Holiday Rentals in Pensacola Beach, FL

5681 available vacation rental offers

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Pensacola Beach, FL holiday rentals
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Best Holiday rentals and Airbnb offers in Pensacola Beach, FL

Best family friendly Pensacola Beach, FL holiday rentals

Among the 5681 accommodations in Pensacola Beach, FL, here are the 4 best family friendly rentals

Gulf Views-  Luxurious Amenities- Sleeps 4 Adults 2 Kids! - Pensacola Beach, FL
9.6 117 reviews
Pensacola Beach, FL
01/09 – 04/09
SG$506/nighttotal: SG$1518 (3 )

Gulf Views- Luxurious Amenities- Sleeps 4 Adults 2 Kids!

1 3
apartment , Gulf Breeze
This apartment is located in Pensacola Beach, just 1.5km from Pensacola Beach Beaches and Pensacola Beach Pier, offering easy access to the area's beautiful coastline and attractions. It has received excellent user ratings, making it a popular choice for travellers.
The apartment has one bedroom and one bathroom, accommodating up to six guests. You can enjoy a range of amenities including a private pool, fitness centre, sauna and spa, as well as an indoor and outdoor pool, perfect for relaxing and enjoying the Florida sunshine.
The Pensacola Beach Resort - Pensacola Beach, FL
9.5 4078 reviews
Pensacola Beach, FL
05/10 – 09/10
SG$317/nighttotal: SG$1268 (4 )

The Pensacola Beach Resort

1 2
resort , Gulf Breeze
The Pensacola Beach Resort is located directly on Pensacola Beach, just a short walk from the Pensacola Beach Gulf Pier and a short drive from the Naval Live Oaks Nature Preserve. The resort has received very good user ratings and excellent ratings for location and cleanliness.
The resort offers a range of rooms, including those with ocean or bay views. It features a restaurant, bar, fitness centre, swimming pool, and a kids' club, as well as activities like bicycle rentals, paddleboard lessons, and margarita-making classes.
Ocean Tranquility Label By Guest“heaven On Earth”. - Pensacola Beach, FL
9.9 119 reviews
Pensacola Beach, FL
08/08 – 09/08
SG$931/nightfor 1 night

Ocean Tranquility Label By Guest“heaven On Earth”.

1 6
apartment , Gulf Breeze
This Gulf Breeze condo boasts an oceanfront location with direct beach access, offering stunning views of the Gulf of Mexico and proximity to local attractions.
The two-bedroom, two-bathroom apartment sleeps six guests comfortably, featuring a king-size bed, queen, twin bunk beds, a queen-size sofa bed, a fully equipped kitchen, in-unit laundry, and private garage parking within a gated community, plus access to a swimming pool and Jacuzzi.
20th Floor Sunrise Views Portofino Tower 2 Amenities Included  Sleeps 6 - Pensacola Beach, FL
10 252 reviews
Pensacola Beach, FL
03/07 – 10/07
SG$766/nighttotal: SG$5362 (7 )

20th Floor Sunrise Views Portofino Tower 2 Amenities Included Sleeps 6

2 4
apartment , Oriole Beach
This Oriole Beach apartment, a short 0.8km walk from Santa Rosa Sound and Pensacola Beach, offers convenient access to Opal Beach and Park East On-Leash Dog Beach within a 2.4km radius.
The 124 square metre property features two bedrooms, three bathrooms, and sleeps six, boasting a private balcony, full kitchen, and access to a swimming pool, jacuzzi, fitness centre, sauna, and tennis court.

Best Pensacola Beach, FL holiday rentals with a pool

Among the 5681 accommodations in Pensacola Beach, FL, here are the 4 best rentals with a pool

Gorgeous Views Of The Gulf From The Balcony! - Pensacola Beach, FL
9.4 76 reviews
Pensacola Beach, FL
06/08 – 10/08
SG$669/nighttotal: SG$2676 (4 )

Gorgeous Views Of The Gulf From The Balcony!

2 8
apartment , Gulf Breeze
This apartment is located in Villa Sabine, a neighbourhood in Pensacola Beach, just a short distance from the beach, entertainment, shopping, and dining. It has received excellent reviews from previous guests.
The apartment is a two-bedroom, two-bathroom property with a floor area of 100 square metres and can accommodate up to eight guests. The apartment offers a range of amenities including a swimming pool, tennis court, fitness centre, fire pit, charcoal grills, a private balcony, a fully equipped kitchen, and free high-speed internet and Wi-Fi.
Beautiful Views Of The Intracoastal Waterway In This 3 Bd, 2.5 Bth Condo! - Pensacola Beach, FL
9.4 19 reviews
Pensacola Beach, FL
16/07 – 19/07
SG$768/nighttotal: SG$2304 (3 )

Beautiful Views Of The Intracoastal Waterway In This 3 Bd, 2.5 Bth Condo!

