Surfside Properties Vacation Rentals - Pensacola Beach, Florida

Surfside Properties Vacation Rentals - Pensacola Beach, Florida A unique and personal approach to vacation rentals in Pensacola Beach, Florida Surfside Properties specializes in properties on Ft.

Pickens Road located on the west end of the island. We meet each guest at the condo door to welcome them to Pensacola Beach and explain the amenities of the vacation rental property. We also share our favorite restaurants and attractions in Pensacola Beach and in Pensacola. Our hope is that this personal touch encourages our guest to return year after year to Surfside Properties and to Pensacola B

each
Search our condo listings from upscale to budget-friendly, traditional to modern, two bedroom properties up to larger three and four bedroom condominiums. Let us help you make your vacation memorable! The powdery, white sand beaches and emerald waters of the Gulf of Mexico is the perfect spot to relax and unwind. In addition to the miles of unspoiled beaches within Fort Pickens and the National Seashore, Pensacola Beach offers many family-oriented activities including miniature gulf, parasailing, jet-ski rentals and charter boat fishing. Every night you can dine at a different restaurant or visit one of Pensacola Beach’s hot spots like The Shaker, The Break, Bamboo Willie’s, or Captain Fun’s.

05/26/2026

🌴🎶 THIS WEEK AROUND PENSACOLA BEACH & DOWNTOWN PENSACOLA 🎶🌴
📅 May 25 – May 31, 2026

Looking for something to do this week? Here are some of the events happening around Pensacola Beach and Downtown Pensacola! ☀️🍹🎸

🇺🇸 Monday, May 25 (Memorial Day)
⚓ U.S. Coast Guard Barque Eagle public viewing downtown
🎶 Memorial Day live music and entertainment across Pensacola Beach and Downtown Pensacola

🎸 Tuesday, May 26
🎵 Bands on the Beach – Modern Eldorados
📍 Casino Beach Gulfside Pavilion
🕖 7 PM – 9 PM

🎶 Tuesday, May 26
🎤 Live music at Bamboo Willie’s on Pensacola Beach

🎹 Wednesday, May 27
🍹 Rosie O’Grady’s Dueling Piano Show
📍 Seville Quarter

✈️ Wednesday May 27-Friday May 29
💙 Blue Angels Practice Show
📍 Base
🕕 10:30-11:30

🎸 Thursday, May 28
🎶 38 Special Concert
📍 Saenger Theatre – Downtown Pensacola

🎷 Thursday, May 28
🎵 Live music at Five Sisters Blues Café

🎉 Friday, May 29
🎭 Grand Fiesta Parade celebrations & Seville Quarter after-parties downtown

🎹 Friday, May 29
🍹 Rosie O’Grady’s Dueling Piano Show
📍 Seville Quarter

🎸 Friday, May 29
🎶 Josh Strickland Trio live at Five Sisters Blues Café

🎬 Saturday, May 30
🍿 Movies in the Park – The SpongeBob Movie
📍 Hunter Amphitheater
🕕 6 PM

🍹 Saturday, May 30
🩸 Pensacola Bloody Mary Festival 2026
📍 Pensacola Beach
🕛 12 PM – 4 PM
🎶 Live music, vendors, food, raffles, games & more

🎨 Saturday, May 30
🌎 Gulf Coast Culture Fest 2026
📍 Seville Square
🕙 10 AM – 6 PM

🛍️ Saturday, May 30
🌿 Palafox Market
📍 Downtown Pensacola
🕘 Starts at 9 AM

☀️ Sunday, May 31
🎶 Waterfront dining, brunches, and live music throughout Pensacola Beach and Downtown Pensacola

🎵 Ongoing All Week:
🛥️ Pensacola Bay City Ferry rides & sunset cruises
🎤 Nightly live music at Pensacola Beach bars and restaurants

