
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.

The Merry Whale on The Emerald Coast
Newly updated 1 bedroom/ 2 bath condo with built in bunkbeds. Located beach side on the 19th floor with breathtaking panoramic views of the emerald waters and pristine white sand beaches The Gulf of Mexico. Fully stocked kitchen with new granite countertops and slate appliances. Reliable fast high speed internet throughout. Resort amenities include a large pool and hot tub, a beachside tiki bar serving frozen drinks and beer. A fabulous cafe that serves hot breakfast, pizza, sandwiches & salads.

Gulf Views! • Bikes• Garage • Pool • Gated Beach
Welcome to Serenity, A Wave From It All! at Beach Resort in Miramar Beach. Make memories while enjoying glistening views of the Gulf from this stylish 4th floor condo. Located directly across the street from the white sand beaches and Emerald Green shore line of Destin and perfectly situated near beach-front restaurants, world class shopping, stunning golf courses and endless entertainment options. 20-min to Crab Island and the Harborwalk. 15-min to SanDestin/Baytowne Wharf 40-min to airport

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.

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!

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.

Steps from Sand - Fort Walton Beach
Welcome to the Nautilus on Okaloosa Island! Enjoy an ocean view from this 2nd floor balcony where you are only steps away from sugar white sand beaches. This two bedroom, two bath condo is the perfect place for your beach vacation. The unit has everything you need, including a washer and dryer. Enjoy the nearby restaurants, shopping and heated pool. This destination will not disappoint! On-site amenities included: Heated pool Private beach access Complimentary Parking BBQ Grills And more!

Relaxing 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.

Cheery Condo-Free Beach Service-Direct Ocean View!
Let your cares literally drift away in this relaxing, kid-friendly, beautifully decorated condo with a King bed w/bath + twin/twin bunk area w/bath - Queen LR sleeper sofa. Enjoy stunning views of the Gulf of Mexico and pool area from your private balcony. We invite you to enjoy your special vacation at this perfect Emerald Coast paradise. Free beach service (2 chairs and umbrella) is INCLUDED! (March 1-Oct 31). *Note - Okaloosa County Tourist Tax of 6% will be applied to this booking.

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.

Seas the View - Island Luxury
NEW Porcelain Tile flooring throughout entire unit! Welcome to Gulf Dunes 105 on Okaloosa Island: - GULF-FRONT & BEACHFRONT - balcony GULF view - Free Beach Service (Mar - Oct) LOW density beach - Sleeps 6: 1 Bedroom: King Bed, Hallway Bunk, Sleeper Sofa - Heated pool 84-86 degrees (Nov-March) The perfect island getaway, for couples and small families, on the emerald waters and white sugar sands of Okaloosa Island. From dusk till dawn, experience the island’s breathtaking beach.

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/2 Kings/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
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Santa Rosa Beach Canopy House with heated pool

Walk to Beach · Private Heated Pool · Fenced Yard

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

Private Pool - Golf Cart - Block to Beach - Destin

6-Seater Golf Cart with Bay, Lake & Golf View Home

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

Cottage House 4bd/3bath off 30A

#1 4BR HUGE PET Friendly Home Away from Snow!
Condo rentals with a pool

Destin West Villa PH01 ~ Penthouse w/ Hot Tub

Tropical Isle 215 - Steps to the Beach!

Spacious, elegant, beachfront, w/office

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

Lovely beach-front condo with free beach setup.

2 Bedroom Condo on the Beach at Okaloosa Island

Sunset Dreamin! Come join us for some R&R

Waterfront 1-Bdr Private Balcony
Other vacation rentals with a pool

Spacious 2BR Oceanfront | Balcony | Pool | Hot Tub

Crystal Sands 311B - Beachfront Free Beach Service

"SeaGlass" - Oceanfront with expansive balcony.

Serene Condo w/ Shared Pool, Hot Tub & Bch Access

Stars & Sea•Waterfront Condo•Updated•Sleeps 4

The Funky Monk

Gulfside Gem V306 (Heated Pool & Hot tubs)

Gulf Dunes 401 - Ocean Eyes
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 | G$32,177 GYD | G$34,475 GYD | G$45,340 GYD | G$47,012 GYD | G$48,057 GYD | G$59,549 GYD | G$63,727 GYD | G$44,923 GYD | G$39,699 GYD | G$40,326 GYD | G$33,013 GYD | G$31,759 GYD |
| 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 2,620 vacation rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island vacation rentals start at G$8,358 GYD per night before taxes and fees

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

Family-friendly vacation rentals
1,900 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
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 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, Gulfarium Marine Adventure Park, and Crab Island
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- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Opal Beach
- Pensacola Beach
- Frank Brown Park
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- Gulfarium Marine Adventure Park
- The Track - Destin
- Gulf Breeze Zoo
- Camp Helen State Park
- Shipwreck Island Waterpark
- Gulf World Marine Park
- Henderson Beach State Park
- MB Miller County Pier
- Village of Baytowne Wharf
- Destiny East
- The Boardwalk on Okaloosa Island
- Point Washington State Forest
- Aqua Resort
- Topsail Hill Preserve State Park




