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Pet-friendly vacation rentals in Summerland Key

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Popular amenities for Summerland Key pet-friendly home rentals

Pet-friendly house rentals

Superhost
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

KevinRating, 5 stars2 weeks ago
This place was fantastic, had 5 people, very comfortable. Pool was very close and very enjoyable. Everything was very clean and tidy. In a gated community, that was a bonus. No matter where you want to go it isn’t more than 15 min tops. There are a few good restaurants on Stock island, the rest you only have to go a few miles. Very good place to stay.
Guest favorite
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

HayleyRating, 5 stars3 months ago
Fantastic location and lovely house.
Guest favorite
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

DaveRating, 5 stars1 month ago
Incredible property. Perfect gathering space for my entire family of 6. Private yet close to commerce like Publix and local gym to work out. Great memories made.
Guest favorite
Home in Key Colony Beach
4.94 out of 5 average rating, 49 reviews

Waterfront House - 30' Dock & Pool & Cabana Club

LauraRating, 5 stars1 month ago
We will be back! We loved it! Clean, comfortable with lots of room. We loved being able to keep our boat behind the house and the trailer in the driveway. We loved walking around Keys Colony. The Cabana Club and Sparkys Restaurant were both within walking distance. The kitchen had every gadget you could imagine. The dining table was perfect for dinners and card playing. The beds were comfy. No allergies whatsoever! Thank you so much!!
Guest favorite
Home in Key Colony Beach
4.94 out of 5 average rating, 106 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

BillRating, 5 stars1 month ago
the home was spotless. modern and up to date. Quiet area and street. includes access to a beach club down the street. restaurants and shops nearby. my wife enjoyed the fresh seafood. it's a 10
Guest favorite
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

BonniRating, 5 stars3 weeks ago
Jose was a very responsive host and we appreciated his communication. The house matches the description well and was very clean upon arrival. The location is off the main highway, which is great, but is across from the back of the post office distribution center so can be a little noisy at times. It is quite walkable to the grocery store and some restaurants/ shops. We also brought our 2 dogs (with permission of the owner) and the yard is very well set up for that as it is fully fenced in, except for the dock area.
Guest favorite
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

BretRating, 5 stars1 week ago
We loved our stay at the beach house! It was exactly what we were looking for. Very peaceful and right on the beach. The house was exactly like what the pictures showed. Tom was very friendly and helpful with anything we needed. We will probably stay there again in the future.
Guest favorite
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

AnneRating, 5 stars3 weeks ago
Looks just like the photo’s. Unfortunately weather was a little chilly the first couple of days. When it warmed up we enjoyed the local cabana club with the heated pool, beach and restaurants. The accommodations were spacious and clean.

Pet-friendly home rentals with a pool

Superhost
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

MaureenRating, 5 stars10 months ago
What a great find! Everything we needed was there! Quick walk to everywhere: beach, Duval street fun, restaurants and grocery store. So glad we went with this air bnb and not the hotel we normally go to. Saved so much money. Loved the privacy!
Superhost
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

JoshuaRating, 5 stars3 months ago
We were looking for a great place close to a small beach, an ocean view, which was clean and could house our family comfortably. This place did that and provided a place away from tourist crowds. Very nice place
Superhost
Home in Marathon
4.92 out of 5 average rating, 66 reviews

Oceanfront mermaid house pool and dock

PatriciaRating, 5 stars2 weeks ago
Greg's place was amazing! I loved being outside, sitting by the water, and looking out at the beautiful view. It is very quiet and peaceful, you feel like you are the only people around. We loved looking for sealife from the dock, and watching the boats go by the canal. The living room was comfortable and clean, and made a cozy place to enjoy the evenings. It was especially nice to have both bedrooms with their own ensuite bathrooms, and suited our two couples perfectly. I would stay here again in a heartbeat!
Superhost
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

JayRating, 5 stars15 months ago
We all loved the house. Plenty of space, the outdoor patios were a daily hangout, the views were great, what's not to love. The maintenance of the house itself was excellent and it didn't feel like a "rental". Well decorated, not worn down, a bathroom for everyone, it was great. We rented a golf cart to get back and forth from town which was very easy and barely a ten minute drive. We did have a small issue with the pool while there, which apparently is very unusual. It is Key West so it took a few days to get the parts needed. However, Javier was always easy to reach and while he did eventually fix it it was his 'out of the box' thinking and communication on everything that was superbly professional. I understand he manages several properties and we would gladly stay at any of them. With an AirBNB, if something goes wrong and you're far from home all you have to rely on is the owner/manager and you are in excellent hands with Javier. A++ on customer service
Superhost
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

