
Pet-friendly holiday rentals in Sugarloaf Key
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Sugarloaf Key
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

Cottage 30 min from Key West, free parking, pool
Escape the everyday and unwind under the stars in this charming, nature-surrounded getaway where deer are frequent visitors. This cozy tiny house of offers 1 bedroom, 1 bathroom, and 3 beds, comfortably sleeping up to 4 guests. Enjoy peaceful surroundings, fresh air, and convenient double parking with space for a truck and boat trailer—perfect for outdoor adventures and total relaxation. Ideal for couples, families, or friends seeking quiet nights, wildlife views, and a simple, memorable stay!
PetsOutdoor spacesGetting around

Cottage
Experience island living at Sugarloaf RV Resort & Cottages in the Lower Keys, just 25 minutes from Key West. Our NEW Two-Bedroom Cottages sleep up to 6 guests with two queen beds and a full-size pull-out sofa. Enjoy a kitchenette with a double-burner stovetop, pots, pans, dorm fridge, microwave, K-Cup coffee maker, toaster, dishes, and utensils. Relax on your private patio and enjoy resort amenities including a heated / chilled pool, kayaks, paddle boards, bicycles, and a peaceful private lake.
Outdoor spacesPetsValue

Waterfront Condo Dock Pool Downtown Near Duval
Time to relax and vacation in this spacious 1,350 sq ft waterfront corner condo in downtown Key West. Bring your family and friends and enjoy a private balcony with marina views, full kitchen, and open living space. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Amenities include a heated pool, tiki area, BBQ grills, free parking, elevator access, and secure entry. Located about 1 mile from Duval Street and 10 minutes from EYW airport.
PetsOutdoor spacesBeach

Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks
Your Luxury Keys Getaway! Experience stunning Ocean views, amazing sunsets and sunrises, a 35' canal-front seawall, kayaks, bikes, outdoor shower, fish cleaning station & bait freezer. Everything you need to fully enjoy the Keys experience! Keep your boat at the house and be on the Atlantic or Gulf in minutes. Located halfway between Key West and Marathon, you get access to all resort amenities: heated pool, hot tub, pickleball courts, boat launch & store. Prime dates go fast, book now!
Outdoor spacesPetsValue

Tropical Paradise
Oceanfront home with private pool, boat dock, kayaks, and private beach Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24' boat allowed) screened in porch for dining There are 2 king bedrooms, 3rd bedroom has a queen with trundle 2 1/2 bath. This home has an open floor plan and recently remodeled kitchen.
Outdoor spacesKitchenWi-Fi

Tiki Time! Private Pool~Tiki Hut~Kayak~Grill!
Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a family vacation or relaxing getaway. Gorgeous 3BR home with your own private salt water pool, Tiki Hut, space to park a 30' boat/trailer, and ocean views from the balcony~Kayak, grill, beach toys await you for your beautiful day in the Florida Keys! Less than 5 min to Sombrero Beach, Dining & Local Bars! Experience the Florida Keys like a local and book Tiki Time today!
WalkabilityOutdoor spacesParks

Family Suite at Sugarloaf Key Hotel (Pet Friendly)
Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!
PetsOutdoor spacesNearby

Waterfront Cozy Cottage with Boat Ramp & Dock!
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!
PetsOutdoor spacesCleanliness

Starlight Serenity - Hideaway with Stunning Views
Escape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility. Book your next getaway for 3 nights or more!
Outdoor spacesPetsGetting around

Spanish Queen @Venture Out
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***
PetsWalkabilityBeach

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!
PetsOutdoor spacesWi-Fi

Oceanfront 2BR in Venture Out - 35’ Dock + Pool
Wake up to oceanfront sunrises in this 2BR/2BA coastal gem in Venture Out on Cudjoe Key. Enjoy turquoise water views, a 35’ seawall for boats up to 32’, and manatees gliding by. Fully equipped kitchen, private balconies, smart TVs, outdoor dining, grill, and more. Community perks include a heated pool, onsite store, tennis, pickleball and more. Just 20 mins to Key West! Pet friendly!. Gated entry, registration fee due at arrival.
WalkabilityHospitalityCondition
Popular amenities for Sugarloaf Key pet-friendly home rentals
Pet-friendly house rentals

Lennon's Lodge, Luxury Accommodations for up to 6!
Outdoor spacesPetsHot tub

Casa Calypso 3bed3bath sleeps 8 beautiful decorate
PetsWalkabilityBarbecue

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
ViewHospitalityNearby

Dolphin Daydreams at Venture Out
PetsLaundryBarbecue

Boat Dock! Tiki Beach Big Pine - 4 Bed
Outdoor spacesPetsHot tub

Island Paradise
WalkabilityOutdoor spacesAmenities

35’ dock/Completely Remodeled VO 366
Outdoor spacesWalkabilitySleep quality

Key West Paradise
Outdoor spacesPetsKitchen
Pet-friendly home rentals with a pool

Comfortable, clean, beautiful home in Key West
PetsWalkabilityComfort

Waterfront House with 37 ft Dock & Cabana Club
WalkabilityOutdoor spacesCheck-in

2Bd/1Ba Waterfront Retreat w/35’ Dock
Outdoor spacesWalkabilityBeach

Oceanfront Bungalow Venture Out
Outdoor spacesGetting aroundPool

Strictly Pleasure | Unique Yacht Stay in the Keys
WalkabilityFamilyKitchen

Waterfront Pool Home w/ 30’ Dock, Kayaks & Outdoor
Outdoor spacesSleep qualityLayout

KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK
WalkabilityPetsKitchen

Key West House
Outdoor spacesWalkabilityBathroom
Private, pet-friendly home rentals

Tiny Home Aqua Lodges 2/1
WalkabilityOutdoor spacesPool

Key West Outpost: eco-vacation
Outdoor spacesPetsValue

Private Gated Cottage | Hot Tub | Pet Friendly
PetsOutdoor spacesNearby

Gorgeous Ocean View Home!
PetsOutdoor spacesLocation

Love Shack: 2BR Houseboat w/ Decks & Views
Outdoor spacesGetting aroundAmenities

Blue Heaven Marathon
Outdoor spacesHospitalityFamily

Entire private two family water front home.
Outdoor spacesHospitalityPool

Sombrero Sunset-Marathon 7BR 6BA Waterfront Pool
WalkabilityOutdoor spacesComfort
Destinations to explore
- Miami Holiday rentals
- Four Corners Holiday rentals
- Miami Beach Holiday rentals
- Orlando Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Hollywood Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Cape Coral Holiday rentals
- Nassau Holiday rentals
- St. Petersburg Holiday rentals
- Rentals with a kayak Sugarloaf Key
- House rentals Sugarloaf Key
- Waterfront rentals Sugarloaf Key
- Rentals with beach access Sugarloaf Key
- Family-friendly rentals Sugarloaf Key
- Rentals with pools Sugarloaf Key
- Rentals with a hot tub Sugarloaf Key
- Pet-friendly rentals Monroe County
- Pet-friendly rentals Florida
- Pet-friendly rentals United States
- Sombrero Beach
- Smathers Beach
- Bahia Honda State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- Southernmost Point
- Florida Keys Aquarium Encounters
- Dolphin Research Center
- Key West Butterfly & Nature Conservatory
- Key West Lighthouse Museum
- Boca Grande Key
- Conch Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Curry Hammock State Park
- Key West Aquarium





