Villas and Holiday homes in Pensacola, FL

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Pensacola, FL villas
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534 Villa rentals in Pensacola, FL

Best Pensacola, FL villas and holiday homes with a pool

Among the 534 accommodations in Pensacola, FL, here are the 4 best villas and holiday homes with a pool

Enjoy Sunsets At Fully Equipped 2br Condo On Beach - Pensacola, FL
9.4 8 reviews
Pensacola, FL
09/08 – 16/08
SG$417/nighttotal: SG$2919 (7 )

Enjoy Sunsets At Fully Equipped 2br Condo On Beach

2 4
house , Oriole Beach
This Oriole Beach holiday home boasts a beachfront location, 5.3km from Pensacola Beach Gulf Pier and 16-18km from various Pensacola attractions.
The 130 square metre property offers two bedrooms, two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, private pool, garden, parking, and Wi-Fi.
Very Private 3 Bed Home With Heated Pool Palms And Big Fenced Yard - Pensacola, FL
9.8 89 reviews
Pensacola, FL
09/08 – 16/08
SG$476/nighttotal: SG$3332 (7 )

Very Private 3 Bed Home With Heated Pool Palms And Big Fenced Yard

3 4
house , Myrtle Grove
This three-bedroom house in Pensacola, Florida, is situated in Myrtle Grove, approximately 10 kilometres from Fairfield Village Shopping Centre and 12 kilometres from the Saenger Theatre.
This 186 square metre property boasts a private pool, fully equipped kitchen, free Wi-Fi, and parking, sleeping up to six guests and offering easy access to local attractions.
The Pearl - Pensacola, FL
9.5 12 reviews
Pensacola, FL
09/08 – 16/08
SG$245/nighttotal: SG$1715 (7 )

The Pearl

3 4
house , Ensley
This Ensley holiday home, located in Pensacola, is 4.7km from Big Eagle Railroad Station and 13.2km from Fairfield Village Shopping Centre.
The 107-square-metre property boasts three bedrooms, two bathrooms, a private pool, free Wi-Fi, and parking, sleeping up to six guests and offering easy access to nearby water sports.
Sea-bound Str - Pensacola, FL
10 4 reviews
Pensacola, FL
16/10 – 23/10
SG$258/nighttotal: SG$1806 (7 )

Sea-bound Str

3 2
house , Pensacola
This holiday home in Pensacola is a 19-minute walk from the Saenger Theatre and 1.9 kilometres from the TT Wentworth Jr. Florida State Museum, Historic Pensacola Village, and Pensacola Historical Museum.
This air-conditioned cottage offers 147 square metres of living space with 3 bedrooms, 2 bathrooms, a fully equipped kitchen, a balcony, a sun terrace, an outdoor swimming pool, complimentary Wi-Fi, and free private parking for up to 13 guests.

Best Pensacola, FL villas and holiday homes with a kitchen

Safe And Quiet (900 Sq Ft) Guesthouse - Pensacola, FL
10 59 reviews
Pensacola, FL
27/06 – 29/06
SG$205/nighttotal: SG$410 (2 )

Safe And Quiet (900 Sq Ft) Guesthouse

1 2
house , Pensacola
This Pensacola guesthouse, situated in the Cordova Park neighbourhood, offers convenient access to Pensacola Beach, Pensacola International Airport, and downtown Pensacola, all within a reasonable driving distance.
The 900 sq ft (approximately 84 sq m) self-contained apartment boasts an open-plan layout, sleeping up to two guests, and includes a fully equipped kitchen (though with limited cooking utensils), a large-screen TV with cable, a pool table, and a private patio.
Waterfront Retreat W/ Outdoor Oasis In Pensacola - Pensacola, FL
Pensacola, FL
01/07 – 07/07
SG$1660/nighttotal: SG$9960 (6 )

Waterfront Retreat W/ Outdoor Oasis In Pensacola

1 2
cottage , West Pensacola
This West Pensacola holiday home is conveniently located within 5km of the Pensacola Outlet Mall, Warrington Village, and the Pensacola Big Game Fishing Club, and within 10km of Pensacola Naval Air Station and Baptist Health Care.
The self-catering property boasts 4.5 bathrooms, a private patio, a video game room, free on-site parking, and free Wi-Fi in communal areas, alongside a fully equipped kitchen including a microwave and dishwasher.
Adorable East Hill Florida Cottage Full Of Charm - Pensacola, FL
9.4 121 reviews
Pensacola, FL
02/09 – 11/09
SG$225/nighttotal: SG$2025 (9 )

