Cottage vacation rentals in Anastasia Island

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Top-rated cottage rentals in Anastasia Island

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Guest favourite

Cottage in St. Augustine

4.99 out of 5 average rating, 104 reviews

Downtown Historic Carriage House with Parking

Welcome to Little Sister's House, a bright and delightful historic carriage house located only steps from all fabulous St. Augustine has to offer. Beautifully furnished and full of vintage touches, this darling cottage is three blocks from St. George Street & the Castillo de San Marcos. The beach is just a short drive away. This light, charming, private space is the perfect spot for a get away. Sip coffee on the porch, or go for a stroll to town. Locally operated by lifelong St. Augustinians.

Jul. 26 – Aug. 2

$310 CAD per night

Guest favourite

Cottage in St. Augustine

4.89 out of 5 average rating, 284 reviews

Unique mid-century modern Lemon Tree Cottage

This bright and cheery Mid-Century modern inspired cottage is located in the heart of St. Augustine FL. Tucked away on a quiet tree-lined street, only 2 miles away from the historic downtown and 2.5 miles away from Vilano Beach. This stylish and fun cottage will surely be a memorable experience. Great Value for a 2 bedroom single family home near downtown. Comfy furniture and queen mattresses. Offers a full kitchen, plenty of off street parking, backyard. Smart TV, Netflix, high-speed internet.

Oct. 20 – 27

$231 CAD per night

Guest favourite

Cottage in St. Augustine

4.98 out of 5 average rating, 179 reviews

Bamboo Lane Hideaway near AMP, Downtown & Beaches

Sophisticated, tropical hideaway. Your retreat… quiet, respectful & peaceful. All are welcome here with love and respect. Perfect for singles, couples, looking to rest and relax or to explore this historic Florida shore, the ‘Bamboo lane hideaway’ offers unique accommodations complete with a custom-designed interior, laid-back beach vibe, and complimentary parking pass for downtown. Explore the nearby Lighthouse, Zoo, white-sand Beaches, Amphitheater & Downtown all less than 1.6 miles away.

Oct. 12 – 19

$220 CAD per night

Guest favourite

Cottage in St. Augustine

4.94 out of 5 average rating, 128 reviews

Coastal Cottage -firepit, pet fence, kayaks, bikes

Located in the historic Lighthouse Park neighborhood, this charming 1940s coastal cottage is easy strolling distance to the Lighthouse, Alligator Farm, mini-golf, cafes & more! It is only a 0.8-mi walk to the Bridge of Lions, where you can walk over the Bay to downtown St. Augustine. You couldn't ask for a better location! It's on Anastasia Island so you're a short walk/bike/car ride from the beach & Ampitheater. It's cozy, pet & kid-friendly with a big backyard. Kayaks & bikes available!

Oct. 9 – 16

$320 CAD per night

Guest favourite

Cottage in St. Augustine

4.98 out of 5 average rating, 140 reviews

Perfect Waterfront Retreat w/Pool & Rooftop Deck

You've found your waterfront oasis tucked under the White Birds of Paradise! This spacious retreat was formerly a commercial art gallery. Two queen beds, one full bathroom & full kitchen make for comfortable living! You have a fenced path leading you down to the beautiful waters of Salt Run where a rooftop deck & salt water in-ground pool invites you to relax and slow down. Less than a mile to downtown St. Augustine, a little over a mile to the Amphitheater and about 3 miles to the beach.

Oct. 8 – 15

$379 CAD per night

Superhost

Cottage in St. Augustine

4.79 out of 5 average rating, 169 reviews

Mermaid Cove Vilano Beach/Queen. Sleeps 2. Pet fee

Bungalow/300 sq/Detached from duplex/Sleeps 2, queen/1 folding bed.Pet/fee.Fenced outdoor space/table/chairs. Full shower/fridge/kitchenette/sheets/towels. George Foreman grill/outdoor shower. 120 steps to beach/no roads to cross. Towels, chairs/umbrella/cooler. Coffee maker, microwave,induction oven. 3 miles to downtown/1 mile Pier/8 mile Guana Park Potential for noise: Directly on Historic A1A Highway. Across/BP gas station **See Family Memories for 10 for a gathering .

