
Holiday 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.

Beach Penthouse on Okaloosa Island in FWB, FL
Unit 301 has the best views being it is an end unit on the top floor. It also feels very spacious with its vaulted ceilings and unique loft area. Sleeps up to 6 people. Queen bed in Master. Another Queen bed and bath in loft. One full size sleeper sofa in living room. Owners have used the unit for past 9 years and have just decided to offer it as a rental. Freshly painted, and updated with new carpets, floors, furniture and appliances. Unit has everything you need for a wonderful vacation.

GULF FRONT TopFloor Amazing VIEW Directly On Beach
Cozy oasis with a view that takes your breath away! You'll enjoy relaxing on the private balcony overlooking the ocean. King bed and twin pullout loveseat. Beautifully renovated kitchen and bath. Fully stocked kitchenette with granite countertops. The full sized refrigerator is a special perk in this Luxury Honeymoon suite. Charming coastal accents throughout. Special attention has been given to this unit to ensure everything is top notch with professional upgrades. Waves roll in, cares roll out

Beachfront Bliss! Gulf Waves at The Palms #201
Nestled on shimmering Gulf shores, The Palms #201 invites you to unwind with jaw-dropping oceanfront views. This 2-bed, 2-bath sanctuary is your ticket to an unforgettable coastal retreat. Steps from the water, this guest favorite blends relaxation and rejuvenation for a home-away-from-home feel. From March through October, we provide complimentary beach service with two chairs and umbrellaāa $40 daily value included free! Pure paradise is at your doorstep. Book this dream coastal escape today!!

Star Of The Sea
Welcome to "The Star Of The Sea", Island Princess #312. Enjoy Gulf front views of the aqua blue waters of the Gulf with its sugar sand beaches from our beautifully decorated condo. Private balcony with access from family room and Master Bedroom. Fully stocked kitchen to prepare fabulous meals while taking in the views of the Gulf from the kitchen and dining area. Both master suites boast of comfort and access to private baths with full shower and tub amenities. Flat screen TV's in every room.

Waterfront Studio ⢠Santa Rosa Sound ⢠Sunsets
Enjoy breathtaking views of the Santa Rosa Sound and marina from your private top-floor balcony in this waterfront studio. Whether you're sipping coffee at sunrise or watching vibrant sunsets each evening, this spot delivers unforgettable costal charm in a quiet, peaceful setting. Perfect for couples or solo travelers, the studio features a full bath with tile shower, well-equipped kitchenette and sparkling pool. Gulf beaches are a just a short drive away. Free parking and easy self check-in.

Luxury 1-bdrm Studio. 2 Pools/Sauna/Hot Tub/Beach
Newly renovated! - Welcome to The Oasis, a luxury beach studio at El Matador Condos on Okaloosa Island, Fort Walton Beach, FL. Be our guest at this beautifully decorated, clean, comfortable studio, ideal for small families, small groups, couples, singles, & business travelers. You'll have direct access to the private beach & all the amenities including a seasonally heated outdoor pool, Gulf view pool, hot tub, sauna, gym, tennis/pickleball & basketball court, BBQ areas, & a laundry room.

DestinWest Pelican Bayside, Lazy River, Hot Tub.
Master bedroom with bathroom, bunk room with bathroom (the bunk room has one bunk bed and no door), sofa sleeper. Balcony with lazy river and bay view. You will find everything here from Lazy River, seven pools (one heated, one with waterfall), hot tubs, zero entry pool, gym, bbq area. Next door is an arcade with virtual reality, bar and food. You have access to swim and play in both the ocean and the bay. It is a short walk to the Okaloosa boardwalk for shopping, restaurants and fun

One Step to the Beach!
"One Step to the Beach" Highlights: - Beachfront Condo at Surf Dweller - First Floor - Pull Up to the Front Door and Unload - Free āPlatinumā Beach Service: 2 Beach Chairs, Umbrella + Kayak / Paddleboard access (Mar-Oct) - Two Parking Spaces - 1 King Bed - Master Suite - 2 Queen Beds - Second Bedroom - Cable + Streaming - WiFi - Keurig and Drip Coffee Makers - Seasonal Heated Pool - Tennis/Pickleball Courts - Washer and Dryer in the Condo - Pack n' Play - Shopping / Restaurants Nearby

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.

Spacious, elegant, beachfront, w/office
* Huge oceanfront lanai * Free beach service April 1-Oct 31 *Adult/Kiddie pool; tennis *Private office space in the condo *High chair/pack-n-play *Huge 1453 sq ft *Fully stocked kitchen incl. air fryer *Near Destin but WAY less crowded *South facing for sunrise & sunset (seasonal) & sometimes dolphins! *Open the door to your private lanai for REAL white noise of the ocean waves

Ocean view condo, Lazy River & Beach, Destin West
From your unit on the Gulf side of the resort, enjoy the spectacular ocean view, award winning lazy river, and many pools in this family friendly Destin West Beach and Bay Resort with private beach. Your unit is a couple blocks from Gulfarium Marine Adventure park, where you can swimming with dolphins. Enjoy the Broadwalk Okaloosa Island with seaside shops, eats, and entertainment within a block. Okaloosa Island fishing pier is within 2 blocks for fishing enthusiasts.

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.
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Sugar Sand Cottage at Destin Pointe

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

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A

Harbor Central Penthouse

#1 4BR HUGE PET Friendly Home Away from Snow!

The Charleston Experience-Free PoolHeat N GolfCart

Pool Retreat Near Destin Beach

All you need! Location | Golf Cart | Walk to Beach
Apartment rentals with a pool

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

Veranda 102 - Direct Beachfront - Gulf Side Pool

Okaloosa Island condo *free beach service

Destin West V506 - Free Beach Service & Lazy River

Sunshine and beach time /Okaloosa Island

Gorgeous 2BR With Panoramic Water Views

Serene Panoramic Views of the Gulf

3BR ~ Beachfront ~ Huge Balcony ~ 2 Pools ~ Luxury
Other holiday rentals with a pool

Clean & Luxurious Beachfront ~ HotTubs+Gym+7 Pools

9 Unit Building, Private Pool, Gulf Front View

Gulf Dunes 506-Hello Sunshine | GulfFront+2 Pools

"SeaGlass" - Oceanfront with expansive balcony.

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

Beach Retreat

Stars & Seaā¢Overlooking Pool & Soundā¢Sleeps 4

Home on Bay-Private Pool-Boat Access-Kayaks-Fish!
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 | £116 | £124 | £164 | £170 | £173 | £215 | £230 | £162 | £143 | £139 | £124 | £121 |
| 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 £30 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 130 rentals that welcome pets

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

Wifi availability
2,610 of Santa Rosa Island holiday rentals include wifi 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 Islandās top spots include Destin Harbor Boardwalk, Gulfarium Marine Adventure Park and Crab Island
Destinations to explore
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- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Pensacola Beach
- Opal Beach
- Frank Brown Park
- Johnson's Beach, Gulf Islands National Seashore
- Navarre Beach Fishing Pier
- Blue Mountain Beach
- Grayton Beach State Park
- Gulf Breeze Zoo
- Camp Helen State Park
- Shipwreck Island Waterpark
- Henderson Beach State Park
- Gulfarium Marine Adventure Park
- Village of Baytowne Wharf
- The Track - Destin
- HarborWalk Village
- Gulf World Marine Park
- Topsail Hill Preserve State Park
- The Boardwalk on Okaloosa Island
- Aqua Resort
- Destiny East
- Johnson Beach




