Pet-friendly holiday rentals in Lakeside

4.95 out of 5 average rating, 142 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, 320 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!

Apartment in St. Augustine Beach

4.85 out of 5 average rating, 249 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, 365 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, 290 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.

5 out of 5 average rating, 202 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, 205 reviews

Guest house 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.

4.87 out of 5 average rating, 105 reviews

Cozy Pet-Friendly Cottage

This cozy cottage is thoughtfully designed for a relaxing getaway. The fully stocked kitchen and coffee bar are perfect for home-cooked meals and morning brews, while the spacious, fenced backyard is great for pets to roam freely. Start your day on the covered patio or unwind in the evening with a quiet dinner. Located just minutes from historic downtown, the beach, shopping, and easy highway access, all in a peaceful neighborhood—your perfect home away from home awaits!

4.98 out of 5 average rating, 208 reviews

Flat in St. Augustine

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).

Holiday home in St. Augustine

4.98 out of 5 average rating, 124 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, 116 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.