JasonRating, 5 stars4 weeks ago
Roy was very responsive and helpful. He showed up immediately when we had a problem with the internet router and it was fixed right away. The gated community helped us feel secure. we will stay there again!!
Guest favorite
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

AmandaRating, 5 stars2 days ago
I just finished a 5 week stay at Michael’s place and have nothing but good things to say about the property. I loved the location because it is close to the ocean and is great for those who love to bike and walk. The condo is clean, comfortable, and has everything needed for preparing meals. I worked from the property and never had any issue with Wi-Fi. The heated pool is a big bonus. I hope to stay again.
Guest favorite
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

AustinRating, 5 stars7 months ago
We stayed here for a whole week and it was very awesome everything way exceeded our standards and we cant wait to come back!
Guest favorite
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

ShannonRating, 5 stars1 month ago
This was my second time staying at gulf coast oasis, and it was amazing again. You can tell that the owners take great care of the house and property, and they are super responsive and reach out proactively. It’s a fantastic location in Marathon which is central to restaurants and local activities. The house itself is stocked with everything you need to feel at home. It’s secluded/fully fenced, has tons of amenities (heated pool, putting green, kayaks, bikes, grill, fire pit, comfy indoor and outdoor seating). The kitchen is stocked with everything you need like a Keurig and kcups, pans and gadgets and utensils for cooking, loads of spices. Memory foam beds are comfy. They have extra little touches throughout like toiletries, games, fans, tons of beach towels, pool toys. We saw manatees in the canal, birds and lizards around the property. I can’t say enough good things about this house. My group included 2 couples and 2 dogs. We were comfortable, relaxed, and had a fun stay.

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

LilianaRating, 5 stars13 months ago
We had the perfect vacation! Love the location and the amenities of Key Colony Beach. The place was great for relaxing. I only wish we brought our dog..
Guest favorite
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!

KristinRating, 5 stars1 week ago
Quiet, private, clean, close to everything, and great ambience. The hot tub was amazing. Highly recommend.
Guest favorite
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

AngelaRating, 5 stars2 months ago
Amazing views from the house. Right on the water. The water is clear and calm, easy to paddle board and kayak. Great sunrises and sunsets. The best view of the sunset was from the kayaks while on the water. All the bedrooms had water views. Plenty of linens. The house was very clean. We enjoyed the cabana club a couple of days. That was a nice addition- warm pool and a sandy beach.
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

LyndseyRating, 5 stars20 months ago
House was beautiful with a large enough dock for us to bring our boat! Great location for fishing and exploring the Keys! Highly recommend!
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

JennyRating, 5 stars4 months ago
Our stay at 728 Passover Ln. was amazing. Cannot even explain how breathtaking the pool and sitting area is and the walking path🫶🏻the outdoor shower adds a great element house was plenty big was just two of us, but could’ve definitely handled four with no issues at all was well stocked, very clean.
Superhost
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

JayRating, 5 stars1 week ago
The location is great. All top sights and restaurants are walkable. Joe was very responsive. We would definitely stay again!
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

HayleyRating, 5 stars8 months ago
Just want to write an updated review since most of these are older. The previous reviews about the house AC being hot in the downstairs bedrooms has been fixed. The house has two brand new AC units. House was immaculate and in the perfect location with all the amenities you’d need. Only issue we ran into is the Wi-Fi does not work. They are actively working on it but the Sonos speakers did not work outside and the TVs were in and out. All in all this house had everything we needed and more
Superhost
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

JasonRating, 5 stars3 weeks ago
Great little place for 1 or a couple. Beautiful surroundings in Big Pine. 45 min drive to key west, 15 min drive Bahia Honda state park. If you’re looking for a peaceful spot surrounded by nature but still pretty close to some awesome keys attractions, this definitely fits the bill.

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

  • Total rentals

    130 properties

  • Nightly prices starting at

    $80 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