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    Holiday Rentals with Pools in Pensacola

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      Travellers to Pensacola are booking April dates now. Secure your holiday rental today, and have the perfect trip.
      59 Matching Rentals in PensacolaView all 91 rentals
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      ROMANTIC Beach Getaway for Couple!1 / 45
      (21)Excellent
      1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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      Pet-friendly Apartment with pool, hot tub & boat ramp near Pensacola Beach1 / 26
      (1)Excellent
      1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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      $199/night Brand New Interior, many upgrades1 / 23
      (5)Excellent
      3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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      Old River 7C1 / 14
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Terrace
      • Parking
      • Cable/satellite TV
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      • Washer
      • Balcony
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      Pet friendly
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      Smoking allowed
      About this property
      Charming 2 BR on Old River in Perdido Key with assigned Boat Slip! This 3rd-floor condo has wonderful views of the Gulf of Mexico from the Front Balcony and Kitchen door. The Main Living area and Master Bedroom have the ever entertaining boating activity on Ole River! The Condo is Located only 1.5...
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      Pensacola, Florida Panhandle 32507
      Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Yosanmine 10ad1 / 10
      (22)Very good
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Private Outdoor Pool (Heated)
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Beachcomber Bliss 38c1 / 22
      (22)Very good
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Sea Esta 11bd1 / 16
      (20)Very good
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Parrot-dise 13au1 / 11
      (6)Very good
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Hot Tub
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Tropical Therapy 5cu1 / 11
      (20)Very good
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Private Outdoor Pool (Heated)
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Belize Place 4c1 / 16
      (17)Very good
      3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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      Rancho Deluxe 27cu1 / 16
      (18)Excellent
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Private Outdoor Pool (Heated)
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      Pet friendly
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Purple Parrot 18cu1 / 12
      (15)Very good
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Parking
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Lazy Daze 10au1 / 26
      (29)Very good
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Hot Tub
      • Private Outdoor Pool (Heated)
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      Pet friendly
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      Smoking allowed
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Ocean Melodies 10b1 / 17
      (2)Very good
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Private Outdoor Pool (Heated)
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      Pet friendly
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      Smoking allowed
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Sea La Vie 2cd1 / 10
      (14)Very good
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Private Outdoor Pool (Heated)
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      Pet friendly
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      Location Information
      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Perdido Sun Resort 9121 / 11
      (1)Excellent
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Parking
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      • Private Outdoor Pool (Heated)
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Andalucia 16c1 / 18
      (19)Very good
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Private Outdoor Pool (Heated)
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      • Hot Tub
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      Pet friendly
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      Smoking allowed
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Slow Mo 17ad1 / 12
      (28)Very good
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Parking
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      Pet friendly
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Perdido Sun Resort 7061 / 15
      (30)Very good
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Parking
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      Pet friendly
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      Great beachfront condo
      Reviewed 18 August 2015
      Great location with spectacular views of the Gulf of Mexico. Condo has everything you need for a quiet vacation. Great bed. Publix and Winn-Dixie about 1 mile away. National...
      Great facility, mediocre service.
      Reviewed 4 June 2015
      We love Perdido area and Perdido Sun. Great location, front desk helpful, facilities and condo 706 super. Not so thrilled with agency handling 706 for owners. Wrong info re...
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Serenity Now 13ad1 / 12
      (14)Excellent
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      Amenities & Details
      • Private Outdoor Pool (Heated)
      • Hot Tub
      • Parking
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Grand Caribbean West 308 by PKRM1 / 20
      1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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      • Hot Tub
      • Shared Outdoor Pool (Unheated)
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      Pet friendly
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      Smoking allowed
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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      The Parrot Perch 6au1 / 26
      (23)Very good
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      Amenities & Details
      • Private Outdoor Pool (Heated)
      • Hot Tub
      • Parking
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      Pet friendly
      Kid friendly
      Smoking allowed
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Hakuna Matata 23c1 / 19
      (32)Very good
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Parking
      • Private Outdoor Pool (Heated)
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      Pet friendly
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      Smoking allowed
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Cozy Hideaway 22c1 / 15
      (7)Very good
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Private Outdoor Pool (Heated)
      • Hot Tub
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      Pet friendly
      Kid friendly
      Smoking allowed
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Bahama Mama 18cd1 / 12
      (33)Very good
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      Amenities & Details
      • Hot Tub
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      • Private Outdoor Pool (Heated)
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      Pet friendly
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      Smoking allowed
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Dues Paid 32c1 / 19
      (19)Excellent
      2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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      • Parking
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      • Private Outdoor Pool (Heated)
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      Pet friendly
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      Smoking allowed
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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      Grand Caribbean West 309 by PKRM1 / 21
      1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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      • Parking
      • Shared Outdoor Pool (Unheated)
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      Pet friendly
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      Location Information
      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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      Perdido Skye Resort 531 / 16
      (2)Very good
      1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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      • Shared Outdoor Pool (Unheated)
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      Pet friendly
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      Smoking allowed
      Great place to stay
      Reviewed 9 July 2013
      I stayed here back in May. The place was perfect for a family of four. Our ten year olds especially enjoyed the bunk beds and the master bedroom was huge! Any and everything we...
