Holiday Rentals in Pensacola, FL

1346 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Pensacola, FL holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Pensacola, FL

Best family friendly Pensacola, FL holiday rentals

Among the 1346 accommodations in Pensacola, FL, here are the 4 best family friendly rentals

Luxury Townhome Near Downtown And Pensacola Beach - Pensacola, FL
9.4 19 reviews
Pensacola, FL
31/07 – 01/08
SG$635/nightfor 1 night

Luxury Townhome Near Downtown And Pensacola Beach

3 2
apartment , Ferry Pass
This three-bedroom, three-bathroom Ferry Pass property is situated in Northeast Pensacola, conveniently located within 1.6km of University Town Plaza and Grizzly Axes, and under 5km from West Florida Hospital and Pensacola State College.
This family-friendly holiday home offers a swimming pool, on-site playground, free Wi-Fi, and a fully equipped kitchen, comfortably accommodating up to six guests.
Decompression Zone: Unwind At Modern Downtown Home - Pensacola, FL
10 2 reviews
Pensacola, FL
18/07 – 24/07
SG$475/nightTotal: SG$2850 (6 )

Decompression Zone: Unwind At Modern Downtown Home

1 5
apartment , Pensacola
This three-bedroom, two-bathroom cottage is located in Pensacola's historic Westside Garden District, offering an authentic local experience with convenient access to downtown dining, shopping, and the waterfront, being 2.9 kilometres from the Bay Center and 15.6 kilometres from Pensacola Beach.
This family-friendly dwelling accommodates up to six guests and features a spacious open-plan living area, a modern kitchen with a dishwasher, air conditioning, Wi-Fi, and two covered porches, with on-site parking available for two cars.
Stylish Modern Retreat In Downtown + Pool - Pensacola, FL
10 218 reviews
Pensacola, FL
17/10 – 24/10
SG$255/nightTotal: SG$1785 (7 )

Stylish Modern Retreat In Downtown + Pool

1 5
house , Pensacola
This three-bedroom townhouse is conveniently located near Pensacola, within a short drive of Pensacola Beach, Perdido Beach and Johnson's Beach. It has consistently received excellent ratings for location, cleanliness and user experience.
The property offers a comfortable and spacious layout that can accommodate up to seven guests. Enjoy access to a well-equipped kitchen, a private screened-in patio, a community pool, and smart TVs in each bedroom.
Shore Feels Like Home - Centrally Located - Pensacola, FL
9.7 35 reviews
Pensacola, FL
02/07 – 06/07
SG$1358/nightTotal: SG$5432 (4 )

Shore Feels Like Home - Centrally Located

1 10
apartment , Pensacola
This Pensacola property, ideal for families or groups, is situated near Baptist Hospital and Pensacola Mall (3 minutes' drive), Pensacola International Airport (7 minutes), and Pensacola Beach (15 minutes), offering easy access to key attractions.
Sleeping up to 10 guests in 4 bedrooms and 2 bathrooms, this newly renovated house boasts a fully equipped kitchen, garden, parking, and a converted garage entertainment area with laundry facilities; a blow-up mattress is available for extra guests.

Best Pensacola, FL holiday rentals with a pool

Among the 1346 accommodations in Pensacola, FL, here are the 4 best rentals with a pool

Central And Stylish With A Pool! - Pensacola, FL
10 3 reviews
Pensacola, FL
28/08 – 28/11
SG$131/nightTotal: SG$12052 (92 )

Central And Stylish With A Pool!

1 1
apartment , Ferry Pass
This three-bedroom, two-bathroom apartment in Ferry Pass, Pensacola, offers convenient proximity to West Florida Hospital (8km), Sacred Heart Hospital (14km), and Baptist Hospital (18km), as well as being 19km from Pensacola Beach.
The 6-guest property features a kitchen, air conditioning, parking, internet access, a community pool, and is modernly updated; enjoy easy access to downtown Pensacola (19km) and its attractions.
143 M² House ∙ 3 Bedrooms ∙ 8 Guests - Pensacola, FL
10 2 reviews
Pensacola, FL
25/07 – 28/07
SG$459/nightTotal: SG$1377 (3 )

143 M² House ∙ 3 Bedrooms ∙ 8 Guests

3 5
house , Pensacola
This Pensacola townhome, located one mile west of Pensacola's Historic District, is a 1.6km drive from Pensacola Beach and 1.6km from the Blue Wahoos Stadium.
The 142 square metre property boasts three bedrooms, two bathrooms, sleeps eight guests plus two small dogs, and includes a fully equipped kitchen, swimming pool, spa, and fitness centre.
The Lake House | 2 Bed, 2 Bath - Pensacola, FL
10 3 reviews
Pensacola, FL
01/09 – 30/09
SG$236/nightTotal: SG$6844 (29 )

