Vacation rentals with a pool in Santa Rosa County

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Top-rated rentals with a pool in Santa Rosa County

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Guest favorite

Condo in Pensacola Beach

4.98 out of 5 average rating, 105 reviews

Romantic Fall Getaway ~Stunning Views!

Stunning Beachfront View~Beautiful Interior Design~Beach Equipment~Chef's Kitchen~Ice Machine~Pool Experience the breathtaking beauty of Pensacola Beach with "Idle Wave," where you'll be enchanted by the stunning vistas of sugar-white dunes and the crystal-clear emerald waters of the Gulf. This inviting, family-friendly condo spans three floors, offering the ultimate escape for your upcoming vacation. Nestled on the serene side of the island, "Idle Wave" provides a peaceful oasis. With conveni

Guest favorite

Condo in Pensacola Beach

4.97 out of 5 average rating, 151 reviews

The Flamingo Flat @ Villas on the Gulf

🦩Welcome to the Flamingo Flat! PLEASE READ FULL LISTING. This airy, Palm Beach style condo is the perfect place to relax on a quiet stretch of Pensacola Beach. For great shopping, dining and entertainment you can drive ( less than 3 miles West) to the main hub of P’Cola Beach. Trolley service available during summer months. The beautiful Portofino Island Resort is just 1 mile to the East. MUST BE 25 TO RENT. NO CHILDREN UNDER 12. NO PETS. EARLY CHECK IN MAY BE AVAILABLE FOR AN ADDITIONAL $50.

Guest favorite

Home in Pace

4.92 out of 5 average rating, 168 reviews

THE PINE HOUSE Luxury, Romantic, Unique Retreat.

Enjoy this UNIQUE retreat! Located on 3 acres of lush pines, this home is the perfect getaway for you or your family. With the romantic modern vibe of the house, you are sure to feel RELAXED, REJUVENATED and ready for whatever is next. Cool the day off in our backyard SITTING POOL, or read a book in our 7 ft SITTING WINDOW. Watch the pines sway through our living room observing windows or have friends over for dinner at our outdoor dining area! No matter the reason, the Pine House is for you!

Guest favorite

Condo in Pensacola Beach

4.95 out of 5 average rating, 122 reviews

$0 clean fee! Beachside/pool view/king bed/jacuzzi

Perfect little place for couples or small families to get some R&R. This condo has a poolside view in a lovely little complex, and is just one building back from the beach - steps from paradise! The Gulf boasts some of the most beautiful beaches in the world, and this is the perfect location tucked away from the busy crowds but still close to restaurants, activities, live music, national parks, and a world class spa. The condo is well-equipped and recently updated in October 2022. Come enjoy!

Guest favorite

Condo in Pensacola Beach

5 out of 5 average rating, 128 reviews

Stay at Sunshine Daydream on Pensacola Beach

Come experience vacation paradise at "Sunshine Daydream" Located in the heart of Pensacola Beach. Perfect beaches, fantastic restaurants/bars, and shopping are only steps away. Enjoy pristine views of Little Sabine Bay from all over this magnificently renovated condo. Unwind on the 300 sq ft covered balcony and watch the sunset from the best location on the island! The complex hosts a large heated swimming pool, private beach, exercise room, dock, elevators, and a full time cleaning staff.

Guest favorite

Condo in Pensacola Beach

4.98 out of 5 average rating, 173 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

**Recently Updated Interior!** Experience the stunning Gulf of Mexico from the comfort of this beachfront 2-King bedroom, 2-bath condo located directly on Pensacola Beach! Nothing separates you from the best white-sand beach on the Gulf Coast. This beach condo boasts a vibrant interior filled with beach-themed accents, a private balcony with sweeping ocean views, and access to 2 pools (1 heated) and a hot tub. Enjoy the best restaurants and shopping on the beach, all within a short walk.

Guest favorite

Guest suite in Gulf Breeze

4.95 out of 5 average rating, 118 reviews

Cozy Suite | 2BD/1BA | Private Pool and Backyard

Welcome to Bella Blue! Our beautiful and newly renovated Pool Oasis. Quiet private 2 BR / 1 BA apartment with a private crystal clear pool/ inviting firepit and more. Private fenced spacious backyard for pets. Only 6 Miles from beautiful Navarre beach. Hang out in our family friendly play pool or head to the emerald waters of Navarre beach. Located one mile from the Gulf Breeze Zoo, 15 miles from Pensacola Beach. Conveniently located for shopping /restaurants. We hope you enjoy! - Sonya

Guest favorite

Condo in Pensacola Beach

4.88 out of 5 average rating, 120 reviews

Sugar Sand Beach Retreat at Villas on the Gulf

Welcome to Sugar Sand Beach Retreat! You're just a lovely stroll away from the white Sugar Sand beach & gorgeous emerald water of the Gulf of Mexico, ranked #1 Florida Beach in USA Today's 10 Best Reader's Choice Award, 2018 and #4 Best Beaches in America by TripAdvisor, 2019. Our 2 bedroom condo with private entrance & covered parking,comfortably sleeps 6. Enjoy the beautiful foliage on your private balcony overlooking the pool. Or relax by the lagoon to watch the ducks and turtles.

Guest favorite

Condo in Pensacola Beach

4.95 out of 5 average rating, 110 reviews

Sea-Esta Beach Front 2 Free Chairs, Umbrella, Pool

Stunning oceanfront condo located directly on Pensacola Beach. Free Beach Chairs and Umbrella. Free WiFi Master bedroom w king bed and Guest bedroom w two double beds. Full bath in the master and beautiful full walk in shower in guest room. Updated fully equipped kitchen w granite countertops and new stainless steel appliances. Start your day watching the sun rises from your balcony over the Gulf of Mexico and end it watching the sun set over another day in Paradise!

Guest favorite

Condo in Pensacola Beach

4.94 out of 5 average rating, 231 reviews

Newly renovated condo with amazing water views!

Experience the clear blue water and white sand of Pensacola Beach. Enjoy spectacular views of Pensacola Bay from a private 3rd floor balcony. This newly renovated condo offers a fully stocked kitchen, luxury linens, and calming beach decor. The master has a queen size bed, flat screen TV, and ensuite bathroom. The 2nd bedroom offers 2 full size bunk beds. The main living room has another flat screen TV, comfortable couch and is a perfect place for your group to gather.

Guest favorite

Condo in Pensacola Beach

4.92 out of 5 average rating, 103 reviews

Gulf front @ Emerald Isle! Heated Pool! Sleeps 6!

Welcome to The Diving Dolphin... a 2 bedroom/ 2 bathroom condo located in Emerald Isle Condominium complex~ Directly on Pensacola Beach! This beautiful condo is located on the 5th floor and overlooks the stunning waters of the Gulf of Mexico! Come on in and relax- this condo has it all! The condo has a capacity to comfortably sleep 6. We will send you a welcome packet with details about the complex, unit and area! ~COMPLIMENTARY BEACH CHAIR SET UP MARCH - OCTOBER!~

Guest favorite

Tiny home in Pensacola

4.96 out of 5 average rating, 113 reviews

Tiny Home Pool view 25 Mins to Beach -Unit A

Welcome to our cozy tiny home located in my secured backyard, where a queen-sized bed promises a peaceful night’s sleep and our well-equipped kitchenette simplifies meal preparation. You will have free parking in the backyard located just steps away from the tiny home. Additionally, you’ll have the opportunity to gather around the outdoor fire pit for cozy evenings under the stars. Inside, unwind with a smart TV and stay connected with complimentary Wi-Fi.