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Pet-friendly vacation rentals in Summerland Key

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Summerland Key

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Home in Key Colony Beach

4.73 out of 5 average rating, 133 reviews

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach

NEW VACATION RENTAL. Completely renovated. Open floorplan. New kitchen and bathrooms. New furnishings. Beautiful water views. Game room with pool table. DOGS PERMITTED ($250 FEE PER DOG, 1- 2). YOU MUST TELL ME IF YOU WANT TO BRING A DOG WHEN YOU SUBMIT YOUR REQUEST. Yard with Tiki. Enjoy meals, drinks or shady relaxation. 35 feet of dockage. Cabana Beach and Pool Club included. MUST SIGN KCB AND HOUSE RULES DOCUMENTS WITHIN 48 HOURS OF BOOKING AGE 25 OR OLDER TO BOOK PLEASE

A heated pool is framed by two thatched umbrellas, offering shade and relaxation. Surrounding the pool are several wooden lounge chairs, inviting comfort in the sun. Lush greenery is visible in the background, enhancing the serene ambiance of the outdoor space.

Home in Marathon

5 out of 5 average rating, 26 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

A contemporary living space features a blue sofa adorned with decorative pillows and a unique wooden coffee table. The dining area includes a round table with black chairs, while the kitchen is visible in the background, equipped with modern appliances and natural light streaming in through the windows.

Townhouse in Duck Key

4.85 out of 5 average rating, 161 reviews

Vibrant Beachfront Villa

Welcome to Beachfront Villa that has recently been renovated. The 2 bedroom 1.5 bath luxury villa is located in the popular area of Duck key alongside of Hawks Cay Resort. Duck Key marina is located across the street where you can dock your boat or charter a boat for the day. Enjoy stunning sunset views from the back porch. Kitchen includes all amenities including silverware ,plates , cups , and pots. Linens and towels provided. *** Pets welcome with host approval and pet fee. ****

A spacious living area features a light blue couch paired with a white coffee table. A dining table with multiple chairs is visible, and artwork depicting marine life adorns the walls. Natural light enhances the wood flooring and creates an inviting space.

Condo in Key West

4.88 out of 5 average rating, 176 reviews

Spacious Updated Waterfront Condo, 2/2 Pool, Dock

Time to relax! Bring your family & friends to this 1350 sqft Waterfront condo home. Boat slips available on site with commercial ice machine, fish cleaning station and BBQ grills. Located in historic Downtown Key West. Walk/Bike everywhere 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grill, bike rentals, parking, secure keyless entry, & private elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

A sandy outdoor space features a lounge chair and a kayak resting among palm trees. A hammock is suspended between two trees, with ocean views visible in the background. The area has scattered stones and greenery, enhancing the natural setting.

Guesthouse in Marathon

4.94 out of 5 average rating, 18 reviews

The Pink Dolphin House.

Weekly rental only. Saturday to Saturday. Relax with the whole family at this peaceful home with beautiful views. Ocean front Duplex shared with the owners, this quiet neighborhood is an ocean lovers dream. The Jetty offers tranquility, sunshine and sea. Drink your morning coffee there as you plan you day. Bring man’s best friend and enjoy the water. Paddle boarding and kayaking awaits you oceanside. A pool, and an outside patio area/dining room with a gas grill

Home in Marathon

4.86 out of 5 average rating, 22 reviews

Pet Friendly Half-Duplex Cottage w/40' Slip Option

We have a lovely oceanside cottage in Marathon Key, Florida, close to everything with many amenities. The cottage has a large yard and plenty of room to park boats, RVs, and wave runners. This modernized cottage is for you if you all need a great place to stay. This quaint and cozy home offers good value and features new furniture and brand-new state-of-the-art stainless steel appliances. There is one bedroom and a pull-out queen-size sofa bed.

A spacious bedroom features a comfortable bed draped in striped bedding. Sliding glass doors provide access to the outdoors, while a large flat-screen TV is mounted on the wall. A floor lamp and a decorative piece enhance the room's inviting layout.

Home in Marathon

4.96 out of 5 average rating, 26 reviews

Waterfront w/pool and hot tub

Professionally decorated, spacious, canal view keys home located in Key Colony Beach, the “Gem” of the Florida Keys. Featuring 2BR 2BA accommodating up to 6 ppl in a large & open living room & backyard, provided w/2 bikes, 2kayaks, grill, and 2 minutes walk to Sunset park, it is the perfect Florida Keys getaway for your family. This location is in the heart of the Florida Keys only 45 minutes from Key West and 35 minutes to Islamorada.

