Vacation Rentals in Watersound, Florida

50 Properties Available

Beach Escape w/ Pool, Cart and Game Room Private vacation home
Beach Escape w/ Pool, Cart and Game Room
$3433 / night
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Beachfront Home with Private, Heated Pool Private vacation home
Beachfront Home with Private, Heated Pool
$1892 / night
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Summer Availability! Gulf Views! Steps From The Beach! Large Outdoor Living Space! Private vacation home
Summer Availability! Gulf Views! Steps From The Beach! Large Outdoor Living Space!
$1586 / night
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Watersound Waves B108-Sleeps 6-Gulf Views Private vacation home
Watersound Waves B108-Sleeps 6-Gulf Views
$1552 / night
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Luxe Watersound Retreat with Private Pool Private vacation home
Luxe Watersound Retreat with Private Pool
$1484 / night
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Beach Bear Cottage - Watersound, Gulf Views, Private Pool, Bikes, & Golf Cart Private vacation home
Beach Bear Cottage - Watersound, Gulf Views, Private Pool, Bikes, & Golf Cart
$1377 / night
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Prominence on 30A - Elite Escape - Pet Friendly, Golf Cart & Bikes Incl, 2 Pools Private vacation home
Prominence on 30A - Elite Escape - Pet Friendly, Golf Cart & Bikes Incl, 2 Pools
$1361 / night
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Elegant Getaway with Pool and Golf Cart Private vacation home
Elegant Getaway with Pool and Golf Cart
$1302 / night
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8 Bedrooms w\/ Private Heated Pool optional Golf Cart Included, Sleeps 16 Private vacation home
8 Bedrooms w\/ Private Heated Pool optional Golf Cart Included, Sleeps 16
$1185 / night
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Beach Access and Private Saltwater Pool Private vacation home
Beach Access and Private Saltwater Pool
$1105 / night
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Beach Escape with Carriage, Near Pool Private vacation home
Beach Escape with Carriage, Near Pool
$1067 / night
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PANORAMIC GULF FRONT in WATERSOUND BRIDGES! TOTAL RENOVATION!! Condo
PANORAMIC GULF FRONT in WATERSOUND BRIDGES! TOTAL RENOVATION!!
$1050 / night
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Prominence 30Ashack - Pet Friendly, Pools, The Big Chill, Free Bikes & More! Private vacation home
Prominence 30Ashack - Pet Friendly, Pools, The Big Chill, Free Bikes & More!
$956 / night
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Perfect fall beach getaway - Sunsets, heated pool, private beach and fireplaces! Private vacation home
Perfect fall beach getaway - Sunsets, heated pool, private beach and fireplaces!
$952 / night
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Prominence 30A Just Beachy - Golf Cart, 2 Pools, 4 Bikes, Big Chill, Free Golf Private vacation home
Prominence 30A Just Beachy - Golf Cart, 2 Pools, 4 Bikes, Big Chill, Free Golf
$937 / night
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Prominence 30A Seas the Day - Pet Friendly, Golf Cart, 4 Bikes, 2 Pools, Beach Private vacation home
Prominence 30A Seas the Day - Pet Friendly, Golf Cart, 4 Bikes, 2 Pools, Beach
$915 / night
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4 Seater Golf Cart. 2 Blocks to Pool & Beach Access! Gourmet Kitchen! Private vacation home
4 Seater Golf Cart. 2 Blocks to Pool & Beach Access! Gourmet Kitchen!
$805 / night
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Gulf-Front 3BR condo in WaterSound Beach, Steps to Beach & Pool Condo
Gulf-Front 3BR condo in WaterSound Beach, Steps to Beach & Pool
$737 / night
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Prominence on 30A Rays for Days - Golf Cart, Pet Friendly, 2 Pools, 4 Bikes Incl Private vacation home
Prominence on 30A Rays for Days - Golf Cart, Pet Friendly, 2 Pools, 4 Bikes Incl
$633 / night
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BEAUTIFUL VIEWS! WATERSOUND-Beachfront, Views from All Rooms, 3 Bdrms, Slps 8 Condo
BEAUTIFUL VIEWS! WATERSOUND-Beachfront, Views from All Rooms, 3 Bdrms, Slps 8
$610 / night
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Family-Friendly WaterSound Escape Condo
Family-Friendly WaterSound Escape
$584 / night
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Stay Anchored 30A | 6-Seat LSV + Heated Pool Private vacation home
Stay Anchored 30A | 6-Seat LSV + Heated Pool
$572 / night
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Mint Julep - 3BR/2.5BA Prominence Home - Sleeps 9 - 6-Passenger LSV Condo
Mint Julep - 3BR/2.5BA Prominence Home - Sleeps 9 - 6-Passenger LSV
$563 / night
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Prominence 30A - Lazy Daze - 2 Pools, Golf Cart and 4 Bikes Incl! Beach Nearby Private vacation home
Prominence 30A - Lazy Daze - 2 Pools, Golf Cart and 4 Bikes Incl! Beach Nearby
$557 / night
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Pet Friendly, Golf Cart and 4 Bikes Included, 2 Pools, Beach Book 2025 Today Private vacation home
Pet Friendly, Golf Cart and 4 Bikes Included, 2 Pools, Beach Book 2025 Today
$542 / night
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Prominence - Joy Found, 30A - Beach, 2 Pools - Golf Cart, 4 Bikes, Fall Sale Private vacation home
Prominence - Joy Found, 30A - Beach, 2 Pools - Golf Cart, 4 Bikes, Fall Sale
$530 / night
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30A BIG EASY Private vacation home
30A BIG EASY
$488 / night
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Prominence 30A Golf Cart, 4 Bikes, Beach, 2 Pools - Free Golf, The Big Chill Private vacation home
Prominence 30A Golf Cart, 4 Bikes, Beach, 2 Pools - Free Golf, The Big Chill
$478 / night
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Mobile - Newly renovated Seacrest Beach townhome steps to the beach, 2 bikes! Private vacation home
Mobile - Newly renovated Seacrest Beach townhome steps to the beach, 2 bikes!
