
Vacation rentals with a pool in Santa Rosa Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Santa Rosa Island
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Gulf Views on private beach Nov/Dec $500/week
Nov/Dec - $500/weekly rate (minus fees) not holidays. **Jetty East is replacing the stairwell starting mid-Oct, expected to last until Spring.** Begin your vacation at this 1-bed and 1-bath that sleeps 4 guests located on 5th floor. We are located directly on the private beach with views of jetties, harbor, and the Gulf. Centrally located in the heart of Destin near restaurants, shopping and exciting events before retreating back to your condo to unwind on the balcony while enjoying the view.

Relaxing Gulf Front Couple's Retreat*Beach Service
Welcome to Okaloosa island! Come experience gorgeous Direct Beachfront unobstructed views! This studio has everything you need for a fabulous beach getaway! Private balcony. Just seconds to beautiful beach & Gulf. 2 Chairs & Umbrella have been purchased for you w/ full beach service$50/day value (Mar-Oct)for a beautiful beachy day! 4 min drive to dining. Lg pool. LVP flooring*2022*Couch*2022*Premium foam mattress*2022 Spotless w/Low Cleaning Fee! Must be 22 years old to book w/ proof of ID

1004 Oceanfront Pelican Beach Fab Loc Pools/HTubs
1 Bed 2 Bath (Sleeps 6) NO PETS! Non-Negotiable rates. Location! Easy access to attractions! Direct access on the beach without having to cross the street. Pelican Beach Resort 1004 is a newly renovated 1-bedroom condo with stunning Gulf of Mexico views from your private balcony, an open-concept living area, and comfortable sleeping accommodations for up to 6 guests The fully equipped kitchen is designed with a bar that overlooks the living area for entertaining or enjoying a casual meal.

Amazing Top-Floor Condo, Free Beach Service!
Decorated in soothing designer colors with a coastal feel, the unit has 2 bedrooms with comfortable king size beds, flat screen TVs and private bathrooms; two bunk beds in a hallway alcove; 2.5 bathroom, and open concept full size kitchen with all new full size stainless steel appliances, dining area and living room with a sleeper sofa. The unit sleeps eight. Plus, you'll have access to all of Waterscape Resort's fabulous amenities! Complimentary beach service with 2 beach chairs and umbrella.

Beachfront! Newly remodeled! Right on the beach!
Beachfront top floor unit, on a private beach, in two story building gives unobstructed sunset/ocean views. Located on soft white sand with on-site free parking. Perks of choosing this unit include gated resort with pools, beach service included (Mar.-Oct.), tennis courts, pickle ball, and par 3 golf course (included). Unit has fully functional kitchen and wifi included. Master bedroom beach/sunset views! Sleeps 4 adults with use of sofa bed in living area and additional cot-sized bunkbeds.

Oceanfront 3BR/3BA Condo | Steps to Sand & Surf!
Experience the Gulf in a Newly Remodeled Condo! This family-friendly ground-floor unit offers ultimate convenience. The master bedroom has ocean views, a king bed with a pullout trundle. The second bedroom has a king bed with a trundle, and the third has a queen bed. The living room includes a queen sofa bed. Each bedroom has a private bath and TV. Enjoy free beach service March–Oct with two chairs & an umbrella. Step onto the sand, relax, and unwind! Guests 27+ only. No smoking. No parties

Cozy Soundside Condo - WataView2!
Vacation or work at our comfortable waterfront kitchenette studio in the heart of Fort Walton Beach. The sugar white sand beaches are just a short drive away, and adventure awaits right at your doorstep on Santa Rosa Sound. Includes pool and marina! Boat slip (28 Ft) available! The unit has a queen bed and futon that lays down to a full size bed. It's very comfortable for small groups. We are real owner-hosts and strive to keep our unit spotless and well supplied for our cherished guests.

Waterscape 5th Flr -Closest 1 Bedroom to the beach
Enjoy the best courtyard and ocean views from this 5th-floor 1BR condo, the closest 1-bedroom unit to the beach at Waterscape Resort. The master bedroom features a king bed and en-suite bath. Kids love the bunk beds with TVs. The unit also includes a sofa bed, stainless steel appliances, in-unit washer/dryer, and beach chairs with umbrella stored in the unit. Guests return year after year for the views, comfort, and resort amenities like pools, waterfall, and lazy river.