Home in Key Colony Beach

5 out of 5 average rating, 7 reviews

Paradise Cove!30ft Dock Pool BBQ

Our stunning new property located in the heart of the Florida Keys in Key Colony Beach! This exquisite retreat offers everything you could ever dream of for a perfect getaway – from a heated pool and breathtaking water views to a private dock for your boat! Step into luxury as you enter our meticulously designed home, where every detail has been crafted to create the perfect haven for relaxation and adventure. **Small Pets Only**

Home in Key West

4.92 out of 5 average rating, 26 reviews

Poinciana Treetop ~ Casual Second Floor Duplex

Vacation near historic Duval Street with parking and a treetop view. Or vacation with friends by renting both floors of this duplex. This conveniently located home allows you to have plenty of fun and enjoy a respite in your own private space. THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished second-floor duplex home comes with Key West charm and contemporary touches.

A spacious living area is visible, featuring comfortable seating and a dining area with counter stools. Large windows allow natural light to illuminate the room. Various artworks adorn the walls, adding visual interest to the neutral-toned space.

Apartment in Key West

4.85 out of 5 average rating, 41 reviews

Castaway Cove: Pet-friendly 2/2 condo near beach!

Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching.

The exterior of a blue house is surrounded by a landscaped garden featuring palm trees and other greenery. A gravel driveway leads to the entrance, providing ample space for parking. The sky is clear and sunny, enhancing the inviting atmosphere of the property.

Home in Marathon

4.93 out of 5 average rating, 109 reviews

Beautiful Renovated Home in Marathon, FL

Cozy home centrally located in the heart of Marathon with a ton of parking space for a boat or RV... Stay at ease in this family friendly neighborhood with lots of fun nearby (within 10 minutes) such as Sombrero Beach, FL Keys Aquarium, public boat ramp, kayaking, diving, restaurants and more!!! Licensed and inspected by the City of Marathon, Lic.#VACA-21-409

Home in Marathon

4.94 out of 5 average rating, 127 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

House suits multiple families with kids, groups of couples, small and large families, or solos. Home is easy to get to, easy to get inside and the neighborhood is very peaceful. Plenty to do around the island or on the water. 5 large bedrooms and 3 large bathrooms with an open living room and a fully stocked kitchen. We look forward to hosting you.

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Popular amenities for Summerland Key pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

A covered porch features a cozy seating area with a patterned couch, inviting relaxation. Lush greenery surrounds the space, including palm trees and shrubbery. A ceiling fan provides airflow, while natural light brightens the area, creating a welcoming spot for enjoying the outdoors.

Home in Key West

4.88 out of 5 average rating, 52 reviews

Key West Paradise

A bedroom features neutral-colored walls and tiled flooring. A queen bed with a blue and white patterned blanket is positioned against the wall. Two windows allow ambient light, and a nightstand with a lamp sits beside the bed. A door leads to a bathroom area.

Home in Marathon

4.82 out of 5 average rating, 22 reviews

Dock Pool Ramp Jacuzzi Ocean Views Kayaks

A well-lit bedroom features a spacious bed dressed in white linens. Decorative pillows add color, while a light blue accent wall enhances the calming atmosphere. Large windows bring in natural light and offer views of the surrounding water, complemented by a ceiling fan and bedside lamp.

Home in Marathon

5 out of 5 average rating, 12 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

Home in Key Colony Beach

4.94 out of 5 average rating, 49 reviews

Waterfront House - 30' Dock & Pool & Cabana Club

Home in Key Colony Beach

4.94 out of 5 average rating, 106 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

This master bedroom features a spacious bed covered with a quilt and a cozy seating area with a sofa. Large windows allow for natural light and views of the outdoors while the wood paneled ceiling adds warmth to the room.

Home in Marathon

4.98 out of 5 average rating, 47 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

A private beach scene features four adirondack chairs in white and turquoise, positioned in soft, sandy areas under palm trees. The calm ocean extends to the horizon, with a distant dock visible on the water. Bright clouds hover in a blue sky.

Home in Sugarloaf Key

4.8 out of 5 average rating, 104 reviews

The Guest House - Sugarloaf Beach Key West

A canal dock extends alongside the property, featuring wooden decking and a swimming ladder for easy access to the water. Lounge chairs are positioned nearby, and tall palm trees provide a tropical ambiance. The clear blue sky reflects off the tranquil water.

Home in Key Colony Beach

4.92 out of 5 average rating, 132 reviews

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

Pet-friendly home rentals with a pool

The living area features a gray sofa complemented by a colorful area rug. A flat-screen television is mounted on the wall. A small bar with seating connects to the kitchen area, adorned with bamboo window treatments, enhancing the bright and airy ambiance.

Cottage in Key West

4.83 out of 5 average rating, 18 reviews

Colony Sunset- Bright and airy cottage

A light-filled living area features a spacious gray sofa adorned with blue cushions. A tropical-inspired ceiling fan hangs above. Large glass doors open to a scenic view, complemented by a cozy rug and a wooden table with chairs, creating an inviting space for relaxation.

