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Pet-friendly holiday rentals in Middleburg

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Middleburg

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

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Home in St. Augustine

4.82 out of 5 average rating, 110 reviews

Beach and Serenity house

Beautiful beach house! 6 blocks to beach, 2 blocks to intercoastal. Drive on to the beach at one end of the street, Easy walk to the best sunsets at the marsh Restaurants at each end of the street Up and downstairs screened in porches Back/front yard, all driveway access Quiet street for lots of R&R *PLEASE NOTE, AND THIS IS IMPORTNAT * We cannot split weekends. Friday and Saturday nights booked together *ONE PET PER STAY W/ APPROVAL *no washer/dryer available, hang dry only *STRICT OUT/IN TIMES

Guest favourite

Home in St. Augustine

4.95 out of 5 average rating, 132 reviews

St Augustine Hideaway! Relax minutes from Old town

The charm of St. Augustine while in your own oasis! A fully equipped home offers all the comforts you need for a relaxing stay. Convenient neighborhood just 3.5 miles north of historic downtown, this pet-friendly retreat features 3 bedrooms, 2 bathrooms, and accommodates up to 8 guests—making it perfect for family getaways. With a fully appointed kitchen, high-speed internet, smart TVs, a full-sized washer and dryer, and a home alarm system explore the beach or discover the city’s rich history.

Guest favourite

Condo in St. Augustine Beach

4.85 out of 5 average rating, 241 reviews

Ocean Side Complex w/ Heated Pool B-15

Great Condo in a Beach Side Community But just to be clear Beach Side does not mean Ocean Front you will not be able to see the Ocean from the Patio The Condo is located next to Shopping Restaurants, and Historic Downtown, Great Beaches for a relaxing stay and 2 pools 1 heated Year Round Must be 21 years old to rent IMPORTANT! This unit is DOG friendly. No other pets of any type are allowed. There is a $100 Pet Fee due when you book a reservation. I have to register them before you arrive

Guest favourite

Home in St. Augustine

4.89 out of 5 average rating, 335 reviews

Uptown Abode on Garnett- Dog Friendly!

Spacious 4 bedroom home in uptown St Aug w large porch and balcony attached to primary. Smart TV in living room & primary, large eat-in kitchen w Keurig & basic cooking supplies, washer & dryer. Perfect for large families or friend groups on vacation. 5 (+/-) minute drive to downtown historic St Augustine and conveniently located off of US-1 in cute neighborhood. Ample onsite parking is FREE! Charcoal grill available, bring your own charcoal and fluid! Dogs can stay for $35 with pre-approval.

Guest favourite

Home in St. Augustine

4.91 out of 5 average rating, 277 reviews

The Meadow House

"Ideal location near the beach, just minutes to drive or bike into historic downtown St Augustine. Bottom Unit is 1300 sq ft Coastal Farmhouse style with a open kitchen, dishwasher, garbage disposal, and large refrigerator with filtered water/ice maker, laundry room, private porch off master bedroom, fenced-in backyard, outdoor shower, and grill. House is 3 blocks from beach access/beach parking (if you choose not to walk). Rental and beach are pet friendly. Only 2 parking spots available.

Guest favourite

Home in Lincolnville

4.98 out of 5 average rating, 122 reviews

Southern Comfort - Downtown|Hot Tub|Heated Pool

The Southern Comfort is a 4BR/3.5BA home located right in the heart of Downtown St. Augustine on the famous King Street. High-end, designer touches will be found in all features of the home with respect to the 110+ year old character preserved in the 2020 renovation. Centrally located with a blend of privacy, convenience and a modern luxury design. Private, sparkling heated pool and hot tub with lounges perfect for lazy days by the water. #1 Vacation Rental in Downtown St. Augustine.

Guest favourite

Guesthouse in Beaches

4.99 out of 5 average rating, 185 reviews

Tropical guest house a few blocks from the beach

Take it easy at this unique and tranquil getaway. Private modern quest house located on lush tropical grounds behind main house. Includes: loft bedroom, full bath, kitchenette, wifi, air conditioning, private patio, and outdoor shower. Property is gated with parking. Walking distance to beach, bars, shops and restaurants. Hammock, volley ball, firepit, BBQ and bikes available upon request. Pets welcome. Fishing pier, boating, kayaking and golf options within a short distance.

Guest favourite

Holiday home in St. Augustine

4.98 out of 5 average rating, 118 reviews

1st Street Retreat, Dog Friendly Updated Apartment

Welcome to 1st Street Retreat a newly updated open concept dog friendly studio apartment, 1 block to beach, withing walking/bike riding distance to local restaurants. Keurig coffee machine. Free WIFI & TV, linens, towels, kitchen & bathroom amenities. Outside retreat has a private entrance, fenced in yard with dog run, outside shower, BBQ, table & chairs, propane fire pit. We also provide beach chairs, beach cart and beach towels. There is a pet fee of $100.00 we allow 2 dogs

Guest favourite

Apartment in St. Augustine

4.97 out of 5 average rating, 186 reviews

Dog-friendly, Walk Everywhere apt with FREE BIKES

Come stay in this completely renovated, beautiful second floor, pet-friendly one bedroom apartment with a large fully-equipped eat-in kitchen. A spacious balcony with rocking chairs. Shared use of the fabulous back yard with picnic tables, BBQ grills, and bicycles! One parking space guaranteed. Best part: The location! About a five-minute walk to historic downtown and Flagler. Super comfy queen size 4-post bed. Pet fee is $40 per dog per stay (max of 2 dogs).