Majestic Sun Ocean view 1 Bedroom Condo
This Majestic Sun 1 bedroom condo is located across the street from the beach with unobstructed Gulf views. It is conveniently located within the Seascape Resort. Perfect for those looking to vacation within the heart of Miramar Beach while enjoying a stunning ocean view. The complex amenities include an indoor/outdoor heated pool, hot tub, and well equipped fitness center. Snowbirds if please inquire for monthly rates. **MUST BE 25 YEARS OF AGE TO BOOK PER HOA RULES**

Island Princess 618 | Gulf Views & Beach Service
Experience the perfect beach escape in our beautifully renovated beachfront condo on stunning Okaloosa Island. This inviting retreat offers two spacious bedrooms, two modern bathrooms, and a rare oversized balcony—ideal for relaxing while taking in breathtaking Gulf views. Step onto the sugar-white sands and enjoy the emerald-green waters with complimentary beach service, including two chairs and an umbrella, provided from March 1 through October 31.

Okaloosa Island Gulf View Resort Studio w/ Balcony
Escape to the stunning white sand beaches of the Gulf of Mexico and stay in this charming studio condo on Okaloosa Island! Located in the popular Islander Beach Resort, this unit is newly renovated and boasts breathtaking views of the emerald green waters. Step outside onto your private balcony to watch the sunset or enjoy your morning coffee with the sound of the waves. Book your stay today and experience the best of the Florida panhandle!

Sleek & Sexy @ Sandestin Golf & Beach Resort
Newly remodeled pool & hot tub are now open!! TOP RATED 6th floor oceanfront studio at Sandestin Golf & Beach Resort's Beachside Two complex. Guests can enjoy dining, retail, entertainment, golf, tennis and other activities without leaving the gates of this 2400 acre resort on Florida's Emerald Coast. Sandestin Tram pass included. This property is highly ranked amongst Airbnb's Top 10% of homes based on ratings, reviews, and reliability.
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Destin Retreat: Oceanview Poolside Luxury Condo

Santa Rosa Beach Canopy House with heated pool

Book Holiday! Private Beach, Heated Pool, 2 Kings!

Sugar Sand Cottage at Destin Pointe

Coastal Retreat in Emerald Shores • Private Beach

Waterview Villa-Steps to the Sand-Pool-King Bed

Private Pool - Golf Cart - Block to Beach - Destin

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A
Condo rentals with a pool

Retreat by the Sea at Seacrest Condo

3 Min Walk to the Beach, Beach Svc, Sandpiper Cove

Sea Shell at Sunset Cottages - Beach Service Inc

3107 New Year's Eve ~ Heated Pool ~ Book Dec 31st

18th Floor Pelican Beachfront with Ocean View

Dream Beach Cozy Stay 3-Min walk to Miramar Beach

Zen Retreat ON Beach, Golfcart* Hot Tub, SanDestin

Free Chair Service-Beachfront 4th Floor
Other vacation rentals with a pool

Casa brezza estiva beach view

Pool Table, Lazy River & AmazingViews! Destin West

Resort Condo Heated Pool Ocean View Hot Tub Tennis

314 Island Princess - Beach, Pool, Spa, Balcony!

Modern Condo near Downtown FWB/Destin

Destin West Villa PH04~ Hot Tub,on Rooftop Terrace

Destin West Penthouse Bay, Roof Top terrace

Gulf View Island Studio w/ Restaurant Nearby
When is the best time to visit Santa Rosa Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ566 | ﺩ.ﺇ606 | ﺩ.ﺇ797 | ﺩ.ﺇ826 | ﺩ.ﺇ845 | ﺩ.ﺇ1,047 | ﺩ.ﺇ1,120 | ﺩ.ﺇ790 | ﺩ.ﺇ698 | ﺩ.ﺇ709 | ﺩ.ﺇ580 | ﺩ.ﺇ558 |
| Avg. temp | 12°C | 14°C | 17°C | 20°C | 24°C | 28°C | 29°C | 28°C | 27°C | 22°C | 16°C | 13°C |
Quick stats about vacation rentals with a pool in Santa Rosa Island

Total vacation rentals
Explore 2,550 vacation rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 55,400 verified reviews to help you choose

Family-friendly vacation rentals
1,850 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 110 rentals that welcome pets

Rentals with dedicated workspaces
1,680 properties have a dedicated workspace

Wi-Fi availability
2,550 of Santa Rosa Island vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Santa Rosa Island rentals

4.7 Average rating
Santa Rosa Island stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Santa Rosa Island's top spots, include Destin Harbor Boardwalk, Crab Island, and Gulfarium Marine Adventure Park
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- Crab Island
- Destin Harbor Boardwalk
- Opal Beach
- Princess Beach
- Frank Brown Park
- Navarre Beach Fishing Pier
- James Lee Beach
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- Tiger Point Golf Club
- Pensacola Beach Crosswalk
- Gulfarium Marine Adventure Park
- Eglin Beach Park
- Fort Walton Beach Golf Course
- Raven Golf Club
- Walton Dunes Beach Access
- The Track - Destin
- Camp Helen State Park
- Pensacola Dog Beach West
- Fred Gannon Rocky Bayou State Park
- Shipwreck Island Waterpark
- Seacrest Beach
- Gulf Breeze Zoo




