan 2026
Hyatt Vacation Club at Beach House, Key West

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns
3.5 star property
Key West Historic District
9.2 out of 10, Wonderful, (862)
Discover charming accommodation in Key West with easy access to Duval Street and Florida Keys Beaches. After a refreshing swim in the outdoor pool, explore nearby attractions like Mallory Square and Ernest Hemingway Home, all within 15 minutes.

"What a amazing place to stay from the service to the rooms spectacular "
United States
John
The price is NZ$854
includes taxes & fees
13 Jan - 14 Jan 2026
Ridley House - Key West Historic Inns

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
Old Town Key West
8.6 out of 10, Excellent, (326)
"Great location and staff was friendly. The pool area was perfect. "
United States
Deborah
The price is NZ$622
includes taxes & fees
8 Jan - 9 Jan 2026
Hyatt Vacation Club at Sunset Harbor, Key West

Southernmost House

Southernmost House
4.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (1002)
Immerse yourself in Key West luxury at this Victorian gem. Enjoy the outdoor pool and poolside bar overlooking the ocean, with South Beach nearby. The Seaside Café serves lunch and dinner, while complimentary breakfast starts each day perfectly.

"Great place to stay. Staff was very friendly"
United States
Jacob
The price is NZ$874
includes taxes & fees
14 Jan - 15 Jan 2026
Southernmost House

Seascape Tropical Inn - Adult Exclusive

Seascape Tropical Inn - Adult Exclusive
3.0 star property
Old Town Key West
9.0 out of 10, Wonderful, (406)
This adult-exclusive Key West inn combines Victorian elegance with tropical serenity. Enjoy the complimentary breakfast before exploring nearby attractions. The peaceful garden and inviting terrace provide perfect spots to unwind after sightseeing adventures.

"We had a great stay. Room was clean, staff was helpful, check un easy. "
United States
Suzanne
The price is NZ$517
includes taxes & fees
4 Jan - 5 Jan 2026
Seascape Tropical Inn - Adult Exclusive
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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