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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      Life's A Beach 15a1 / 20
      (24)Very good
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Hot Tub
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Beach Colony Resort Gulf-Front Condo – Breathtaking Views!1 / 24
      (1)Excellent
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Washer
      • Air Conditioning
      • Waterfront
      • Shared Outdoor Pool (Unheated)
      • Cable/satellite TV
      • Wi-Fi
      • DVD Player
      • Hot Tub
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      Everything you’ve been dreaming of for your beach vacation is reality at Beach Colony Resort, a luxury getaway loaded with amenities. At our 2BR/2BA condo, you’ll soak up picturesque views of sandy shores from nearly every room and feel the Gulf of Mexico breeze on your private balcony. Onsite...
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      Pensacola, Florida Panhandle 32507
      Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Toes In The Water 46cu1 / 12
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      Location Information
      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Seaclusion 18a1 / 20
      (31)Very good
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Hot Tub
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Purple Parrot 12ad1 / 19
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Hot Tub
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Boogie Man 36c1 / 19
      (16)Very good
      3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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      • Private Outdoor Pool (Heated)
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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      Coastal Escape 17c1 / 21
      (16)Very good
      3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Private Outdoor Pool (Heated)
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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      Perdido Sun Resort 3121 / 27
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Private Outdoor Pool (Heated)
      • Hot Tub
      • Parking
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      Pet friendly
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      Smoking allowed
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Perdido Sun Resort 7041 / 22
      (20)Average
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Perdido Sun Resort 1108 by PKRM1 / 20
      (16)Excellent
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Private Outdoor Pool (Heated)
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      Pet friendly
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      Smoking allowed
      Beach Front Bliss
      Reviewed 17 June 2018
      Lovely week on this ocean front condo! Pictures are accurate. Everything you need in condo. Extra details not in other reviews: Each bedroom has direct access to the bathroom...
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Caribbean Soul 40c1 / 32
      (11)Very good
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Hot Tub
      • Private Outdoor Pool (Heated)
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      Pet friendly
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      Caribbean Soul is Perfect for a Family Vacation
      Reviewed 7 October 2015
      I don't think it can get much better than 40C at the Purple Parrot. The location is secluded and quiet, but a short walk to the pool and Tiki Bar. The owners have obviously...
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Mer'sea 21c1 / 24
      (15)Excellent
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      • Private Outdoor Pool (Heated)
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Perdido Sun Resort 308 by PKRM1 / 21
      (2)Average
      2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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      • Private Outdoor Pool (Heated)
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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      Southern Grace 34cd1 / 15
      (18)Excellent
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      Location Information
      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Best Views in Orange Beach1 / 8
      4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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      • Wi-Fi
      • Air Conditioning
      • Secure Parking
      • Shared Indoor Pool
      • Cable/satellite TV
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      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      Welcome to the most luxurious and spacious condo in the absolute best location in Orange Beach. This condo features 3,400 square feet inside and a wrap around 1,800 square foot balcony that circles the condo. Every bedroom had balcony access. This unit can easily and comfortably handle a large...
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      Pensacola, Florida Panhandle 32507
      Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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      Parrot Bay 37cu1 / 14
      (10)Very good
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Hot Tub
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      The Sea Robin 11A1 / 24
      (40)Very good
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      Perdido Sun Resort 10061 / 9
      (31)Very good
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      Amenities & Details
      • Parking
      • Private Outdoor Pool (Heated)
      • Hot Tub
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
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      Location Information
      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Ocean Breeze East 404 by PKRM1 / 16
      3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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      Amenities & Details
      • Shared Outdoor Pool (Unheated)
      • Parking
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
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      Location Information
      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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      Perdido Sunrise 9b1 / 31
      3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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      Amenities & Details
      • Parking
      • Hot Tub
      • Private Outdoor Pool (Heated)
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
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      Location Information
      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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      Mediterranean at Perdido Key - Booking Up Fast - Open Fall Dates Reduced1 / 29
      4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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      Amenities & Details
      • Internet Access
      • DVD Player
      • Shared Outdoor Pool (Unheated)
      • Washer
      • Hot Tub
      • Air Conditioning
      • Cable/satellite TV
      • Waterfront
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      This spacious condo is approximately 3500 sq.ft. with spectacular views of the gulf and wraparound balcony. It features a gourmet kitchen with wine cooler, double-sided sub-zero refrigerator, and stainless steel appliances. The master bedroom is located oceanfront and is quite spacious with floor...
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      Location Information
      Pensacola, Florida Panhandle 32507
      Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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      Caribbean Queen 28cd1 / 10
      (2)Excellent
      1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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      Amenities & Details
      • Hot Tub
      • Parking
      • Private Outdoor Pool (Heated)
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      View all property information
      Location Information
      Pensacola, Florida Panhandle 32507
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
      Make Enquiry
      1
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