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Holiday Rentals with Pools in Pensacola

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    $203 Average
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    Travellers to Pensacola are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    15 Matching Rentals in PensacolaView all 33 rentals
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    ROMANTIC Beach Getaway for Couple!1 / 45
    (20)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    $199/night  Brand New Interior, many upgrades1 / 23
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Top floor, end unit , beautiful beachfront view1 / 8
    (9)Very good
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    WAY COOL 7C1 / 13
    (8)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • Terrace
    • Air Conditioning
    • Balcony
    • Grill
    • Parking
    • Private Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “WAY COOL” is one of our Three Bedroom Villas that will have you calling in back at work to extend your vacation... This refreshingly decorated piece of parrot-dice is one that is sure to please everyone in the family and is idea for those vacations that require a larger villa to fit the family....
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Lost Key-Great Beaches, Golf  & Weathe-- MUST BOOK--6NIGHTS Sat to Sat Stay1 / 54
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Ocean Views
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2017
    My family chose this rental because of the space and location. We had 9 in our group (2 teenagers, 6 adults and a 5-year old) and the space was perfect. Mary Jayne had...
    Reviewed 21 May 2017
    This was our first stay at a condo so we were very hesitant about doing this for the first time. I must say that this stay was the most relaxing and unforgettable experience...
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    About this property
    LOST KEY-- GREAT BEACHES, GOLF & WEATHER!! ! ****MUST BOOK ATLEAST 6 OR MORE NIGHTS!!!!*** (SAT TO SAT STAY!) **Great beaches, golf, scenery, & weather are just a few reasons why visitors choose our condo at Lost Key Beach/Golf Club for their peaceful vacation getaways. Lost Key is a low...
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    Pensacola, Florida Panhandle 32507
    Condo/Apartment - 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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    Amenities & Details
    • Grill
    • Balcony
    • Hot Tub
    • Parking
    • Internet Access
    • Terrace
    • Air Conditioning
    • Private Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 1 bedroom 1 bath upstairs condo at the Purple Parrot Village Resort located in a secluded area of the resort. This condo comfortably sleeps a family of no more than 2 adults and 2 children. The living room is equipped with a television, DVD player, wireless internet and a sleeper sofa....
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Perdido Skye Resort 251 / 15
    (3)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Balcony
    • Internet Access
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 February 2015
    We were disappointed in this unit but it is "ok" and the price is right. We talked with the management company and gave them a list of things that would improve the...
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    About this property
    This is a 1 bedroom 1 bath vacation home at the Perdido Skye Resort on the second floor with a Gulf front view. This condo comfortably sleeps a family no more than 6 people including all adults and children. The living room is equipped with a television, DVD player, internet and a sleeper sofa....
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    Location Information
    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 5 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
    VIRTUAL TOUR 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...
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    Pensacola, Florida Panhandle 32507
    Condo/Apartment - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    CARIBE CORNER 3A1 / 22
    (37)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Balcony
    • Parking
    • Grill
    • Air Conditioning
    • Terrace
    • Hot Tub
    • Private Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 2 bedroom 2.5 bath vacation home at the Purple Parrot Village Resort just steps from the outdoor pool. All of the condo buildings at the Purple Parrot Village Resort are two-stories and in this rental unit all the bedrooms are upstairs. This privately owned condo comfortably sleeps up to...
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    Location Information
    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    A COZY NOOK 13CD1 / 20
    (21)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Hot Tub
    • Parking
    • Private Indoor Pool
    • Internet Access
    • Balcony
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2015
    Great location between the Naval base and the resort. Minutes from the beach. Loved the Tiki bar.The House was a perfect size for me and my wife. Would come back again.
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    About this property
    This is a 1 bedroom 1 bath downstairs unit at the Purple Parrot Village Resort in a central location close to parking and a short walk to the pool. This condo comfortably sleeps a family of 2 adults and 2 children. The living room is equipped with a television, DVD and BluRay player, wireless...
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    Location Information
    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beach Colony Resort Gulf-Front Condo – Breathtaking Views!1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • 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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    Location Information
    Pensacola, Florida Panhandle 32507
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    BOOGIE MAN 36C1 / 19
    (16)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Hot Tub
    • Balcony
    • Terrace
    • Internet Access
    • Grill
    • Private Indoor Pool
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 3 bedroom 2.5 bath vacation home at the Purple Parrot Village Resort located in a secluded area of the resort. This condo comfortably sleeps a family of no more than 8 people including all adults and children. The living room is equipped with a television, DVD player, wireless internet...
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    Location Information
    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    RETURN TO ME 45C1 / 22
    (34)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Terrace
    • Grill
    • Parking
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Balcony
    • Private Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 2 bedroom 2.5 bath vacation home at the Purple Parrot Village Resort located in a secluded area of the resort. All of the condo buildings at the Purple Parrot Village Resort are two-stories and in this rental unit all the bedrooms are upstairs. This privately owned condo comfortably...
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    Location Information
    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Shared Indoor Pool
    • Cable/satellite TV
    Suitability
    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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    Location Information
    Pensacola, Florida Panhandle 32507
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    SPECIALS! SNOWBIRDS! PIER WATERVIEW POOL NR PRIVATE BEACHES! NR NAS!1 / 49
    (28)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2017
    I loved my time in Pensacola! Beautiful city and lovely, relaxing beach! Renting this space really made my stay! Clean and inviting. Spacious kitchen and two bathrooms! It was...
    Reviewed 9 July 2016
    We really enjoyed at stay here, we were close to plenty of beaches and activities. On days when we didn't feel like getting out we had a wonderful pool within walking distance...
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    About this property
    SPECIALS! SNOWBIRDS BOOKING NOW TOO! RATES LISTED FOR MONTHLY ARE NOT CORRECT AND MUCH LOWER! $50 OFF IF BOOKING THIS WEEK FOR WEEKLY! See pricing at the bottom! Ad does not always reflect the current specials or correct info! Nightly is far less when renting for a week! We will give you whatever...
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    Location Information
    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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