Pet-friendly holiday rentals in Cudjoe Key

Tiny home in Big Pine Key

A serene beach scene captures soft sands meeting clear waters under a bright blue sky. Lush palm trees frame the view, while visitors are seen enjoying the tranquil coastline and gentle waves. Green foliage and distant beach cabanas are also visible, enhancing the natural beauty.

4.88 out of 5 average rating, 129 reviews

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!

WalkabilityPetsAccuracy

Tiny home in Summerland Key

4.94 out of 5 average rating, 77 reviews

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.

PetsOutdoor spacesView

A wooden sign displaying the word 'paradise' is mounted above a window. The letters are painted in a mix of colors, with a weathered finish. Soft sunlight filters through the white blinds, casting gentle shadows on the wall.

4.96 out of 5 average rating, 26 reviews

Island Paradise

*** Please note: There is a one time registration fee of $125 to be paid at gate*** Cozy keys getaway w/ ocean front heated pool, boat ramp and more. Relax in this 1 BR, 1 BA manufactured home in a resort style park with heated pool, hot tub, boat ramp, sports courts and walkable dining. This clean well kept home features a king bed in primary BR and queen gel memory foam pullout sofa in living room. Fully stocked kitchen! Hair dryer, shampoo, conditioner, bath soap, etc. are furnished.

WalkabilityOutdoor spacesCleanliness

4.94 out of 5 average rating, 18 reviews

Dolphin Daydreams at Venture Out

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** DOLPHIN DAYDREAMS is a freshly built 2-bedroom tropical home specifically designed to be the perfect antidote to the stresses of everyday life. Substitute zoom meetings and rush hour traffic for slow mornings on the patio and afternoons in the sun. Nestled within Venture Out, a popular resort community on Cudjoe

PetsSleep qualityBathroom

4.93 out of 5 average rating, 96 reviews

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!

WalkabilityPetsHot tub

4.97 out of 5 average rating, 36 reviews

An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.

Condo in Summerland Key

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 spacesCheck-in

A tropical backyard features a private saltwater pool surrounded by seating areas. A thatched-roof Tiki Hut is adorned with string lights. A gas fire pit sits centrally, while walls are embellished with colorful fish murals. Lush greenery completes this inviting outdoor space.

4.91 out of 5 average rating, 116 reviews

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 spacesCheck-in

Cottage in Little Torch Key

A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.

4.89 out of 5 average rating, 183 reviews

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!

PetsWalkabilityBeach

4.97 out of 5 average rating, 33 reviews

Home in Summerland Key

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 spacesWalkabilityFamily

An aerial view captures a vibrant community of stilt homes nestled along the coastline, with clear blue waters stretching in the background. Lush palm trees dot the landscape, while a distinctive red marker indicates a specific location within this scenic setting.

4.84 out of 5 average rating, 126 reviews

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***

PetsOutdoor spacesBeach

4.86 out of 5 average rating, 602 reviews

Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.

Villa in Marathon

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!

Outdoor spacesPetsParks

A private outdoor area features a hot tub surrounded by tropical foliage. A dining table with chairs is situated nearby on a wooden deck, offering shade from the overhead structure and a relaxing atmosphere for outdoor meals.

4.88 out of 5 average rating, 121 reviews

Near Duval: Hot Tub, Sleeps 6, Top Location

Just 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bedrooms, one bathroom, a full kitchen, and private outdoor perks—like a hot tub, second-story sundeck, and outdoor shower—you’ll have everything you need to relax in paradise. Ideal for up to 6 guests, it’s a tropical haven steps from world-class dining, shopping, and beaches. Book now and soak up the island life! Don’t forget to click the ♥ to save it for later.

Outdoor spacesWalkabilitySleep quality

Popular amenities for Cudjoe Key pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A bright living area is showcased with a sectional sofa and a round coffee table. Natural light fills the space, highlighted by decorative lamps and greenery visible through the windows. A woven rug adds texture to the wooden floor, contributing to a relaxed atmosphere.

4.96 out of 5 average rating, 56 reviews

Private Gated Cottage | Hot Tub | Pet Friendly

PetsWalkabilityFamily

4.6 out of 5 average rating, 5 reviews

Blue Heaven Marathon

Outdoor spacesParkingCleanliness

An outdoor area features a fenced pool surrounded by colorful chairs. Palm trees provide shade, and the spacious deck above is visible. The setting reflects a relaxed atmosphere with nearby greenery enhancing the tranquil environment.

4.85 out of 5 average rating, 34 reviews

Soothing Nest

Outdoor spacesWalkabilityAccuracy

A serene waterway is shown, flanked by palm trees and waterfront homes. A boat is seen navigating the calm waters, with clear skies enhancing the tranquil scene. The reflection of the surroundings is visible on the surface, creating a peaceful atmosphere.