3 6
apartment , Navarre Beach
This Navarre Beach condo, a short walk (under 1.6km) from Santa Rosa Sound and Navarre Beach, offers easy access to Opal Beach and Gulf Islands National Seashore (within a 24km radius).
Sleeping six guests, this three-bedroom, three-bathroom apartment boasts a fully equipped kitchen, free Wi-Fi, a terrace, swimming pool, tennis court, parking, and barbecue facilities; enjoy nearby watersports and beach activities.
Boardwalk F3-chic Bayside 2br, Easy Beach Access, Pool - Pensacola Beach, FL
9.5 80 reviews
Pensacola Beach, FL
31/08 – 02/09
SG$430/nighttotal: SG$860 (2 )

Boardwalk F3-chic Bayside 2br, Easy Beach Access, Pool

2 4
apartment , Gulf Breeze
This two-bedroom apartment is located at the Boardwalk in Gulf Breeze, just a short walk from the beach and close to a variety of restaurants and shops. It has received excellent ratings for its cleanliness, location, and overall experience.
The apartment spans 119 square metres and comfortably accommodates up to 8 guests, with a king bed, two queen beds, and a queen sleeper sofa. It features a shared outdoor pool, picnic tables, and a boat/Jet Ski launch, making it ideal for families or groups seeking a relaxing and enjoyable stay.
Wake Up To Emerald Gulf Views - Pensacola Beach, FL
9.9 69 reviews
Pensacola Beach, FL
05/07 – 08/07
SG$1661/nighttotal: SG$4983 (3 )

Wake Up To Emerald Gulf Views

5 13
apartment , Oriole Beach
This Pensacola Beach holiday home enjoys an unparalleled beachfront location in the exclusive Oriole Beach gated community, offering direct access to both the Gulf and Sound beaches and is minutes from the Pensacola Beach boardwalk and shops.
Sleeping up to 16 guests, this five-bedroom, five-bathroom property boasts a chef's kitchen, game room with arcade and Xbox 360, rooftop deck, private dock with fish cleaning station, elevator access, and abundant beach equipment including chairs, umbrellas, and a wagon.

Frequently asked questions about holiday rentals in Pensacola Beach, FL

  • What should a first-time visitor not miss in Pensacola Beach, FL?

    You absolutely must visit the Pensacola Beach Gulf Pier, it's a local favourite. It's a great spot to watch the sunset, go fishing, or just enjoy the views of the Gulf of Mexico. Another must-do is to take a walk or cycle along the beach, it's a beautiful way to take in the scenery. And if you're looking for some history, be sure to check out Fort Pickens, a historic fort that played a key role in the defence of the area.
  • What are the best Airbnb and vacation rentals in Pensacola Beach, FL?

    Portofino Tower 3 Unit 1601, Sans Souci Unit 705 and Spectacular Beach Front Views Free Lazy Days Beach Chairs & Umbrella Included are the most popular Airbnb and vacation rentals in Pensacola Beach, FL among travelers.

  • Which neighborhood in Pensacola Beach, FL should you consider for a vacation rental?

    For a beachside vacation, you can't go wrong with the neighbourhoods of Santa Rosa Island or Perdido Key. They both offer a range of vacation rentals, from beachfront condos to charming cottages. Santa Rosa Island is home to the main part of Pensacola Beach, while Perdido Key is a bit quieter and more secluded. Both offer great access to the beach and other attractions.
  • What are the most popular Airbnbs in Pensacola Beach, FL?

  • What are the top family-friendly attractions in Pensacola Beach, FL?

    Pensacola Beach is a great place for families. The Gulf Breeze Zoo is a great place to spend a few hours, and the National Naval Aviation Museum is a great place to learn about the history of aviation. If the kids need to burn off some energy, the Pensacola Beach Boardwalk is a great place to run around, and the Pensacola Beach Gulf Pier is a great place to go fishing.
  • What are the best vacation rentals with a pool in Pensacola Beach, FL?

  • When is the best time to book a vacation rental in Pensacola Beach, FL?

