Pet-friendly vacation rentals in Middleburg

4.95 out of 5 average rating, 140 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.

4.84 out of 5 average rating, 316 reviews

Cozy, Pet-friendly Private House near downtown

Cozy, pet-friendly house with full kitchen and laundry facilities 1.5 miles from the center of historic downtown St Augustine. 6 miles from beaches. Down to earth vibe. Fenced yard. Good quality mattresses on both beds (Tempurpedic in master and Sealy pillow-top in the other). Driveway parks up to two cars. Walking distance to several bakeries and restaurants and a convenience store. Large dog crate provided. Happy to provide local recommendations - we love it here and want you to love it, too!

Condo in St. Augustine Beach

4.85 out of 5 average rating, 247 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

4.89 out of 5 average rating, 357 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.

4.91 out of 5 average rating, 286 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.

4.93 out of 5 average rating, 122 reviews

Home in Beaches

Luxury Beach Getaway w/ Heated Pool & Game Room

Recently built gorgeous 5-bedroom beach house with heated pool and game room with pool table, foosball, dart, shuffleboard, and ping pong. Living rooms on each level. Great for families. Gourmet chef's kitchen with 5 burner gas stove. Cable TV with all movie channels provided. Includes a putting green, bocci court, outdoor dining under the covered patio and a smart TV. BIKES INCLUDED PET FRIENDLY: We warmly welcome four-legged CANINE friends. No cats, please. (They don't like the beach!)

5 out of 5 average rating, 197 reviews

Cottage in Lincolnville

Walk Historic Downtown! “Blue Heaven”

Stunningly renovated cottage combines modern amenities with vintage charm... * 2 master suites with queen beds * Quiet neighborhood walking distance to explore The Nation's Oldest City * Clawfoot tubs inside and out (along with showers, of course!) * Big screened-in porch with hanging daybed * Off-street paved parking * Fenced yard, Weber grill, gas fire pit * Fast Wi-Fi and Smart TV * 2 blocks to Fish Camp, Ice Plant and LaNuvelle * 10 minute walk to central downtown St Augustine

5 out of 5 average rating, 202 reviews

Guesthouse in Beaches

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.

Apartment in St. Augustine

4.98 out of 5 average rating, 204 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).

Vacation home in St. Augustine

4.98 out of 5 average rating, 122 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 distance to local restaurants. Keurig coffee machine. Free WIFI & Internet with streaming for the TV. 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 $75.00 we allow 2 dogs

4.97 out of 5 average rating, 113 reviews

Home in Lincolnville

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.