Holiday Rentals in St. Augustine, FL

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St. Augustine, FL holiday rentals
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4032 Holiday rentals and Airbnb in St. Augustine, FL

Best family friendly St. Augustine, FL holiday rentals

Among the 4032 accommodations in St. Augustine, FL, here are the 4 best family friendly rentals

The Grand Augustine L Heated Pool L Walk To Dntn - St. Augustine, FL
No reviews

The Grand Augustine L Heated Pool L Walk To Dntn

house, St. Augustine
This luxury residence is located in downtown St. Augustine, directly opposite Francis Field, offering immediate access to local attractions and events on foot.
This five-bedroom, four-bathroom property accommodates fifteen guests with a private swimming pool, a games room, and a separate garage apartment, with an identical adjacent property available to host up to thirty people.
Family-friendly Cottage In St. Augustine - 10 Min Drive To Downtown And Beaches! - St. Augustine, FL
10 1 review

Family-friendly Cottage In St. Augustine - 10 Min Drive To Downtown And Beaches!

cottage, St. Augustine
This St. Augustine holiday home is situated within 3.2km of the Tolomato and San Sebastian Rivers and Fort Mose Historic State Park, and within 4.8km of the Old Florida Museum and San Marco Antique Mall.
Sleeping eight guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen, private patio, garden, free Wi-Fi, and parking; enjoy nearby historical landmarks and attractions.
139 M² House ∙ 3 Bedrooms ∙ 7 Guests - St. Augustine, FL
No reviews

139 M² House ∙ 3 Bedrooms ∙ 7 Guests

house, St. Augustine
This Davis Shores residence is a short 1.6-kilometre drive from State Park Beach and within walking distance of historic St. Augustine's downtown area, accessible across the Bridge of Lions.
This single-storey property spans 139 square metres, accommodating up to seven guests with three bedrooms and two bathrooms, and features a fenced garden with a fire pit, a swimming pool, and a jacuzzi, with parking for three to four vehicles.
Historic Murphy's House - St. Augustine, FL
10 92 reviews

Historic Murphy's House

apartment, St. Augustine
This Uptown St. Augustine holiday home is a short walk from the St. Augustine & St. Johns County Visitor Information Centre and St. George Street, and within 1 km of the Castillo de San Marcos National Monument and Flagler College.
This 149 square metre property boasts four bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, terrace, garden, parking, and smart TV.

Best St. Augustine, FL holiday rentals with a pool

Among the 4032 accommodations in St. Augustine, FL, here are the 4 best rentals with a pool

The August - 3br 2.5ba Open Concept 1.4 Mi To Town - St. Augustine, FL
No reviews

The August - 3br 2.5ba Open Concept 1.4 Mi To Town

house, St. Augustine
Holiday house rental. Your accommodation will be located in St. Augustine.
Facilities and services include a washing machine, free parking and a fridge. Take advantage of the air conditioning in this house!
St. Augustine Beach Condo - Walk To Beach - St. Augustine, FL
10 17 reviews

St. Augustine Beach Condo - Walk To Beach

apartment, St. Augustine
This 2nd-floor apartment offers excellent access to St. Augustine's attractions, situated a 500-metre walk from the beach and a short drive to the Amphitheatre and historic downtown.
This 2-bedroom, 2-bathroom flat sleeps 4 guests and includes a fully equipped kitchen, air conditioning, and a communal swimming pool, with beach essentials provided for your convenience.
Seaside At Anastasia 202 Condo - St. Augustine, FL
8.8 31 reviews

Seaside At Anastasia 202 Condo

apartment, St. Augustine Beach
Seaside At Anastasia 202 Condo offers a three-bedroom apartment, a short 0.6km walk from St Augustine Beach and 0.8km from Anastasia State Park Beach, with Fort Matanzas and the St Augustine Lighthouse & Maritime Museum within a 3km and 5km radius respectively.
This self-catering holiday home features a private pool, free Wi-Fi, free parking, a fully equipped kitchen, and air conditioning; sleeping up to six guests and suitable for adults aged 25 and over.
Charming Condo W/ Pool  500 Yards To Beach, Near Lighthouse & Downtown - St. Augustine, FL
9.0 45 reviews

Charming Condo W/ Pool 500 Yards To Beach, Near Lighthouse & Downtown

apartment, St. Augustine Beach
This St. Augustine Beach flat offers direct access to the beach and is within walking distance of the splash park at St. Johns County Ocean Pier, situated approximately 6.5 kilometres from St. Augustine Lighthouse & Maritime Museum and 6.5 kilometres from historic downtown St. Augustine.
This 88 square metre condominium provides accommodation for up to four guests with two bedrooms, two bathrooms, a modern kitchen, air conditioning, on-site parking, and a communal swimming pool, with a private washer and dryer for added convenience.