    The best time to book a vacation rental in Pensacola Beach is during the shoulder season, from April to May or September to October. The weather is still pleasant, but the crowds are smaller and the prices are lower. If you're looking for a quieter experience, you can also consider visiting during the winter months, from November to March. The weather is still mild, and you'll have the beach practically to yourself.
  • What are the best rentals for families and kids in Pensacola Beach, FL?

  • What events or festivals should visitors check out in and around Pensacola Beach, FL?

    The Pensacola Beach Air Show is a popular event that takes place every year in July, and the National Shrimp Festival is a fun and lively event that takes place every year in October. If you're looking for something a bit more low-key, the Pensacola Beach Wine and Food Festival is a great option.
  • What are the best rentals or Airbnbs with a jacuzzi in Pensacola Beach, FL?

    The best vacation rentals or Airbnb with a jacuzzi in Pensacola Beach, FL are Portofino Tower 3 Unit 1601, Sans Souci Unit 705 and Spectacular Beach Front Views Free Lazy Days Beach Chairs & Umbrella Included.

  • What are the best budget-friendly activities in Pensacola Beach, FL?

    There are plenty of free and budget-friendly things to do in Pensacola Beach. Take a walk or cycle along the beach, visit the Pensacola Beach Gulf Pier, or explore the Pensacola Beach Boardwalk. You can also pack a picnic and enjoy a meal on the beach.
  • What are the best restaurants with local dishes in Pensacola Beach, FL?

    For authentic local dishes, you can't beat the Peg Leg Pete's, a popular seafood restaurant that serves up fresh catches. The Grand Marlin is another great option, serving up a variety of seafood dishes with a modern twist. If you're looking for something a bit more casual, the Flounders Chowder House is a great choice, known for its delicious seafood chowder.
  • What are the best walking or cycling routes in Pensacola Beach, FL?

    The Pensacola Beach Boardwalk is a great place to go for a walk or cycle, and it offers stunning views of the Gulf of Mexico. For a more challenging ride, you can try the Pensacola Beach Bike Trail, which winds its way through the dunes and offers beautiful views of the beach.
  • Are there pet-friendly attractions in Pensacola Beach, FL?

    Yes, there are plenty of pet-friendly attractions in Pensacola Beach. Many of the beaches are dog-friendly, and there are a number of restaurants and shops that welcome furry friends. The Pensacola Beach Gulf Pier is also pet-friendly, so you can enjoy the views with your canine companion.
  • What are the benefits of choosing a vacation rental in Pensacola Beach, FL?

    Vacation rentals offer a number of benefits over hotels, including more space, privacy, and the ability to cook your own meals. They are also often more affordable, especially if you are travelling with a large group.
  • What are the top sports attractions and facilities in Pensacola Beach, FL?

    Pensacola Beach offers a variety of sports activities, including swimming, fishing, boating, and kayaking. The Pensacola Beach Gulf Pier is a popular spot for fishing, and there are a number of boat rentals available. For those who prefer to stay on land, there are a number of tennis courts and golf courses in the area.

Destinations nearby

Best Pensacola Beach, FL holiday rentals with a balcony

248 M² House ∙ 4 Bedrooms ∙ 12 Guests - Pensacola Beach, FL
Pensacola Beach, FL
20/07 – 23/07
SG$1096/nighttotal: SG$3288 (3 )

248 M² House ∙ 4 Bedrooms ∙ 12 Guests

4 2
house , Oriole Beach
Juela on the Beach, a Pensacola Beach rental property offering direct Gulf front access, is situated on the Gulf Coast, providing easy beach access.
This four-bedroom, four-bathroom house boasts 247 square metres of space, accommodating up to twelve guests and featuring a private swimming pool, jacuzzi, and a fully equipped kitchen with granite countertops; nearby Pensacola Beach offers restaurants and entertainment.
316 M² House ∙ 5 Bedrooms ∙ 18 Guests - Pensacola Beach, FL
10 1 review
Pensacola Beach, FL
10/09 – 13/09
SG$1001/nighttotal: SG$3003 (3 )

316 M² House ∙ 5 Bedrooms ∙ 18 Guests

5 10
house , Navarre Beach
This waterfront residence in Grand Navarre provides direct access to the Santa Rosa Sound and Intracoastal Waterway, situated only a few kilometres from the Gulf's pristine beaches.
This expansive 316 square metre villa offers five bedrooms, six bathrooms, and accommodates eighteen guests, featuring a private heated swimming pool, a dock with a boat lift, and complimentary kayaks and beach equipment.
Let's Do Sunset - Dock, Gulf Access, Sunset Deck + Pet Friendly - Pensacola Beach, FL
10 14 reviews
Pensacola Beach, FL
20/07 – 24/07
SG$1640/nighttotal: SG$6560 (4 )

