
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.

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!

NAUTILUS 2608, Sleeps 6, Amazing Views!
Amazing views of the Gulf of Mexico from this 2 bedroom 2 bath condo, sleeps 6. On the 6h floor of the beautiful Nautilus condominium, you will enjoy the wide balcony with incredible views. Fully equipped kitchen, all linen and beach towels included. Beach service from March 1st until Oct 31st (2 chairs & an umbrella) Additional beach chairs and umbrellas in the condo. Heated pool. Many restaurants in the area. Groceries 5 min away. Special rates snowbirds and military on TDY. 25 yr old min.

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.

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.

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.

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.

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.

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.

Veranda 102 - Direct Beachfront - Gulf Side Pool
Small quaint 9 unit complex. Direct BEACHFRONT on the white sand of Okaloosa Island, FL. Completely remodeled! Breathtaking views of the emerald green waters of the Gulf of Mexico (and dolphins) right from the private patio! Gulf side pool (not heated). Contactless check-in. Walk 1 mile to the Pier & Boardwalk and restaurants. 15 minutes to Ft. Walton Airport. 2 person beach service (1 umbrella & 2 chairs) available 3/1 - 10/31

"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 Beach Access–Pool/Spa–Sleeps 14–Pets OK

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

Private Pool - Golf Cart - Block to Beach - Destin

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

Destin's most adored home!

The Charleston Experience-Free PoolHeat N GolfCart

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

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

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

Majestic Sun B211*Golf Cart Included*Heated Pools*

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

Marcel: Best view in Ft. Walton Beach/Destin

2 Bedroom Condo on the Beach at Okaloosa Island

Waterfront 1-Bdr Private Balcony

Relaxing Gulf Front Couple's Retreat*Beach Service
Other vacation rentals with a pool

Located on the Water | Near Destin | Downtown FWB

Spacious 2BR Oceanfront | Balcony | Pool | Hot Tub

9 Unit Building, Private Pool, Gulf Front View

Luxury Beach Front Condo! 3bd/3ba-Waterscape(A301)

B210 Pirates Plunder

Destin West Villa PH04~ Hot Tub,on Rooftop Terrace

Gulf Dunes 401 - Ocean Eyes

Gorgeous Views & Pristine Pool! Walk to downtown!
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$32,197 GYD | G$34,497 GYD | G$45,368 GYD | G$47,041 GYD | G$48,086 GYD | G$59,585 GYD | G$63,766 GYD | G$44,950 GYD | G$39,723 GYD | G$40,351 GYD | G$33,033 GYD | G$31,779 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$8,363 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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- Rentals with pools United States
- 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
- Gulfarium Marine Adventure Park
- The Track - Destin
- Camp Helen State Park
- Gulf Breeze Zoo
- Shipwreck Island Waterpark
- Gulf World Marine Park
- Henderson Beach State Park
- Point Washington State Forest
- Pensacola Museum of Art
- Destiny East
- Pensacola Bay Center