The Lake House | 2 Bed, 2 Bath

2 2
apartment , Brent
This Pensacola, Florida lakefront property is conveniently located near University Town Plaza and Barnes Shopping Centre, a short 32km drive from Pensacola Beach.
This two-bedroom, two-bathroom house offers 74 square metres of living space, boasting a swimming pool, air conditioning, and high-quality furnishings, comfortably accommodating four guests and providing access to a shared pool and lakefront activities.
Chadwick Gardens Of Pensacola - Pensacola, FL
9.6 136 reviews
Pensacola, FL
17/09 – 21/09
SG$497/nightTotal: SG$1988 (4 )

Chadwick Gardens Of Pensacola

1 8
apartment , Pensacola
This four-bedroom apartment is located just 20 kilometres from the popular Pensacola Beach, situated in a quiet neighbourhood. It has received excellent ratings for cleanliness, location, and user experience.
The apartment can accommodate up to eight guests and features a spacious backyard oasis with a private pool, fire pit, hammocks, sun chairs, giant Jenga, and a 22-foot outdoor kitchen. Enjoy family-friendly fun with billiards and a future chip and putt area, perfect for a relaxing getaway.

Frequently asked questions about holiday rentals in Pensacola, FL

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

    You definitely shouldn't miss the National Naval Aviation Museum, it's a must-see for anyone interested in aviation history. Also, take a walk along the Pensacola Beach boardwalk for stunning views of the Gulf of Mexico.
  • What are the best Airbnb and vacation rentals in Pensacola, 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, FL among travelers.

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

    The historic district, known as Seville Square, is a great option for a vacation rental. It's full of charming Victorian houses and is close to lots of restaurants and shops.
  • What are the most popular Airbnbs in Pensacola, FL?

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

    The Pensacola Beach Gulf Breeze Zoo is a popular choice, and the National Museum of Naval Aviation also has a great kids' area. For a fun day out, check out the Gulf Breeze Water Park, it has slides and pools for all ages.
  • What are the best vacation rentals with a pool in Pensacola, FL?

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

    The peak season is during the summer months, so if you're looking for the best deals, book your rental in the spring or autumn. You'll still have great weather and fewer crowds.
  • What are the best rentals for families and kids in Pensacola, FL?

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

    A walk along the Pensacola Beach boardwalk is free and offers stunning views. You can also visit the historic Fort Barrancas, which is part of the Gulf Islands National Seashore and has free entry.
  • What are the best rentals or Airbnbs with a jacuzzi in Pensacola, FL?

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

    For fresh seafood, try The Fish House, it's a local favourite. If you're after something more casual, Peg Leg Pete's on Pensacola Beach serves up delicious seafood platters.
  • What are the best walking or cycling routes in Pensacola, FL?

    The Bay Bluffs Trail is a beautiful 10km paved trail that follows the Pensacola Bay. For a more challenging ride, try the 30km loop around the Naval Air Station.
  • Are there pet-friendly attractions in Pensacola, FL?

    Yes, many beaches in Pensacola allow dogs, including Casino Beach and Gulf Breeze. The Gulf Islands National Seashore also welcomes pets on its trails.
  • What are the benefits of choosing a vacation rental in Pensacola, FL?

    Vacation rentals offer more space and privacy compared to hotels. They often come with kitchens, so you can save money by cooking some of your meals. They also offer a more home-like experience.
  • What are the top sports attractions and facilities in Pensacola, FL?

    The Pensacola Blue Wahoos, a minor league baseball team, play at Blue Wahoos Stadium. The Pensacola Ice Flyers, a minor league hockey team, play at the Pensacola Bay Center.

Destinations nearby

Best Pensacola, FL holiday rentals with a balcony

Sea's The Day Getaway - Pensacola, FL
10 1 review
Pensacola, FL
09/07 – 12/07
SG$469/nightTotal: SG$1407 (3 )

Sea's The Day Getaway

1 7
house , Brent
Sea's the Day Getaway in Brent is located 5.1 kilometres from Fairfield Village Shopping Centre and 5 kilometres from Pensacola Regional Airport.
This air-conditioned holiday home offers 155 square metres of space with 1 bedroom, 2 bathrooms, and accommodation for up to 15 guests, featuring a fully equipped kitchen, complimentary WiFi, private parking, and a terrace with garden views.
Home W/ Patio & Games Near Dtwn Pensacola! - Pensacola, FL
9.8 6 reviews
Pensacola, FL
01/10 – 05/10
SG$329/nightTotal: SG$1316 (4 )

Home W/ Patio & Games Near Dtwn Pensacola!

