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Pet-friendly holiday rentals in Summerland Key

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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

Guest favourite

Home in Marathon

5 out of 5 average rating, 24 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.

Townhouse in Duck Key

4.85 out of 5 average rating, 160 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. ****

Guest favourite

Apartment in Key West

4.88 out of 5 average rating, 175 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).

Guest favourite

Guest house 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

Guest favourite

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.

Guest favourite

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.

Guest favourite

Home in Key Colony Beach

5 out of 5 average rating, 6 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**

Guest favourite

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.

Guest favourite

Flat 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.

Guest favourite

Home in Marathon

4.93 out of 5 average rating, 108 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 favourite

Home in Marathon

4.94 out of 5 average rating, 126 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

Home in Key West

4.88 out of 5 average rating, 51 reviews

Key West Paradise

Guest favourite

Home in Marathon

5 out of 5 average rating, 12 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

Guest favourite

Home in Key West

4.92 out of 5 average rating, 276 reviews

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

Guest favourite

Home in Key Colony Beach

4.94 out of 5 average rating, 49 reviews

Waterfront House - 30' Dock & Pool at Cabana Club

Guest favourite

Home in Key Colony Beach

4.94 out of 5 average rating, 106 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Guest favourite

Home in Marathon

4.98 out of 5 average rating, 47 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

Guest favourite

Home in Sugarloaf Key

4.8 out of 5 average rating, 103 reviews

Guest House - Sugarloaf Beach Key West

Guest favourite

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

Cottage in Key West

4.83 out of 5 average rating, 18 reviews

Colony Sunset- Bright and airy cottage

Home in Marathon

4.93 out of 5 average rating, 14 reviews

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

Home in Marathon

4.75 out of 5 average rating, 20 reviews

Sunset Views, Pool and Dock

Home in Key West

4.6 out of 5 average rating, 5 reviews

Coastal Comfort; Waterfront Luxury Home with priva

Townhouse in Key West

4.92 out of 5 average rating, 207 reviews

Spotlessly clean 3 bedroom/3 bathroom family home

Guest favourite

Home in Key Colony Beach

5 out of 5 average rating, 9 reviews

Key Colony Beach-POOL & DOCK

Guest favourite

Home in Marathon

4.88 out of 5 average rating, 16 reviews

Golf Coast Oasis

Home in Cudjoe Key

4.92 out of 5 average rating, 12 reviews

Blue Palms Retreat

Private, pet-friendly home rentals

Home in Key Colony Beach

4.78 out of 5 average rating, 18 reviews

2BR Oceanview Dog Friendly | Pool | Dock | Deck

Guest favourite

Home in Marathon

4.9 out of 5 average rating, 21 reviews

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

Home in Marathon

4.57 out of 5 average rating, 7 reviews

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

Townhouse in Key West

4.8 out of 5 average rating, 59 reviews

Location Location Beach Paradise in the Keys Duval

Home in Key West

4.68 out of 5 average rating, 63 reviews

Poolside Paradise | Heated Pool, Steps to Duval St

Flat in Big Pine Key

4.78 out of 5 average rating, 32 reviews

Apartment in Big Pine

Cabin in Key West

4.72 out of 5 average rating, 88 reviews

Rustic 4BR Dog Friendly | Hot Tub | Deck

Guest favourite

Home in Marathon

4.94 out of 5 average rating, 18 reviews

Gulf side Gem, 45 ft. dock, pool, Hot tub and more

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

Total rentals
130 properties
Nightly prices starting at
₹6,929 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