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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Guest favorite

Home in Key West

4.95 out of 5 average rating, 308 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Guest favorite

Condo in Key West

4.84 out of 5 average rating, 149 reviews

2/2 Fully Updated Old Town Waterfront Corner Condo

Time to relax! Bring your family & friends to this fully updated 1350sqft Waterfront corner 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)

Guest favorite

Villa in Marathon

4.95 out of 5 average rating, 123 reviews

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

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

Guest favorite

Townhouse in Marathon

4.97 out of 5 average rating, 126 reviews

Boater’s Paradise 3br/2.5ba at Coral Lagoon

*PLEASE NOTE* slips for all Villas are under construction and not available. Pls inquire before booking!! Spectacular PET FRIENDLY 3 bed/2.5 bath 1350sf villa in beautiful Coral Lagoon, complete with a 40 foot wet slip and all the amenities! Spread out and enjoy the spacious, clean interior with free high speed wifi. Step outside to your boat and enjoy all the Gulf and Atlantic have to offer - both easily accessible in minutes. Relax with a drink at the pool after a long day of fun in the sun.

Superhost

Tiny home in Big Pine Key

4.86 out of 5 average rating, 135 reviews

Cheerful Tiny House in the Florida Keys

Enjoy your trip to the keys by staying at this wonderful tiny house, surrounded by nature and deers! This is a hidden gem in the keys for your relaxation, enjoyment. Cozy and roomy space for the whole family! The Tiny house is located in the small Breezy Pines RV Resort. It has everything you would need during your trip. Outdoor patio area with rattan sofa and armchairs, grill offer an additional comfort for incredible vacation! it has everything for your nice and comfy stay close to Key West!

Guest favorite

Home in Islamorada

4.97 out of 5 average rating, 178 reviews

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

Guest favorite

Cottage in Little Torch Key

4.9 out of 5 average rating, 156 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!

Guest favorite

Home in Key Colony Beach

4.94 out of 5 average rating, 101 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Superhost

Villa in Marathon

4.91 out of 5 average rating, 230 reviews

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!

Guest favorite

Home in Marathon

4.9 out of 5 average rating, 146 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

Guest favorite

Home in Marathon

4.9 out of 5 average rating, 105 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

Guest favorite

Home in Marathon

4.95 out of 5 average rating, 124 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.