4.64 out of 5 average rating, 185 reviews

Ocean Front Home in Great Location

PetsOutdoor spacesAccuracy

4.77 out of 5 average rating, 13 reviews

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

Outdoor spacesPetsHeating

5 out of 5 average rating, 5 reviews

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

WalkabilityOutdoor spacesDecor

5 out of 5 average rating, 4 reviews

Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.

LocationKitchenView

The outdoor swimming pool features a circular design surrounded by tropical palm trees and lounge chairs. Bright blue umbrellas provide shade for guests, while the clear blue sky enhances the vibrant atmosphere of the gated community.

4.94 out of 5 average rating, 154 reviews

Paradise found

PetsWalkabilityBeach

Pet-friendly home rentals with a pool

An expansive outdoor space is dotted with tropical palm trees and soft sand. A thatched tiki hut offers shaded seating, featuring a large outdoor TV. Game areas for volleyball and colorful outdoor games are visible, providing opportunities for relaxation and entertainment by the ocean.

5 out of 5 average rating, 7 reviews

Paradise Point - Oceanfront Luxury w/ Pool & Dock

Outdoor spacesIndoor spacesLocation

An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.

5 out of 5 average rating, 78 reviews

Tropical Keys Retreat | Pool | Hot Tub | Cinema

WalkabilityPetsCheck-in

4.97 out of 5 average rating, 33 reviews

An aerial view showcases a private dock with a boat alongside a heated pool. Lounge chairs are positioned near the pool, complemented by vibrant palm trees and neatly arranged outdoor furniture. The tranquil waters reflect the bright surroundings, enhancing the overall relaxing atmosphere.

Home in Key Colony Beach

Paradise Cove! 50ft Dock Pool BBQ

WalkabilityOutdoor spacesPool

4.95 out of 5 average rating, 161 reviews

A private heated pool is surrounded by a spacious patio with laid brick flooring. Palm trees frame the scene, while a vibrant sunset casts warm colors across the sky. Lounge chairs are positioned by the pool, inviting relaxation by the serene water view.

Villa in Marathon

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Outdoor spacesWalkabilityDecor

4.93 out of 5 average rating, 75 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

WalkabilityPetsParking

4.91 out of 5 average rating, 11 reviews

Villa Mars In Marathon

PetsOutdoor spacesNearby

Casa particular in Summerland Key

5 out of 5 average rating, 9 reviews

The Retiro House

Outdoor spacesValueCleanliness

A well-maintained two-story house features light-colored siding and contrasting blue shutters. A spacious, welcoming front porch is framed by tropical plants and neatly arranged landscaping. Steps lead up to the front door, providing easy access to the entrance.

5 out of 5 average rating, 39 reviews

Casa Calypso 3bed3bath sleeps 8 beautiful decorate

WalkabilityPetsKitchen

Private, pet-friendly home rentals

4.83 out of 5 average rating, 60 reviews

A single kayak glides through a serene mangrove tunnel, surrounded by lush greenery. The still water reflects the vibrant foliage above, creating a calming atmosphere. The branches arch gracefully overhead, providing a sense of enclosure in this natural waterway.

Houseboat in Marathon

Adventurers escape breathtaking off-grid houseboat

Outdoor spacesWalkabilityParking

4.76 out of 5 average rating, 141 reviews

Houseboat in Marathon

Tiny Home Aqua Lodges 2/1

PetsWalkabilityView

A view from beneath a thatched roof, showcasing calm waters and a gentle shoreline. Palm trees sway in the breeze, with a wooden dock extending towards the ocean. The sky features soft clouds during sunset, creating a peaceful atmosphere.

4.88 out of 5 average rating, 77 reviews

Oceanfront mermaid house pool and dock

PetsWalkabilityPool

A serene waterfront scene captures colorful sunset hues reflecting off calm waters. Palm trees sway gently in the breeze, while boats are moored along the canal. The peaceful atmosphere of the neighborhood is evident in the backdrop of charming docks and nearby structures.

4.92 out of 5 average rating, 78 reviews

Blue Ocean-AUGUSTSummer Deals AVAIL.

WalkabilityOutdoor spacesBathroom

4.88 out of 5 average rating, 68 reviews

Boat in Key West

Houseboat in Key West

Outdoor spacesPetsKitchen

5 out of 5 average rating, 5 reviews

Home in Key Colony Beach

Entire private two family water front home.

Outdoor spacesIndoor spacesPool

4.93 out of 5 average rating, 73 reviews

Two outdoor sun loungers are positioned on a concrete patio, facing a tranquil waterfront scene. A stunning sunset casts warm hues over the water, with boats visible in the distance. Wooden pilings line the dock, enhancing the idyllic setting.

Home in Key Colony Beach

Water, Water Everywhere! "The Wheel House"

WalkabilityOutdoor spacesCheck-in