
Islamorada, FL
10/16 – 10/18
$487/nighttotal: $974 (2 )
Guest Room, 2 Queens, Balcony, Free Parking & 3 Outdoor Pools
1 2hotel, Islamorada, Village of Islands
Directly on 15 oceanfront acres in Islamorada, this hotel offers direct beach and marina access, putting you within easy reach of Windley Key Fossil Reef Geological State Park and Indian Key Historic State Park, with Islamorada Brewery & Distillery and Florida Keys Brewing Co. just a short distance away.
This pet-friendly hotel features island-inspired rooms with 2 queen beds, a balcony, and complimentary toiletries, along with three outdoor pools, a fitness center, and on-site dining for a comfortable and convenient stay.
This pet-friendly hotel features island-inspired rooms with 2 queen beds, a balcony, and complimentary toiletries, along with three outdoor pools, a fitness center, and on-site dining for a comfortable and convenient stay.

Islamorada, FL
07/13 – 07/14
$545/nightfor 1 night
Island Oasis Stay | 3 Mi To Diving Museum | Snorkel & Learn Dive
1 4hotel, Islamorada, Village of Islands
Enjoy a pet-friendly hotel stay in Islamorada, Village of Islands, located oceanside on the scenic Overseas Highway in the Matecumbe neighborhood, offering easy access to fishing spots, beaches, Theater of the Sea, and Morada Bay.
This 370 sq. ft. hotel features 1 bedroom, 1 bathroom, and accommodates up to 4 guests with air conditioning, internet, a terrace/balcony, concierge services, and a shared outdoor pool, perfect for a dog-friendly Florida Keys getaway.
This 370 sq. ft. hotel features 1 bedroom, 1 bathroom, and accommodates up to 4 guests with air conditioning, internet, a terrace/balcony, concierge services, and a shared outdoor pool, perfect for a dog-friendly Florida Keys getaway.

Islamorada, FL
10/16 – 10/17
$978/nightfor 1 night
Enjoy Sunset Views From Your Villa With Pool & Beach Access In Fl
2 5hotel, Islamorada, Village of Islands
Enjoy sunset views from your 2-bedroom villa in Islamorada, Village of Islands, located in the Matecumbe neighborhood and just a short distance from Indian Key Historic State Park and Windley Key Fossil Reef Geological State Park.
This pet-friendly hotel offers 1042 sq. ft. of space for up to 6 guests, featuring a kitchen, air conditioning, and a terrace, with a shared outdoor pool and fitness center on-site, and scuba diving and ecotours available nearby.
This pet-friendly hotel offers 1042 sq. ft. of space for up to 6 guests, featuring a kitchen, air conditioning, and a terrace, with a shared outdoor pool and fitness center on-site, and scuba diving and ecotours available nearby.

Islamorada, FL
10/16 – 10/17
$413/nightfor 1 night
Fisher Inn Resort & Marina
2 5hotel, Islamorada, Village of Islands
Hotel room listing in a 4-star luxury hotel. You will be based in Islamorada, Village of Islands.
Facilities and services include a child space, a food shop and a kitchen.
Facilities and services include a child space, a food shop and a kitchen.

Islamorada, FL
10/16 – 10/17
$1710/nightfor 1 night
Scenic Beachside Stroll At Our Breathtaking Resort | 3 Villa W/ Living Area
6 5hotel, Islamorada, Village of Islands
Located in Matecumbe, Islamorada, this hotel is just 0.3 miles from Hurricane Monument and Indian Key Historic State Park, offering a prime seaside location.
This pet-friendly hotel features 4 bedrooms, accommodating up to 12 guests with 950 sq. ft. villas including a kitchen, and access to a fitness center and shared pool, perfect for exploring nearby water activities.
This pet-friendly hotel features 4 bedrooms, accommodating up to 12 guests with 950 sq. ft. villas including a kitchen, and access to a fitness center and shared pool, perfect for exploring nearby water activities.

Islamorada, FL
10/16 – 10/17
$517/nightfor 1 night
Sands Of Islamorada
2 5hotel, Islamorada, Village of Islands
Located in Islamorada, Village of Islands, this hotel is 2 miles from Indian Key Historic State Park and 4 miles from Theater of the Sea.
This pet-friendly hotel offers rooms with free Wi-Fi, air conditioning, and a swimming pool, with some studios featuring a kitchenette and balcony, making it a great choice for travelers with pets.
This pet-friendly hotel offers rooms with free Wi-Fi, air conditioning, and a swimming pool, with some studios featuring a kitchenette and balcony, making it a great choice for travelers with pets.