3 4
house , Pensacola
This Pensacola holiday home is conveniently located near the city centre, approximately 2.4 kilometres from Bayview Dog Beach and 3.5 kilometres from Fairfield Village Shopping Centre.
The 214-square-metre property boasts three bedrooms, two bathrooms, and sleeps up to 15 guests, offering a fully equipped kitchen, air conditioning, private parking (at extra charge), and a garden.
Downtown Sea Escape Iv - Pensacola, FL
Pensacola, FL
26/12 – 28/02
SG$304/nightTotal: SG$19456 (64 )

Downtown Sea Escape Iv

3 2
apartment , Pensacola
The Downtown Sea Escape IV, a flat in Pensacola, is located in the city centre, offering convenient access to the Pensacola Historical Museum (2 kilometres), Saenger Theatre, and TT Wentworth Jr. Florida State Museum.
This 146 square metre apartment sleeps 14 guests, featuring three bedrooms, four bathrooms, air conditioning, a balcony, and a kitchen with a dishwasher and microwave, plus private parking.
90 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Pensacola, FL
10 1 review
Pensacola, FL
01/08 – 07/08
SG$206/nightTotal: SG$1236 (6 )

90 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

2 4
cottage , Pensacola
This detached house is located in Pensacola, offering a quiet escape with straightforward access to local sights.
This 90 square meter property accommodates up to four guests across two bedrooms and one bathroom, featuring a kitchen with a fridge, freezer, and microwave, as well as air conditioning, garden, terrace, and parking.

Best Pensacola, FL holiday rentals with parking

Lovely Townhome In Pensacola - Cozy & Modern Retreat - Pensacola, FL
9.2 61 reviews
Pensacola, FL
10/07 – 12/07
SG$521/nightTotal: SG$1042 (2 )

Lovely Townhome In Pensacola - Cozy & Modern Retreat

3 6
house , Ensley
This three-bedroom, two-bathroom Ensley townhome is conveniently located near Big Eagle railway station (5.6 km), Roger Scott Athletic Complex (9.8 km), and Fairfield Village Shopping Centre (12 km).
The 19-square-metre property offers free Wi-Fi, private parking, a terrace, and sleeps up to 11 guests, boasting a fully equipped kitchen and all linen provided.
The Downtown Two-door Historic Cottage - Pensacola, FL
10 13 reviews
Pensacola, FL
27/06 – 04/07
SG$402/nightTotal: SG$2814 (7 )

The Downtown Two-door Historic Cottage

1 2
apartment , Pensacola
This Pensacola Historic District cottage, a circa 1817 two-door bungalow, is within walking distance of Pensacola's downtown attractions, festivals, and waterfront parks, and a short drive (approximately 16km) from Pensacola Beach.
The 2-bedroom, 2-bathroom house sleeps up to six guests (with a linen fee for the sofa bed) and features a fully equipped kitchen, a backyard deck with a propane grill, and air conditioning; it's a smoke-free property with parking.
Chic 1br Loft | Downtown Location - Pensacola, FL
9.2 5 reviews
Pensacola, FL
01/07 – 30/09
SG$192/nightTotal: SG$17472 (91 )

Chic 1br Loft | Downtown Location

1 1
apartment , Pensacola
This Pensacola East Hill apartment, conveniently located a short drive from Pensacola Beach and downtown Pensacola, offers easy access to the Pensacola Bay Center (4 minutes), Blue Wahoos Stadium (6 minutes), and Gulf Breeze (7 minutes).
The 450 square metre (4844 square feet) self-catering property features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, gated backyard with outdoor dining and a fire pit, plus free parking and Wi-Fi.
Cheerful 3br Close To Downtown + Double Balcony - Pensacola, FL
9.4 5 reviews
Pensacola, FL
17/10 – 24/10
SG$257/nightTotal: SG$1799 (7 )

Cheerful 3br Close To Downtown + Double Balcony

3 5
house , Pensacola
This Pensacola holiday home is situated 1.6km from the Saenger Theatre and within a short drive of the TT Wentworth Jr. Florida State Museum and Pensacola Historical Museum.
The 145 square metre property boasts three bedrooms, three bathrooms, sleeping up to eleven guests, and features a fully equipped kitchen, free Wi-Fi, and two balconies; free private parking is also available.
©2026 cozycozy.com