Tag someone you want to spend the week with in Pensacola! 🌊☀️

Some of our favorite photos are the ones shared by guests who have become part of our extended beach family over the yea...
05/22/2026

Some of our favorite photos are the ones shared by guests who have become part of our extended beach family over the years ❤️🏖️
We’re feeling extra grateful looking back at memories from some of our amazing snowbirds who have stayed with us year after year. From sunrise beach walks and shell hunting to sunset views and making lifelong memories, it’s been such a joy being part of your winter traditions.
Thank you for choosing us season after season and making our little slice of paradise part of your home away from home. We love seeing your smiles, adventures, and beach memories through the years ☀️🌴
To all our returning snowbirds — we can’t wait to welcome you back again soon! 🏝️❄️➡️☀️


https://www.surfsideproperties.com/

☀️ June beach dates are still available! 🌊🏖️Escape to Pensacola Beach next month and stay in this spacious 3 bedroom, 2 ...
05/15/2026

☀️ June beach dates are still available! 🌊🏖️
Escape to Pensacola Beach next month and stay in this spacious 3 bedroom, 2 bath vacation condo located in a gated community packed with amenities. Enjoy access to the pool, tennis courts, and bay access right on property — plus the beach is only steps away!
Spend your days soaking up the sun, exploring the island, or hopping aboard the FREE Pensacola Beach trolley, now running weekend service from 2PM–midnight. Even better, daily trolley service begins Memorial Day Weekend, making it easy to enjoy local restaurants, live music, shopping, and beach fun all summer long. 🚎🌴
Perfect for families, couples, or a last-minute summer getaway, this condo offers the ideal mix of relaxation and convenience in one of the best locations on the island.
Call us today for June availability and pricing before these dates are booked! ✨
surfsideproperties.com/listing/397711

🚨OPENING FOR BLUE ANGELS WEEKEND ✈️🌊A recent cancellation means this gorgeous gulf front 2 bedroom, 2 bathroom condo is ...
05/10/2026

🚨OPENING FOR BLUE ANGELS WEEKEND ✈️🌊
A recent cancellation means this gorgeous gulf front 2 bedroom, 2 bathroom condo is now available for the Blue Angels Air Show! Don’t miss your chance to experience one of Pensacola Beach’s most exciting weekends from the perfect location.
Watch the Blue Angels soar right from one of TWO private balconies, or step out onto the sugar white sand for a front row seat by the water. When the show is over, relax by the onsite pool or take a short walk to local favorite Peg Leg Pete’s for seafood, drinks, and island vibes. ☀️🍹
Whether you’re here for the air show, the beach, or both, this is the perfect spot for an unforgettable getaway.
surfsideproperties.com/listing/242103

05/08/2026

Just another morning on Pensacola Beach… or so we thought! 😎✈️ A couple of weeks ago, the Blue Angels made a surprise flyover—and, for a rare treat, the Thunderbirds joined in too. You always hear them before you see them!

🌴 June availability is calling at one of Pensacola Beach’s hidden gems! ☀️ Escape to this beautifully appointed 2 bedroo...
05/07/2026

🌴 June availability is calling at one of Pensacola Beach’s hidden gems! ☀️ Escape to this beautifully appointed 2 bedroom, 2 bathroom condo tucked inside a quiet bayside community — and the ONLY Signature Collection unit offered in the association.
Spend your mornings enjoying peaceful bay views, afternoons lounging by the on-site pool, and evenings taking a short stroll across the street to sugar-white sands and emerald Gulf waters. 🌊✨
Guests love the relaxing atmosphere while still being close to everything Pensacola Beach has to offer. Enjoy easy access to local favorites like Peg Leg Pete’s, waterfront dining, live music, beach bars, dolphin cruises, paddleboarding, fishing charters, and seasonal events happening all summer long. Looking for adventure? Take a scenic drive down to historic Fort Pickens National Park for bike trails, fishing spots, wildlife viewing, and some of the most beautiful untouched beaches on the Gulf Coast. 🚲🐬🏖️
Whether you’re planning a family getaway, couples trip, or peaceful beach retreat, this cozy coastal escape is the perfect place to slow down and soak up summer.
✨ Quiet community
✨ Bay access on site
✨ Community pool
✨ Short walk to beach access
✨ Signature Collection property
surfsideproperties.com/listing/391716