Adorable East Hill Florida Cottage Full Of Charm

1 2
apartment , Pensacola
This charming cottage is located in a cool neighbourhood in Pensacola, just 5 minutes from the historic downtown and 15 minutes from the beach. The property has received excellent ratings for its location, cleanliness, and overall experience.
This three-bedroom house can comfortably accommodate up to six guests. It features a fully equipped kitchen, a spacious living area, a private garden, and a convenient car port. You can also enjoy the nearby Bayview Park, which offers a playground, tennis courts, a boat launch, and a dog park.
2 For 1️2 Separate Houses - Pensacola, FL
10 2 reviews
Pensacola, FL
28/08 – 28/11
SG$583/nighttotal: SG$53636 (92 )

2 For 1️2 Separate Houses

4 1
cottage , Warrington
This family-friendly cottage, offering 4 bedrooms and 2 bathrooms for up to 13 guests, is located in Warrington's downtown district, a 2-minute drive from Warrington Village Shopping Centre and a 15-minute walk to Blackwater River State Recreation Area.
This property provides a fully equipped kitchen with a fridge and microwave, air conditioning, a garden, and on-site parking, with complimentary Wi-Fi available for guests.

Frequently asked questions about villa rentals in Pensacola, FL

  • What are the must-see attractions in Pensacola, FL?

    You have to visit the Pensacola Naval Air Station Museum, it's a real gem! There's also the National Museum of Naval Aviation, which houses a collection of historic aircraft, and of course, the beautiful Pensacola Beach, with its white sand and clear waters.
  • What are the best villa rentals in Pensacola, FL?

    Among the villa rentals in Pensacola, FL, Sans Souci Unit 705, Cottage Under The Trees and Pensacola Oasis - Private - Safe - Central Location are the most popular ones.

  • What indoor activities for families are available in Pensacola, FL on rainy days?

    On a rainy day, head to the Pensacola Children's Museum or the Gulf Breeze Zoo. The Pensacola Museum of Art is also a great option for families, and they have a variety of exhibits that are perfect for all ages.
  • What are the best villa rentals with a pool in Pensacola, FL?

  • What are the best activities in Pensacola, FL?

    Pensacola is a real treat for all sorts of interests! You can enjoy the beach, explore the historic downtown area, or take a boat tour to see the dolphins. There are also plenty of opportunities for fishing, kayaking, and paddleboarding.
  • What are the best villa rentals with a jacuzzi in Pensacola, FL?

  • What are the advantages of renting a house or a villa in Pensacola, FL

    Renting a villa gives you more space and privacy than a hotel, and it's often more affordable for larger groups. You'll have access to a kitchen, laundry facilities, and often a private pool, making it great for families or groups of friends.
  • What are the best villa rentals for families and kids in Pensacola, FL?

    The best villa rentals for families and kids in Pensacola, FL are Pensacola Pelican Retreat, Jan And Feb 225 Per Night and Townhome A W/hottub In Downtown - Mins To Beach.

  • What food festivals or culinary events take place in and around Pensacola, FL?

    Pensacola has a great food scene! The Pensacola Seafood Festival is a popular event, and the Pensacola Beach Food and Wine Festival is another favourite. If you're here in the spring, you might catch the Pensacola Greek Festival.
  • What are the best pet friendly villa rentals in Pensacola, FL?

  • What exclusive experiences are available when visiting Pensacola, FL?

    If you're looking for something special, you could try a private fishing charter, take a sunset cruise on a sailboat, or even go on a dolphin-watching tour. The area has some great options for those seeking unique experiences.
  • What are the best villa rentals with parking in Pensacola, FL?

    Sans Souci Unit 705, Cottage Under The Trees and Pensacola Oasis - Private - Safe - Central Location are the best villa rentals with parking in Pensacola, FL.

  • Which part of Pensacola, FL would be ideal for a villa rental?

    For a villa rental, I'd recommend the area around Pensacola Beach or Gulf Breeze. You'll be close to the beach, and there are plenty of restaurants and shops nearby. You can also find some great villas in the historic downtown area, which is a bit further from the beach but offers a different kind of experience.

Destinations nearby

Best Pensacola, FL villas and holiday homes with air conditioning

Downtown Duplex W/ Fire Pit: 1 Mi To Waterfront - Pensacola, FL
10 1 review
Pensacola, FL
17/07 – 20/07
SG$470/nighttotal: SG$1410 (3 )

Downtown Duplex W/ Fire Pit: 1 Mi To Waterfront

3 6
house , Pensacola
The Retreat on Wright, a Pensacola holiday home, is conveniently located 1.9km from Historic Pensacola Village, 3.5km from Wayside Park, and offers easy access to Pensacola Regional Airport (9.9km).
This three-bedroom, two-bathroom property boasts 200 square metres of floor space, sleeps up to 11 guests, and includes a fully equipped kitchen, Wi-Fi, air conditioning, private parking, and a garden.
Downtown Coastal Cottage 7 Miles From Beach - Pensacola, FL
9.5 76 reviews
Pensacola, FL
30/07 – 31/07
SG$212/nightfor 1 night

