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Holiday Rentals with Pools in Pensacola Beach

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    Travellers to Pensacola Beach are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    753 Matching Rentals in Pensacola BeachView all 957 rentals
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Palm Beach #254 Club:   Newer Renovation 3BR/3Ba, Your Well-Deserved Getaway!1 / 23
    (64)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    $99 per night - Pensacola Beach - free WiFi - ocean front - 20th floor1 / 20
    (83)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Your 'Beach Home Away From Home' Overlooking Pensacola Bay1 / 32
    (53)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Front Row seats to the Gulf of Mexico1 / 24
    (95)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    CLEAN and NEWLY Renovated!  Relaxed and Fun Decor.  2B/2B with W/D1 / 22
    (78)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Experience the Beach Life at Emerald Isle 12031 / 23
    (55)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful 'Bella Blue' Heated Pool, Elevator &  Best Location1 / 26
    (38)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Waterfront Home -Heated Pool, Close to Restaurants and Gulf1 / 50
    (36)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Fall Openings! Villas on the Gulf  3 min walk to the Beach 5 ⭐️ Reviews1 / 30
    (79)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    Amazing Views directly on Gulf - Renovated 2 Bedroom Condo Starboard Village1 / 24
    (47)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Summer Beach Blues - Spectacular1 / 46
    (34)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Portofino Island Resort... Luxury Resort & Spa1 / 24
    (58)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    'Apres Sea'...Emerald Isle Premier 14th Floor Gulf Front, Luxury Furnishings1 / 23
    (42)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Breathtaking Unobstructed Gulfront View in Tower 5 Portofino1 / 48
    (46)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Creating Memories to Last a Lifetime1 / 50
    (43)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    5 Star Gulf Front Condo on Pensacola Beach, Emerald Isle #12061 / 44
    (32)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Emerald Isle, 5 star, Free Lazy Days beach chairs & 1 hr. paddle board/kayak1 / 23
    (61)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Stars ⭐️ Gulf Front 9th Floor ‘Changes in Altitude’ Gulf Front Condo 2/21 / 47
    (59)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    'Our Happy Place' LOW Fall rates 3 min walk to the Gulf lots of  5 ⭐️ Reviews1 / 39
    (57)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Luxury Resort & Spa - Fantastic Gulf & Bay View1 / 30
    (34)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Seas the peace and tranquility!  Gorgeous sunsets! White sand for snow birds :)1 / 49
    (44)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Waterfront Home-Pool/Spa-Sleeps 21-100 ft dock, Indoor slide, Water Trampoline1 / 48
    (7)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 20 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 20
    Gulf Front Relaxation for Beautiful Fall Weekends1 / 24
    (47)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2br, 2 Bth, Gulf-front, sleeps 4-6, new furniture in living room and on balcony.1 / 22
    (33)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Renovated 2br/2.5ba Sleeps 7-Playstation 3 & Beach Chairs/Umbrella in Unit1 / 49
    (64)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 7
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    Gulf front 'Seas the Day' 2/2 Villas on the Gulf all new everything !1 / 49
    (66)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Portofino Tower 1-908 Gulf Front Sunrise Views- 9th Floor1 / 45
    (51)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Stunning Gulf And Beach Views From Tower 2 - 7th Floor1 / 22
    (36)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Escape to White sands and Emerald waters! Breathtaking views!!1 / 24
    (53)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    PORTOFINO TOWER 3 UNOBSTRUCTED GULF FRONT VIEW!  ALL INCLUSIVE PRICE -  (ELITE )1 / 50
    (46)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Beautiful Gulf Front 2 Bedroom  / 2.5 bath Beach Condo at Starboard Village 2241 / 24
    (98)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    SUMMER DATES STILL AVAILABLE1 / 26
    (82)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    20th Floor Condo w/ Gulf Front Views!1 / 22
    (133)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Spacious 2 Bedroom Condo at resort with Beach Access, Shared Pools, Spa and more1 / 24
    (27)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Incredible New 4br/3ba  Beach Front Town Home/Sleeps 12 with Hot Tub and Pool(s)1 / 48
    (18)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Free Beach Chair/Umbrella Service1 / 37
    (67)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Portofino Paradise. 2bd/2.5ba - Luxury Condo.  Unobstructed Gulf views.  T51 / 50
    (74)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    'Apres Sea'...Emerald Isle Premier 14th Floor Gulf Front, Luxury Furnishings1 / 23
    (42)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    Your Portofino Paradise Is Only A Phone Call Away! Tower 31 / 50
    (57)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    August Specials- Contact Mgr-Best view in the Regency towers1 / 41
    (26)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Gorgeous Condo directly on the Gulf of Mexico!1 / 47
    (36)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pensacola Beach, Florida Panhandle 32561 2069
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    On the Gulf of Mexico - Steps to the Beautiful White Sand and Emerald Green Wate1 / 39
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    RELAX, RECHARGE, CHILL-OUT! Beautiful sunsets and over 100 REVIEWS!1 / 21
    (72)Excellent
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    ‘Serenity Sound’  LOW 2019 Fall rates with Sound  View, Easy Gulf Access1 / 38
    (69)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Brand New Ocean/Sound Side Retreat...Best Sunset and Water Views On The Island!1 / 23
    (43)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    $95 February  Special...Hear OCEAN WAVES from Balcony !! Gulf View1 / 24
    (77)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola Beach, Florida Panhandle 32561
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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