Mar. 3 – 10

$200 CAD per night

Superhost

Cottage in St. Augustine

4.91 out of 5 average rating, 107 reviews

The Shire on 1 acre marshfront with dock and Spa

One of a kind 1930s historic home, newly renovated and transformed into a beautiful secluded getaway. new luxury finishes, while holding its traditional charm. No Events allowed. Rooftop deck, sunrise views of the Atlantic ocean, Downtown, and sunsets over the river. The new dock with covered roof hosts a national geographic like eco system. It’s short walk to the beach and 3 miles to downtown St George street. Follow along @carcabaroad for weekly content of the home.

Jun. 3 – 10

$967 CAD per night

Guest favourite

Cottage in St. Augustine

4.91 out of 5 average rating, 224 reviews

Livin’ the Dream at St. Augustine Beach

Bright beachy unit with all amenities including community pool, close public beach access and essentials including bedding, towels, beach cruiser bikes and grill. Enclosed porch and outside deck are ideal for grilling out or hanging out. My home is located in Peppertree RV Resort . The public beach access is a short 10 minute walk away. The unit has parking for two vehicles with extra parking available in an overflow lot. A washer and dryer are located inside the unit.

Sep. 29 – Oct. 6

$160 CAD per night

Guest favourite

Cottage in St. Augustine

4.96 out of 5 average rating, 145 reviews

Magical courtyard private cottage by beach

Very comfortable, relaxed island breezy appeal. King and queen bedrooms, additional quality blow up queen mattress. Open living space with French doors leading to back deck. Spacious kitchen, dining & breakfast nook. Gorgeous private courtyard with string lights for magical night time ambiance. Expect everything you may need with complimentary wine and donuts upon arrival. Local dining scene is incredible! No smoking inside period! *See house rules for pet info.

Dec. 1 – 8

$298 CAD per night

Guest favourite

Cottage in St. Augustine

4.96 out of 5 average rating, 161 reviews

Masters Manor A Gothic Themed Cottage

This 1900 gothic style charmer is a unique place to call home while visiting our city. From the dark aesthetic, custom woodwork and warm lighting ..you'll find this home has a very comforting feel to it. The eclectic decor offers a whimsical, inviting atmosphere! It's located in West Augustine under 2 mi from downtown and less than 6 mi from both beaches. A local Brewery, Bakery and Breakfast joint are .5 away Photo shoots, cinematography/music videos welcomed🦇

Jul. 11 – 18

$220 CAD per night

Guest favourite

Cottage in St. Augustine

5.0 out of 5 average rating, 103 reviews

Large private yard, walk to town, bike to beach

Monarch Gardens is a cozy 1 bedroom/1 bathroom newly renovated cottage nestled on a 1/4 acre fence-lined private lot. Surrounded by trees, birds and butterflies, you are within walking and biking distance (2 bikes provided) to historic downtown (.5 miles) and the beach at Anastasia State Park (1.5 miles), as well are many restaurants, bars, shops and art galleries. The neighborhood is quiet and safe and the perfect retreat after a busy day of seeing the sights.

Aug. 28 – Sep. 4

$287 CAD per night

Superhost

Cottage in Saint Augustine

4.81 out of 5 average rating, 302 reviews

Sea La Vie Beach Studio

Our renovated studio is on a quiet cul-de-sac, one block from the beach! It is one side of a duplex and is perfectly located within walking distance to restaurants, family-friendly activities, nightlife, and public transport. It is across the street from the pier and the piers weekly farmers market. It is a short drive to historic downtown St Augustine. The neighborhood is quiet and safe. Our place is good for couples, solo adventurers and business travelers.

Oct. 10 – 17

$166 CAD per night