
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.

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

Amazing View Beach Front Condo
2-bedroom, 2-bath unit is located on 4th floor of Island Princess condominium with amazing unobstructed views of ocean from living room and bedroom balcony. Free parking (Assigned covered parking) You can enjoy FREE BEACH SERVICE (2 chairs & 1 umbrella set up for you on the beach). Beach Service runs from Mar 1, through Oct 31st • 2 Queen beds, 1 Queen sleeper sofa, 1 Bunk (Total occupancy 7) . Fully equipped kitchen • Washer and Dryer • FREE Wi-Fi & Cable TV • Pool & Hot tub • Fitness center

ISLANDER BEACH 5TH FLOOR GULF VIEW CONDO - 2BD/2BA
Islander Beach Resort is a 7-story structure of 114 condos on a short 2 mile stretch of Okaloosa Island and sits DIRECTLY on the BEACH. The building is painted aqua blue and gray, and all units overlook the ocean. There are 2 elevators and lots of parking. Guests can freely access the beach, HEATED pool, BBQ pits and parking area (a parking pass is needed from lobby). You will probably spend a lot of your time on our large private balcony overlooking the pool and beach, listening to the waves.

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 umbrella—a $40 daily value included free! Pure paradise is at your doorstep. Book this dream coastal escape today!!

Destin West Penthouse Bay, Roof Top terrace
This fresh looking/newly remodeled Sandpiper PENTHOUSE Condo offers the best of two worlds. It offers breath taking, direct-shot views of the pristine Choctawhatchee Bay , Lazy River and Zero entry & seasonally heated Water Fall pool. The Hot tubs, New Marina and BBQ pits are right below your two balconies. This is a 1 Bedroom with Bunk Room and 2 baths Penthouse condo on the Bay side of Destin West. The views from the roof-top floor blow away the condos on the lower floors. On site Marina!

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.

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.

Tranquil & Pristine at El Matador Resort
Our top floor non-smoking beach condo has stunning water views from all windows. A fully-stocked kitchen, large dining room table with six chairs, comfortable living room, bedroom furniture and Smart tvs, will make your visit a delight. Enjoy the sights and sounds from our balcony and the afternoon sun after a day at the beach. Chairs and beach equipment is in our balcony closet for your use. Two elevators are available in our building and a washer and dryer on each floor. Good times!

Lovely beach-front condo with free beach setup.
As soon as you enter our 3rd floor beachfront condo, you will leave all your cares behind and unwind while enjoying a direct view of the Gulf of Mexico. You can walk to the beach straight out of the building, no need to cross any roads. Many updates done in March 2021: brand new queen size sleeper sofa bed, brand new stainless steel refrigerator, range, dishwasher and microwave, brand new furniture, new paint, new flooring, and brand new TV's. We have Netflix and high speed WiFi.

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

2 min walk to Beach/Free Beach Service/Pool
Elevate your vacation experience with a stay at the Beach Hive! Conveniently located less than 2 minutes from the shores of the Gulf. Complimentary beach service (2 beach chairs and 1 umbrella) is available from 3/1-10/31. Escape the crowd & enjoy time at the Beach, lay by the pool or visit all that Okaloosa Island & the Emerald Coast have to offer. Then, return to this modern beach cottage to wind down and relax in style and comfort after a long day.
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Destin - Beach and Gulf View - 5A

Sugar Sand Cottage at Destin Pointe

Coastal Retreat in Emerald Shores • Private Beach

5 BD Miramar Beach House| Walk to the Beach + Pool

Harbor Central Penthouse

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

Pool Retreat Near Destin Beach

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

The Merry Whale on The Emerald Coast

Pool Table, Lazy River, & HUGE Patio! Destin West!

Retreat by the Sea at Seacrest Condo

Sea Oats*Beachfront View!2Bdr/2Bath, Sleeps 6

DestinWest Pelican Bayside, Lazy River, Hot Tub.

Gorgeous Gulf Front condo with amazing views!

One Step to the Beach!

Gorgeous 2BR With Panoramic Water Views
Other holiday rentals with a pool

Seaside getaway !

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

Emerald "Jule"' - Waterfront Villa 19B

Destin West Sandpiper 407 - Resort Style Condo

Lazy River Bliss @ Destin West — 1 BR + Bunk Room

Gulf View Island Studio w/ Restaurant Nearby

Serene Panoramic Views of the Gulf

New! Bluefish Paradise 2BR
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 | £115 | £123 | £162 | £168 | £172 | £213 | £228 | £161 | £142 | £138 | £123 | £120 |
| 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 Island’s top spots include Destin Harbor Boardwalk, Gulfarium Marine Adventure Park and Crab Island
Destinations to explore
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- Rentals with pools Okaloosa County
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- Rentals with pools United States
- 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
- Gulf World Marine Park
- HarborWalk Village
- Topsail Hill Preserve State Park
- The Boardwalk on Okaloosa Island
- Aqua Resort
- Destiny East
- Johnson Beach