🌊 July Dates Available – Your Gulf Front Escape Awaits! ☀️Looking for the perfect beach getaway this summer? This stunni...
05/06/2026

🌊 July Dates Available – Your Gulf Front Escape Awaits! ☀️
Looking for the perfect beach getaway this summer? This stunning 3-bedroom, 3.5-bath Gulf-front condo is now available for select dates in July—and it’s everything you’ve been dreaming of.
Located in a gated community on the quiet west end of the island, this property is in the last Gulf-side association before Fort Pickens National Park, giving you a peaceful, uncrowded stretch of beach that feels like your own private paradise. 🏝️
Enjoy:
✨ Spacious layout with room for the whole family
✨ Private balconies with breathtaking Gulf views
✨ On-site pool and tennis courts
✨ A calm, relaxing atmosphere away from the crowds
✨ Quick drive to the main hub of island dining, shopping, and entertainment when you’re ready for fun
Whether you're sipping your morning coffee with the sound of waves or unwinding after a day in the sun, this is the kind of place that turns vacations into memories. 💙
📅 Limited July availability—don’t miss out!
surfsideproperties.com/listing/390519

🌊 Your Perfect Beach Getaway Awaits! 🌊Looking for the ideal spot to relax, recharge, and soak up those coastal vibes? Th...
05/02/2026

🌊 Your Perfect Beach Getaway Awaits! 🌊
Looking for the ideal spot to relax, recharge, and soak up those coastal vibes? This charming 1 bed / 1 bath first-floor condo has everything you need for the perfect escape!
✨ Sleeps up to 4 with a comfy pullout sofa
✨ Walk right out your sliding door and stroll down to the bay
✨ Beach access just a short walk away
✨ Located in a small, quiet bayfront complex
Enjoy the best of both worlds—you're just minutes from the island’s main activity hub, with dining, shopping, and entertainment close by… but far enough away to unwind in total peace when the day winds down.
Perfect for couples, small families, or a friends’ getaway 🏖️
With its adorable beachy decor, don’t be surprised if you start imagining making this your permanent home 💙
surfsideproperties.com/listing/236933

🌴✨ Your Perfect Beach Getaway Awaits! ✨🌴Looking for the ultimate mix of relaxation and fun? This beautiful 2-bedroom, 2....
05/01/2026

🌴✨ Your Perfect Beach Getaway Awaits! ✨🌴
Looking for the ultimate mix of relaxation and fun? This beautiful 2-bedroom, 2.5-bath townhouse-style condo has everything you need for an unforgettable vacation!
🏡 Spacious, multi-level layout with plenty of room to unwind
🌅 THREE levels of outdoor seating – perfect for morning coffee, sunset views, or evening cocktails
🏊‍♀️ Pool access on-site for easy, refreshing dips
⚓ Bay access + dock – bring your sense of adventure!
🏖️ Just a short walk to the beach
Enjoy being close to all the excitement, dining, and entertainment the beach has to offer—while still tucked away enough to relax and enjoy peaceful evenings under the stars.
Whether you're planning a family trip, a couples’ retreat, or a weekend escape, this is the spot you’ve been looking for!
surfsideproperties.com/listing/400144

Address

1200 Fort Pickens Road
Pensacola Beach, FL
32561

Opening Hours

Monday 10am - 8pm
Tuesday 10am - 8pm
Wednesday 10am - 8pm
Thursday 10am - 8pm
Friday 10am - 8pm
Saturday 10am - 8pm
Sunday 12pm - 6pm

Telephone

(877)2776875

Website

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