
Holiday rentals with a pool in Santa Rosa Island
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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.

Incredible View | Beachfront | Hot Tub
PLEASE read listing for info on property improvement project ★ DIRECT 5th Floor View of the Beach ★ Outdoor Pool ★ Free Parking ★ Outside Tiki Bar ★ On-Site Spa ★ Upgraded FAST Wi-Fi ★ Gym ★ Smart TVs & Cable ★ Gas Grills ★ Hot Tub ★ Beach Chairs ★ Beach Shop & Restaurant On Site ★ Steps to SunDestins private beach SunDestin Unit 506 Please read the entire listing before booking Thank you!

Waterfront cozy condo with king bed & resort pool
Welcome to The Salty Pirate, your waterfront vacation paradise! Kick back & relax in our calm, stylish condo featuring a king size bed, luxury bathroom & kitchenette. Relax in bed, enjoy the boats cruise by or watch the 65 inch TV. The waterfront balcony entices you to read & relax. Enjoy the resort style pool or reserve the 2-seater kayak (when available) provided for you to explore the waterway. Downtown restaurants & bars are walking distance & the white sugar sand beaches are 2 miles away!

Destin West Villa #V502 Beach Vacation Awaits
Newly updated beach-side 5th floor unit. Renovated bathroom with a large walk in shower. It has one of the best views in the Florida panhandle. A 180 degree view of the emerald waters of the Gulf of Mexico, the Okaloosa Island sand dunes, Destin and Choctawhatchee Bay. Your unit is Gulfside. You are steps away from the white sandy beach, 7 different pools and many restaurants and fun activities to walk to. Relax in the lazy river pool, sunbathe at the beach or spend your day being adventurous.

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 - WataView!
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.

Sugar Sand Cottage at Destin Pointe
This beautiful four bedroom beach cottage is located in the exclusive gated community of Destin Pointe. The home offers a tranquil setting and unsurpassed amenities that include a private lakefront pool for relaxation and entertainment-perfect for sipping your evening cocktails while overlooking the lake, direct lake views for the multiple levels of decks, private beach access to the sugar sands of Destin, and three community pools (one with a hot tub and splash pad) for guests use.

Retreat by the Sea at Seacrest Condo
Welcome to Retreat by the Sea. This studio is at Seacrest Condominiums located directly on the beach on beautiful Okaloosa Island in Fort Walton Beach six miles from Destin. Relax on the balcony and enjoy the beautiful views of the Gulf and amazing sunrises and sunsets. You have direct access to the beach and all the amenities that the condo has to offer including indoor/outdoor pool, gym and bbq area. This amazing studio also has a kitchenette, mini-refrigerator and private laundry.

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.

Waterscape A207/Free BCH SVC/2Kings/75' TV
Waterscape Resort A207 (just steps to the beach & pools) ~ Ocean view from kitchen/Master BRs/living room/patio ~ FREE beach service (2 CHRs+umbrella) during 3/1-10/31 ~ 2 King BRs with their own en suite + 1 half bath in the living area ~ One bunk room with a DOOR for privacy (two twin beds) ~ Q pullout sleeper ~ Pack 'n Play ~ Highchair ~ 4 smart TVs (1x75’’, 2x50’’, and 1x32’’) ~ Upgraded appliances & quartzite countertops ~ Tiles throughout ~ Washer/dryer in unit

Perfect View on Santa Rosa Sound with 2 Pools!
Enjoy beautiful blue skies and gorgeous sunsets over the Santa Rosa Sound, while looking out over the marina from your very own private deck! This gorgeous studio unit has one of the best views in the entire 120 room complex! Located in the preferred A building, this Non-Smoking, NO PETS ALLOWED, sparkling clean top floor unit has a beautiful bathroom with full size tile shower and newer plumbing fixtures. Marina slip is not available for rent at this time.

Islander Resort Okaloosa IsIand Beach Condo
Escape to Okaloosa Island and stay at this cozy studio condominium at the Islander Resort. This 6th-floor unit is perfect for couples or small families looking for a beach getaway. Wake up to stunning views of the Gulf of Mexico from the private balcony, relax on the pristine white sand beach, or take a dip in the Gulf-front pool. Take advantage of the resort's amenities, including a fitness center, shuffleboard, and barbecue grills.

"The Golden Sun" condo
"The Golden Sun." A luxury and calm stay in a 4th-floor condo only steps from the beach. Enjoy golden sunsets from the balcony that oversees the beach! Fast wifi with Alex integration(not offered by most condos). This features 1 bed and 1 sofa bed for a 4 person stay. 2 full bathrooms. A nice small kitchen so you can cook! Two TVs with Rokus for streaming. Small community grills for BBQ and a beautiful pool!
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Destin Retreat: Oceanview Poolside Luxury Condo

Private Heated Pool! Walk 2 Beach!

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

Tangerine Cove-5Min2Beach-Free golf cart Dec-Mar 1

Emerald Oasis: Hot Tub + Sleeps 18 + Pool+ Grill

#2 4BR HUGE PET Friendly Home Away from Snow!

Harbor Central Penthouse

Pet-Friendly-Pvt Heated Pool-Hot Tub-Fire Pit-6min
Condo rentals with a pool

3BR ~ Beachfront ~ Huge Balcony ~ 2 Pools ~ Luxury

Majestic Sun A711*Remodeled*Golf Cart*Heated Pools

Gulf View Studio condo Fort Walton Beach

Beachfront-Top Floor-West Corner-Free Bch Bch+ Gym

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

B103 Coastal Connection at Pirates Bay

Star Of The Sea

Waterscape Resort! Beachfront 1st floor oasis
Other holiday rentals with a pool

Located on the Water | Near Destin | Downtown FWB

Family friendly condo short walk to the beach!

Beach condo with Gulf view, heated pool and gym!

Destin West Villa PH04~ Hot Tub,on Rooftop Terrace

Gulf View Island Studio w/ Restaurant Nearby

Waterfront 1-Bdr Private Balcony

Beachfront - Amazing View - Newly Remodeled!

Pristine Pool and Water View!
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 | $268 NZD | $287 NZD | $378 NZD | $392 NZD | $400 NZD | $496 NZD | $531 NZD | $374 NZD | $331 NZD | $336 NZD | $275 NZD | $265 NZD |
| 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 holiday rentals with a pool in Santa Rosa Island

Total holiday rentals
Explore 2,620 holiday rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island holiday rentals start at $70 NZD per night before taxes and fees

Verified guest reviews
Over 55,720 verified reviews to help you choose

Family-friendly holiday rentals
1,900 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 130 rentals that welcome pets

Rentals with dedicated workspaces
1,570 properties have a dedicated workspace

Wi-Fi availability
2,610 of Santa Rosa Island holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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, Gulfarium Marine Adventure Park, and Crab Island
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- Point Washington State Forest
- Destin Beach
- Aqua Resort
- Crab Island
- Destin Harbor Boardwalk
- WonderWorks Panama City Beach
- Opal Beach
- Pensacola Beach
- Frank Brown Park
- MB Miller County Pier
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- The Track - Destin
- Gulfarium Marine Adventure Park
- Camp Helen State Park
- Gulf Breeze Zoo
- Shipwreck Island Waterpark
- Gulf World Marine Park
- Tarkiln Bayou Preserve State Park
- Henderson Beach State Park
- Pensacola Museum of Art
- Pensacola Bay Center