Frequently asked questions about holiday rentals in St. Augustine, FL

  • What should a first-time visitor not miss in Saint Augustine, FL?

    You can't visit St. Augustine without seeing the Castillo de San Marcos, the oldest masonry fort in the US, and walking along the historic cobblestone streets of the St. Augustine Historic District. You'll also want to explore the beautiful St. Augustine Lighthouse and Maritime Museum.
  • What are the best Airbnb and holiday rentals in St. Augustine, FL?

  • Which neighborhood in Saint Augustine, FL should you consider for a vacation rental?

    The Historic District is a popular choice for vacation rentals, but you might prefer the quieter atmosphere of the Anastasia Island neighbourhood, which is just across the bridge. It's a bit further from the main attractions but offers a more relaxed vibe and beautiful beaches.
  • What are the most popular Airbnbs in St. Augustine, FL?

  • What are the top family-friendly attractions in Saint Augustine, FL?

    The St. Augustine Pirate & Treasure Museum is a big hit with kids, and the Ripley's Believe It Or Not! museum is always a fun time. Don't forget about the St. Augustine Alligator Farm Zoological Park, where you can see alligators and other reptiles.
  • What are the best holiday rentals with a pool in St. Augustine, FL?

  • What events or festivals should visitors check out in and around Saint Augustine, FL?

    St. Augustine has a vibrant calendar of events throughout the year. The annual St. Augustine Film Festival in March is a popular event, and the St. Augustine Greek Festival in May showcases Greek culture and cuisine. The St. Augustine Pirate & Treasure Festival in June is a fun event for the whole family.
  • What are the best rentals for families and kids in St. Augustine, FL?

  • What are the best budget-friendly activities in Saint Augustine, FL?

    You can easily spend a day exploring the historic district, visiting the Castillo de San Marcos, and walking along the city walls without spending a lot of money. The St. Augustine Beach is free to access and a great way to relax and enjoy the sunshine.
  • What are the best rentals or Airbnbs with a jacuzzi in St. Augustine, FL?

    The best vacation rentals or Airbnb with a jacuzzi in St. Augustine, FL are Anastasia Grand # 1-between Downtown And The Beach, Anastasia Grand #4 -Between Town And The Beach and Villa Tizoc.

  • What are the best restaurants with local dishes in Saint Augustine, FL?

    For authentic local cuisine, try The Columbia Restaurant, a historic Spanish restaurant serving traditional dishes like paella and sangria. Another popular choice is The Floridian, which offers a modern take on Southern comfort food.
  • What are the best walking or cycling routes in Saint Augustine, FL?

    The St. Augustine Historic District is perfect for a leisurely stroll, and you can also walk along the scenic waterfront of the Matanzas River. For a more challenging ride, try the 10-mile loop on the Vilano Beach Causeway.
  • Are there pet-friendly attractions in Saint Augustine, FL?

    Yes, many restaurants and businesses in St. Augustine are pet-friendly. You can also enjoy a walk along the beach with your furry friend at St. Augustine Beach.
  • What are the benefits of choosing a vacation rental in Saint Augustine, FL?

    Vacation rentals offer more space and privacy than hotels, and they often come with amenities like kitchens and laundry facilities. You can also find rentals in various locations, from the heart of the historic district to the quiet beaches of Anastasia Island.
  • What are the top sports attractions and facilities in Saint Augustine, FL?

    St. Augustine has a variety of sports facilities, including golf courses, tennis courts, and a public swimming pool at the Francis Field Recreation Complex. You can also find a variety of watersports activities, like kayaking, paddleboarding, and fishing.