Guest favourite

Home in Lincolnville

4.97 out of 5 average rating, 102 reviews

Art and sun filled home with hot tub in downtown.

Expansive garden surrounds this home built in the 1800s. Walking distance to everything St. Augustine has to offer. Two blocks from the best restaurant, cafe, and brewery in downtown. Large upper and lower porches let you relax and watch the horse drawn carriages pass by. The home is filled with antiques, artwork, and plants. Outdoor shower, grill, and hot tub encourage the ultimate vacation experience.

Guest favourite

Home in Riverside

4.96 out of 5 average rating, 114 reviews

2680- Sleeps 9, Riverside, Great Pet & Family Home

Must be min 25 yrs old. You will fall in love with this cozy renovated stylish home that is spacious and feels good. Plush beds, nice linens, and sound machines will put you in a sound sleep and give you all the rest you need after exploring the fun neighborhood of riverside. This home is fully fenced and walking distance to many bars, restaurants, shops, etc.

Guest favourite

Townhouse in Beaches

4.91 out of 5 average rating, 117 reviews

Mimi’s Beach Cottage in Jax Beach - Pets welcome!

Have fun with the whole family at this stylish townhome! The house is decorated to help you leave your worries at the door. And enjoy the peaceful and happy atmosphere in Jax Beach. Jax Beach is a hidden gem with clean, safe beaches! You will love the wide beach and tide pools!

Holiday rentals for every style

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Popular amenities for Middleburg pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in St. Augustine

4.81 out of 5 average rating, 116 reviews

Safe Haven, Unique two story carriage

Guest favourite

Home in St. Augustine

4.9 out of 5 average rating, 10 reviews

Old Town | Courtyard Fireplace | Dog Friendly

Guest favourite

Home in Jacksonville

4.8 out of 5 average rating, 44 reviews

~Colorful New Construction_Sleeps 10_Mayo Clinic~

Home in Jacksonville

4.84 out of 5 average rating, 32 reviews

Adorable Southside Bungalow

Guest favourite

Home in St. Augustine

4.88 out of 5 average rating, 128 reviews

The Beach House at Crescent Beach

Guest favourite

Home in St. Augustine

5 out of 5 average rating, 8 reviews

Beautiful St Andrews home w large lanai 212

Home in Southeast Jacksonville

4.69 out of 5 average rating, 29 reviews

Mandarin Pet Friendly Fenced in Yard Sleeps 8

Guest favourite

Home in Southeast Jacksonville

4.84 out of 5 average rating, 126 reviews

Mandarin Pearl. Close to everything.

Pet-friendly home rentals with a pool

Guest favourite

Home in Beaches

4.93 out of 5 average rating, 15 reviews

SMV Minigolf and Heated Pool

Home in Palm Coast

4.73 out of 5 average rating, 11 reviews

Hidden Oasis Spacious Pool Home with Florida Room

Home in Jacksonville

4.82 out of 5 average rating, 62 reviews

The House.Big privatePool.Quiet place.Pet Friendly

Guest favourite

Home in St. Augustine

5 out of 5 average rating, 136 reviews

Southern Charmer w/Pool - Walk to Everything!

Cottage in Elkton

4.88 out of 5 average rating, 106 reviews

Cottage w/pool on horse property, St. Augustine.

Home in Orange Park

4.84 out of 5 average rating, 164 reviews

Immaculate Home with Private Pool and Patio

Guest favourite

Home in Beaches

4.93 out of 5 average rating, 128 reviews

Renovated Beach Home w/ Heated Pool, Putting Green

Guest favourite

Guesthouse in Jacksonville

4.74 out of 5 average rating, 442 reviews

Pool House-2 Bdr/1Ba Apt-Pool-Sleeps 5-Pets OK

Private, pet-friendly home rentals

Guest favourite

Home in Saint Augustine

4.99 out of 5 average rating, 396 reviews

Your Home Away From Home

Guest favourite

Townhouse in Beaches

4.84 out of 5 average rating, 142 reviews

Fncd Yrd / PetsOK / Walk2Beach / 3 Bdrm / 2 Bthrm

Guest favourite

Tiny home in Avondale

4.93 out of 5 average rating, 135 reviews

Pet friendly tiny home w/fenced in yard by park

Guest favourite

Home in St. Augustine

4.91 out of 5 average rating, 145 reviews

Cozy Clean Comfortable Beach Home

Home in St. Augustine

4.82 out of 5 average rating, 116 reviews

Oceanfront Cottage_pet friendly

Guest favourite

Home in Southwest Jacksonville

4.92 out of 5 average rating, 75 reviews

Private, Safe, Quiet, Pet Friendly

Guest favourite

Home in Jacksonville

5 out of 5 average rating, 6 reviews

> Relaxing Home Near Mayo & Jax Beach <

Guest favourite

Bungalow in St. Augustine

4.95 out of 5 average rating, 192 reviews

Ooo Laa Laaah Beach one block! Fenced yard.

Quick stats about holiday rentals that are pet-friendly in Middleburg

Total rentals
20 properties
Total number of reviews
510 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
Local attractions
Publix Super Market at Middleburg Crossing, Dalton's Sports Grill and Nicole's Cafe in the Country

Destinations to explore