Islamorada, FL
01/11 – 01/15
$436/nighttotal: $1744 (4 )
La Siesta Resort & Villas
1 2hotel, Islamorada, Village of Islands
La Siesta Resort & Villas is a pet-friendly hotel in Islamorada, Village of Islands, located directly on the ocean, 3.7 miles from Theater of the Sea and 6.7 miles from Anne's Beach.
Guests can enjoy a beachfront location with ocean views, an on-site marina, and complimentary non-motorized watersports, making it a perfect seaside escape for travelers with pets.
Guests can enjoy a beachfront location with ocean views, an on-site marina, and complimentary non-motorized watersports, making it a perfect seaside escape for travelers with pets.

Islamorada, FL
10/16 – 10/17
$1239/nightfor 1 night
Stunning Bay View Villa In Florida Keys | Beach Getaway W/ Scenic Outdoor Pool
2 5hotel, Islamorada, Village of Islands
Enjoy a beachfront location in Islamorada's Matecumbe neighborhood, just a short distance from the Keys History & Discovery Center and the History of Diving Museum.
This pet-friendly hotel offers 1042 sq. ft. villas with two bedrooms and a guest capacity of six, featuring a scenic outdoor pool and easy access to nearby scuba diving and snorkeling adventures.
This pet-friendly hotel offers 1042 sq. ft. villas with two bedrooms and a guest capacity of six, featuring a scenic outdoor pool and easy access to nearby scuba diving and snorkeling adventures.

Islamorada, FL
10/16 – 10/18
$457/nighttotal: $914 (2 )
Guest Room, 1 King: Resort W/ Marina And 3 Outdoor Pool | Free Parking
1 2hotel, Islamorada, Village of Islands
Enjoy a pet-friendly resort experience in Islamorada, Village of Islands, situated directly on 15 acres of oceanfront property, just a short distance from Windley Key Fossil Reef Geological State Park and Indian Key Historic State Park.
This hotel offers a true Keys experience with direct beach and marina access, three outdoor pools, on-site dining, and guided water sports excursions, making it an ideal choice for travelers seeking seaside adventures with their pets.
This hotel offers a true Keys experience with direct beach and marina access, three outdoor pools, on-site dining, and guided water sports excursions, making it an ideal choice for travelers seeking seaside adventures with their pets.

Islamorada, FL
10/16 – 10/17
$1215/nightfor 1 night
Experience Soothing Moments & 1brluxury! Free Parking, Onsite Pool, Pet-friendly
1 5hotel, Islamorada, Village of Islands
Located in Islamorada's Matecumbe neighborhood, this hotel is just steps from Indian Key Historic State Park and the Hurricane Monument.
This pet-friendly hotel offers a 1-bedroom luxury apartment with air conditioning, free parking, an onsite pool, and is close to water activities, making it ideal for travelers with pets.
This pet-friendly hotel offers a 1-bedroom luxury apartment with air conditioning, free parking, an onsite pool, and is close to water activities, making it ideal for travelers with pets.

Islamorada, FL
10/16 – 10/17
$2556/nightfor 1 night
Your Idyllic Getaway Awaits! Breathtaking Beachfront, Outdoor Pool | 3 Units
6 5hotel, Islamorada, Village of Islands
This hotel in Islamorada, Village of Islands, offers a beachfront location in the Matecumbe neighborhood, putting you within easy reach of landmarks like Hurricane Monument and Indian Key Historic State Park.
Enjoy a pet-friendly stay with 6 bedrooms and 3 bathrooms accommodating up to 18 guests, featuring air conditioning, internet, a garden, concierge, fitness center, and a shared outdoor pool, with each of the three 950 sq. ft units including a kitchen.
Enjoy a pet-friendly stay with 6 bedrooms and 3 bathrooms accommodating up to 18 guests, featuring air conditioning, internet, a garden, concierge, fitness center, and a shared outdoor pool, with each of the three 950 sq. ft units including a kitchen.