Let's Do Sunset - Dock, Gulf Access, Sunset Deck + Pet Friendly

5 11
apartment , Gulf Breeze
This Pensacola Beach villa in Villa Primera boasts a direct sound-front location with a private pier, less than 0.8km from the Gulf beach and a short drive from Pensacola Beach's shops and restaurants.
This six-bedroom, five-bathroom property offers 279 square metres of space, sleeping up to 17 guests, and features a chef's kitchen, elevator, waterfront deck, spa, and a private pier for boating and fishing; a playground and basketball court are nearby.
Dog-friendly House Near The Beach, Balconies, Washer&dryer, & Cable - Pensacola Beach, FL
Pensacola Beach, FL
09/07 – 12/07
SG$2378/nighttotal: SG$7134 (3 )

Dog-friendly House Near The Beach, Balconies, Washer&dryer, & Cable

8 9
apartment , Navarre Beach
This Navarre Beach residence is located near the ocean, providing convenient access to Navarre Beach and Opal Beach, and is also close to Navarre Beach Marine Park.
This spacious 308 square meter holiday home accommodates up to 16 guests with 8 bedrooms and 6 bathrooms, featuring a fully equipped kitchen, air conditioning, a terrace, a balcony, and a garden.

Best Pensacola Beach, FL holiday rentals with parking

Breathtaking Full Ocean Views In The Heart Of Pensacola Beach Ei 10th Flr 2bd2ba - Pensacola Beach, FL
9.8 64 reviews
Pensacola Beach, FL
05/09 – 12/09
SG$432/nighttotal: SG$3024 (7 )

Breathtaking Full Ocean Views In The Heart Of Pensacola Beach Ei 10th Flr 2bd2ba

2 2
apartment , Gulf Breeze
This 10th-floor condominium is located directly on Pensacola Beach, a short walk from dining, shops, and nightlife, and close to the Pensacola Beach Boardwalk.
This two-bedroom, two-bathroom apartment sleeps four and offers direct beach access with gulf-front windows, a modern kitchen, a master suite with a private balcony, and on-site amenities including two swimming pools, a hot tub, a gym, and a sauna.
️Private Pool + Game Room | Sleeps 17 | Steps To Beach | Owb Beach House - Pensacola Beach, FL
Pensacola Beach, FL
28/08 – 31/08
SG$985/nighttotal: SG$2955 (3 )

️Private Pool + Game Room | Sleeps 17 | Steps To Beach | Owb Beach House

7 17
apartment , Oriole Beach
This Pensacola Beach residence is situated in the Toilla Segunda district, a mere 100 metres from Pensacola Beach and a short drive to Fort Pickens and the Gulf Islands National Seashore.
This spacious 206 square metre holiday home accommodates up to 17 guests across 7 bedrooms and 3 bathrooms, featuring a private swimming pool, expansive exterior decking, a game room with ping pong and darts, and complimentary bicycles for exploring the local area.
Huoneisto ∙ 2 Makuuhuonetta ∙ 7 Vierasta - Pensacola Beach, FL
Pensacola Beach, FL
27/06 – 30/06
SG$346/nighttotal: SG$1038 (3 )

Huoneisto ∙ 2 Makuuhuonetta ∙ 7 Vierasta

2 2
apartment , Gulf Breeze
This apartment is located on the Santa Rosa Sound in Pensacola Beach, a short drive or trolley ride from local dining and entertainment.
This family-friendly holiday flat sleeps seven guests across two bedrooms and two bathrooms, offering complimentary use of three kayaks, an on-site outdoor pool, a private fishing pier, and wheelchair-accessible facilities, with parking for two vehicles.
Bright And Sunny Gulf Front Townhome, Steps From The Water - Pensacola Beach, FL
9.6 119 reviews
Pensacola Beach, FL
03/07 – 07/07
SG$1574/nighttotal: SG$6296 (4 )

Bright And Sunny Gulf Front Townhome, Steps From The Water

4 4
apartment , Gulf Breeze
White Sands #473, a Gulf-front townhouse in Pensacola Beach, offers stunning sunrise and sunset views and is located minutes from local shops, restaurants, and the Museum of Commerce.
This 188 square metre (2024 square feet) property boasts a spacious four-bedroom, three-bathroom layout sleeping up to 14 guests, complete with a fully equipped kitchen, private balconies, Wi-Fi, and garage parking; nearby activities include jet skiing, scuba diving, hiking, and cave exploring.
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