Home in Marathon

4.93 out of 5 average rating, 14 reviews

Pool & Spa, Walk to Beach, Dock, Tiki, Lux Home

Home in Marathon

4.92 out of 5 average rating, 66 reviews

Oceanfront mermaid house pool and dock

A wide, covered porch features a wooden floor and white railing, with several chairs positioned to face expansive waterfront views. Lush greenery and distant boats can be seen in the serene water, providing a calm and inviting outdoor space.

Home in Key West

4.6 out of 5 average rating, 5 reviews

Coastal Comfort; Waterfront Luxury Home with priva

A welcoming porch features two rocking chairs, one in bright blue and the other in red. Natural light filters through, illuminating the wooden deck, framed by lush greenery. Glass double doors provide access to the interior space, enhancing the open and airy feel.

Townhouse in Key West

4.92 out of 5 average rating, 208 reviews

Spotlessly clean 3 bedroom/3 bathroom family home

A lagoon-shaped pool is surrounded by lush tropical foliage, providing a serene setting. Sun loungers are placed near the water, and a gazebo offers shade. The sky is clear, with a few scattered clouds, enhancing the tranquil atmosphere.

Apartment in Key West

4.91 out of 5 average rating, 87 reviews

Comfy 2/2 pool/gym/tennis/hottub

An aerial view of a vibrant waterfront neighborhood showcases a pale yellow house surrounded by lush greenery. Nearby, several homes with varying colors and styles line the streets, while a deep canal runs at the back, providing easy waterway access.

Home in Key Colony Beach

5 out of 5 average rating, 9 reviews

Key Colony Beach-POOL & DOCK

A spacious living area features a large gray sectional sofa adorned with decorative cushions. A round coffee table is positioned in front, and a colorful painting of a boat enhances the wall. Natural light streams in through glass doors leading to an outdoor seating area.

Home in Marathon

4.88 out of 5 average rating, 16 reviews

Golf Coast Oasis

Private, pet-friendly home rentals

A well-maintained outdoor area features a round table surrounded by white chairs. Lounge chairs with green cushions are positioned nearby, under teal umbrellas. A white picket fence borders the area, providing views of the water beyond.

Home in Key Colony Beach

4.78 out of 5 average rating, 18 reviews

2BR Oceanview Dog Friendly | Pool | Dock | Deck

An outdoor space features a private spa surrounded by tropical greenery. A comfortable sofa and a small table sit under an umbrella, while a planter adds a touch of nature. The area is enclosed by a white fence, providing privacy and a serene environment.

Apartment in Key West

4.95 out of 5 average rating, 303 reviews

Honeymoon Hideaway, King bed, Private Deck & Spa!

A spacious bedroom is highlighted by a comfortable wooden bed with patterned linens. A bedside lamp casts a warm glow. Floor-to-ceiling windows offer views of the beach, with outdoor seating visible on the patio. Tropical decor adds a subtle touch of elegance.

Home in Marathon

4.9 out of 5 average rating, 21 reviews

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club

A stylish bedroom features a spacious bed dressed in blue linens, flanked by matching nightstands with lamps. An area rug with a geometric pattern covers the floor. Natural light enters through sliding glass doors, which open to a balcony with views of the pool.

Home in Marathon

4.57 out of 5 average rating, 7 reviews

Martin`s Beach House Coco Plum Dream on Avenue G 4

A charming cottage facade is framed by lush greenery, featuring a welcoming porch with two blue chairs. Sunlight casts playful shadows on the wooden deck, highlighting the entrance with a potted plant nearby. The home exudes a relaxed, tropical vibe.

Home in Key West

4.85 out of 5 average rating, 85 reviews

Centrally located 2BR Dog Friendly | Pool | Deck

A bright and inviting exterior view captures the charming two-story townhome nestled among tropical foliage. A white picket fence surrounds the property, and the entrance features double doors flanked by decorative plants. Sunlight bathes the scene, enhancing the serene outdoor environment.

Townhouse in Key West

4.8 out of 5 average rating, 60 reviews

Location Location Beach Paradise in the Keys Duval

A landscaped outdoor area is showcased, featuring an inviting lawn bordered by tropical plants. Two colorful cornhole boards are positioned on the lawn, and a path of paving stones leads to the side of the home, enhancing the outdoor space.

Home in Marathon

4.58 out of 5 average rating, 12 reviews

Walk to Beach 4BR | Dock | Dog Friendly | Pools

A spacious room features a bed draped in a blue and white floral bedding set. Large windows offer views of the outdoors, with a small dining table and chairs visible on the balcony. A compact refrigerator is positioned near the entrance, enhancing convenience.

Apartment in Big Pine Key

4.79 out of 5 average rating, 33 reviews

Apartment in Big Pine

Quick stats about vacation rentals that are pet-friendly in Summerland Key

Total rentals
130 properties
Nightly prices starting at
R1,469 ZAR before taxes and fees
Total number of reviews
950 reviews
Family-friendly rentals
90 properties are a good fit for families
Rentals with a pool
90 properties have a pool
Rentals with dedicated workspaces
40 properties have a dedicated workspace

Destinations to explore