Downtown Coastal Cottage 7 Miles From Beach

1 2
house , Pensacola
This Pensacola cottage is situated three blocks from Pensacola Bay, 11km from Pensacola Beach, and within walking distance of downtown amenities.
The self-contained property sleeps two guests in one bedroom with one bathroom, features a fully equipped kitchen, private garden, and a whole-house backup generator; nearby attractions include Publix, Walgreens, and Dollar General.
Two Beach Lofts For One Price - Pensacola, FL
9.5 7 reviews
Pensacola, FL
25/06 – 28/06
SG$617/nighttotal: SG$1851 (3 )

Two Beach Lofts For One Price

1 2
house , Midway
This Gulf Breeze holiday home, situated 17.6km from both Wayside Park and the Pensacola Visitor Information Centre, and 14km from Pensacola Beach Gulf Pier, offers convenient access to Midway attractions.
This two-bedroom property boasts two combined beach lofts, sleeping up to nine guests, and features a fully equipped kitchen, air conditioning, free Wi-Fi, private parking, and a flat-screen TV.
Walkable + Luxe ~ 1br Guesthouse W/ Fire Pit+grill - Pensacola, FL
9.9 154 reviews
Pensacola, FL
12/07 – 17/07
SG$225/nighttotal: SG$1125 (5 )

Walkable + Luxe ~ 1br Guesthouse W/ Fire Pit+grill

1 2
house , Pensacola
The Hatton Guesthouse, a modern one-bedroom guesthouse, is located in Pensacola's historic district, adjacent to Alga Brewery and within easy walking distance of various restaurants.
This self-catering property offers a king-size bed, a queen-size sofa bed, a fully equipped kitchen, laundry facilities, a private backyard with a fire pit and BBQ, and dedicated parking plus additional street parking, accommodating up to four guests.

Best Pensacola, FL villas and holiday homes with jacuzzi

Portofino Island P2-905 - Pensacola, FL
10 5 reviews
Pensacola, FL
17/10 – 24/10
SG$646/nighttotal: SG$4522 (7 )

Portofino Island P2-905

2 5
house , Oriole Beach
This beachfront property in Portofino Island, Pensacola Beach, Florida, is situated 6.7km from the Pensacola Beach Gulf Pier and offers stunning sea views.
Sleeping up to 11 guests, this two-bedroom, three-bathroom holiday home boasts a private swimming pool, jacuzzi, sauna, and fitness centre, alongside a fully equipped kitchen and access to a terrace, water park, and children's playground.
Portofino Island Resort 4-1305 - Pensacola, FL
8.8 4 reviews
Pensacola, FL
09/08 – 16/08
SG$603/nighttotal: SG$4221 (7 )

Portofino Island Resort 4-1305

2 4
house , Oriole Beach
Portofino Island Resort 4-1305, situated in Pensacola Beach, Florida, offers a self-catering holiday home a 6-minute walk from Pensacola Beach and 6.8km from Pensacola Beach Gulf Pier.
This 124 square metre property boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a private balcony with sea views, a fully equipped kitchen, swimming pool, sauna, and free Wi-Fi.
Portofino Island Resort 2-1306 - Pensacola, FL
8.0 1 review
Pensacola, FL
09/08 – 16/08
SG$538/nighttotal: SG$3766 (7 )

Portofino Island Resort 2-1306

2 4
house , Oriole Beach
This Portofino Island Resort 2-1306 villa in Oriole Beach is located a 6-minute walk from Pensacola Beach and 6.4 kilometres from the Pensacola Beach Gulf Pier.
This 124 square metre holiday home accommodates up to 11 guests in 2 bedrooms, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, a balcony with sea views, tennis court, parking, and free WiFi.
Pensacola Beach Penthouse W/ View + Pool Access! - Pensacola, FL
9.8 138 reviews
Pensacola, FL
17/10 – 24/10
SG$398/nighttotal: SG$2786 (7 )

Pensacola Beach Penthouse W/ View + Pool Access!

2 5
house , Oriole Beach
This Oriole Beach penthouse apartment boasts stunning views and is a six-minute walk from Pensacola Beach, 6.7 km from the Pensacola Beach Gulf Pier, and 17.7 km from Wayside Park and the Pensacola Visitor Information Centre.
The 124 square metre property features three bathrooms, two bedrooms, a fully equipped kitchen, private terrace, and access to a swimming pool, jacuzzi, spa, fitness centre and tennis court; sleeping up to four guests comfortably.
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