Popular destinations

Best St. Augustine, FL holiday rentals with a balcony

Retro 50s Apartment, Patio & Walk To Downtown - St. Augustine, FL
9.0 36 reviews

Retro 50s Apartment, Patio & Walk To Downtown

apartment, St. Augustine
This St. Augustine apartment is ideally located in the Downtown Historic District, within a 1.6km walk of the San Sebastian River, Flagler College, and St. George Street.
The one-bedroom flat sleeps four, offering a fully equipped kitchen, private patio, free Wi-Fi, parking, and in-unit laundry facilities, all within easy reach of the St. Augustine Distillery and ACCORD Civil Rights Museum.
The Gaudi House- Pool/minutes To Dntn And Beach - St. Augustine, FL
9.6 65 reviews

The Gaudi House- Pool/minutes To Dntn And Beach

apartment, St. Augustine
This Greater Fullerwood holiday home in St Augustine, Florida, is situated less than 1.6km from the Matanzas River and Ponce de Leon's Fountain of Youth Archaeological Park, with the Old Florida Museum and San Marco Antique Mall within a 10-minute drive.
This 175 square metre property boasts four bedrooms, three bathrooms, sleeps eight guests, and includes a private pool, fully equipped kitchen, in-unit laundry, and a balcony; enjoying convenient access to local attractions.
Newconstructionluxury|pool|4beds|downtown - St. Augustine, FL
No reviews

Newconstructionluxury|pool|4beds|downtown

house, St. Augustine
This luxury townhome is located in St. Augustine's historic district, offering walking access to St. George Street and waterfront attractions, with rare on-site parking including two driveway and two garage spaces.
This spacious property accommodates up to eight guests across three levels, featuring private balconies, a fully equipped chef's kitchen, and access to community amenities such as a resort-style pool and hot tub, with a private dock available for an additional fee from late spring 2026.
Orange Grove Home - Fully Renovated Minutes From Downtown - St. Augustine, FL
No reviews

Orange Grove Home - Fully Renovated Minutes From Downtown

apartment, St. Augustine
This two-bedroom flat in St. Augustine's Oyster Creek district is a short walk to West King Street, offering convenient access to dining and entertainment, and is also within easy reach of St. Augustine Beach and Anastasia State Park, approximately 8 kilometers away.
This renovated apartment accommodates up to four guests with a queen bed and two twin beds, features air conditioning, internet, and parking, and boasts a garden with fruit trees, making it an ideal base for exploring local attractions such as World Golf Village, 11 kilometers distant.

Best St. Augustine, FL holiday rentals with parking

2br Cozy Blue Cottage Walk Dt Close To Beach - St. Augustine, FL
9.8 206 reviews

2br Cozy Blue Cottage Walk Dt Close To Beach

apartment, St. Augustine
This St. Augustine holiday home is centrally located in the historic district, within walking distance (under 1.6km) of the Castillo de San Marcos National Monument and a short drive (10-15 minutes) from St. Augustine Beach.
The two-bedroom, two-bathroom property sleeps six guests and includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, garden, parking and excellent guest reviews.
Overlooking Uptown St. Augustine - St. Augustine, FL
9.8 440 reviews

Overlooking Uptown St. Augustine

apartment, St. Augustine
This two-bedroom apartment is situated in the Uptown district of St Augustine, a historic area within walking distance of the city's main attractions.
The 127 square metre property, housed in a vintage Queen Anne style Victorian house, boasts a spacious rooftop deck and a fully equipped kitchen, making it an ideal choice for families or groups of up to six people.
Olastay Cottage - St. Augustine, FL
9.9 106 reviews

Olastay Cottage

apartment, St. Augustine
This St. Augustine holiday home, ideally located for exploring the city's historical attractions, offers convenient access to local amenities; precise distances to specific landmarks require further clarification.
The two-bedroom, two-bathroom property features a fully equipped kitchen, laundry facilities, a jacuzzi, and outdoor deck with grill, comfortably accommodating four guests.
Heart Of Historic District: Pet-friendly Home! - St. Augustine, FL
8.8 5 reviews

Heart Of Historic District: Pet-friendly Home!

apartment, St. Augustine
This pet-friendly apartment in downtown St. Augustine is a 1.4km walk from the Spanish Quarter Museum and under 1.6km from the Castillo de San Marcos National Monument.
The 46-square-metre self-catering flat features one bedroom, one bathroom, sleeps seven, and includes a private balcony, free Wi-Fi, a dishwasher, and parking (extra charge).
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