$475 / night
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Beach, 2 Pools, Pet Friendly, Golf Cart, 4 Bikes,  Free round of Golf Daily Incl Private vacation home
Beach, 2 Pools, Pet Friendly, Golf Cart, 4 Bikes, Free round of Golf Daily Incl
$467 / night
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Prominence 30A Pet Friendly, 6 Seater Golf Cart, 4 Bikes, Beach, 2 Pools and Fun Private vacation home
Prominence 30A Pet Friendly, 6 Seater Golf Cart, 4 Bikes, Beach, 2 Pools and Fun
$464 / night
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Surfer's Retreat: 2 Golf Carts, Bikes, Pool! Private vacation home
Surfer's Retreat: 2 Golf Carts, Bikes, Pool!
$458 / night
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Prominence - Beach, 2 Pools - 30A Golf Cart, 4 Bikes Incl - Free Golf Private vacation home
Prominence - Beach, 2 Pools - 30A Golf Cart, 4 Bikes Incl - Free Golf
$443 / night
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Suntans and Sunsets on 30A • 2 BR\/2 BA • Pet Friendly • Golf Cart Private vacation home
Suntans and Sunsets on 30A • 2 BR\/2 BA • Pet Friendly • Golf Cart
$426 / night
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Coastal Cottage with Golf Cart and Bikes Private vacation home
Coastal Cottage with Golf Cart and Bikes
$426 / night
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Ocean Eyes | 30A Rental Next to Pool & The HUB Private vacation home
Ocean Eyes | 30A Rental Next to Pool & The HUB
$404 / night
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Prominence 30A Pet Friendly, Golf Cart, 4 Bikes, Beach, 2 Pools 1 heated season Private vacation home
Prominence 30A Pet Friendly, Golf Cart, 4 Bikes, Beach, 2 Pools 1 heated season
$400 / night
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30A Pet Friendly, Sleeps 10, 4 Bikes, 2 Pools -  Free Round Golf Incl Private vacation home
30A Pet Friendly, Sleeps 10, 4 Bikes, 2 Pools - Free Round Golf Incl
$392 / night
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The Hideaway on 30A | with Golf Cart and 4 Bikes Included Private vacation home
The Hideaway on 30A | with Golf Cart and 4 Bikes Included
$390 / night
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Lucky Beach:A Family Retreat! Pool~Golf Cart~Bikes Private vacation home
Lucky Beach:A Family Retreat! Pool~Golf Cart~Bikes
$378 / night
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\"BIG EASY\" ON 30A Private vacation home
\"BIG EASY\" ON 30A
$376 / night
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PROMINENCE 30A CLOSE TO POOL DIRECTLY ACROSS FROM HUB Private vacation home
PROMINENCE 30A CLOSE TO POOL DIRECTLY ACROSS FROM HUB
$375 / night
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LatitudeAdjustment @ Prominence N. 30A Golf Cart\/4 Bikes\/Bch Equip-Near The HUB Private vacation home
LatitudeAdjustment @ Prominence N. 30A Golf Cart\/4 Bikes\/Bch Equip-Near The HUB
$375 / night
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Gulf Front Condo- Compass Point I, Unit 204 by Royal Destinations Condo
Gulf Front Condo- Compass Point I, Unit 204 by Royal Destinations
$363 / night
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Prominence - Reef Intermission Pet Friendly, 4 Bikes - Beach, 2 Pools, Free Golf Private vacation home
Prominence - Reef Intermission Pet Friendly, 4 Bikes - Beach, 2 Pools, Free Golf
$338 / night
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Prominence Coastal Soul - Golf Cart, 4 Bikes, 2 Pools - Big Chill Private vacation home
Prominence Coastal Soul - Golf Cart, 4 Bikes, 2 Pools - Big Chill
$325 / night
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6 Seater Cart | Great Location | Pool | near beach Private vacation home
6 Seater Cart | Great Location | Pool | near beach
$321 / night
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Prominence 30A Pet Friendly, 4 Bikes Incl, 2 Pools, Beach, The Big Chill and Fun Private vacation home
Prominence 30A Pet Friendly, 4 Bikes Incl, 2 Pools, Beach, The Big Chill and Fun
$321 / night
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Paradise Hide A Way - Prominence 3 BR\/2.5 Bath Condo
Paradise Hide A Way - Prominence 3 BR\/2.5 Bath
$316 / night
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Prominence on 30A - Pet Friendly Pools, Beach, 4 Bikes, Free Golf Daily & More! Private vacation home
Prominence on 30A - Pet Friendly Pools, Beach, 4 Bikes, Free Golf Daily & More!
$304 / night
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