Anna Maria Island and Bradenton Area Vacation Rentals By Owner
Welcome to the Anna Maria Island - Bradenton - Gulf Islands area, where pristine beaches and coastal charm invite you to unwind! Discover a variety of vacation rentals, from beachfront cottages to luxurious homes, and start your perfect beachside escape. From Anna Maria, Longboat Key and Bradenton areas start your search below!
Featured
Featured
SeaDuction of Anna Maria Island - 100% up & running after hurricanes!
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Featured
Featured
Anna Maria Island -walk to the beach!
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Beautiful Classy Gulf Coast Anna Maria Island, Private Pool, Close to Beach
Holmes Beach Vacation Rentals
3/BR
2/BA
SLEEPS 6
CREEKSIDE PALMS: 4 mi. to ANNA MARIA ISLAND, Sleeps 14, Heated Pool, Fishing, Kayak and Beach Gear!
Bradenton Vacation Rentals
4/BR
3/BA
SLEEPS 14
New! Waterfront Views w/Private Heated Pool/Spa & Luxury Resort Amenities Sleeps 16
Anna Maria Vacation Rentals
6/BR
4/BA
SLEEPS 16
Alecassandra Vacation Villas - From $300 Family Reunion Location, Villa 4 & 5, 4BR, 4BA, Sleeps 12
Bradenton Beach Vacation Rentals
4/BR
4/BA
SLEEPS 12
Highlighted
Sirenia Beach House - We're Open! - Backyard Beach Waterfront Dock Pool Spa Putting Green Tiki Hut Walk to Beaches
Anna Maria Vacation Rentals
4/BR
3/BA
SLEEPS 10
Highlighted
Sirenia By The Sea - Renovated - 5/5 Waterfront Dock Pool Hot Tub Putting Green - Steps to the Beach
Anna Maria Vacation Rentals
5/BR
5/BA
SLEEPS 12
Large Heated Pool, 2 Master-Bedroom suites, Very Close to Gulf Beach
Anna Maria Vacation Rentals
4/BR
3.5/BA
SLEEPS 8
The Peachy Beach House, Steps to an Anna Maria Beach
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 5
Highlighted
Sirenia Cove - Htd Pool Hot Tub Waterfront Dock Ping Pong Outdoor Bar Backyard Beach Walk to Beaches
Anna Maria Vacation Rentals
4/BR
3/BA
SLEEPS 12
Anna Maria Island- less than 2 min walk to beach!
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Elevator! Spacious Luxury Home Heated Pool & Spa. 3 min walk to Beach!! 3-7 nt stays
Bradenton Beach Vacation Rentals
5/BR
5/BA
SLEEPS 12
PRIME LOCATION ON AMI ** DIRECTLY ON WHITE SUGAR SAND BEACH ** HEATED POOL
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 4
Anna Maria Island Steps to Beach | Pool & Hot Tub | 3BR, 2BA & Balcony
Bradenton Beach Vacation Rentals
3/BR
2/BA
SLEEPS 7
PUTTING GREEN. DISC GOLF. SHUFFLEBOARD. HTD POOL. KIDS THEMED BUNK ROOM. CHAIR LIFT
Bradenton Vacation Rentals
5/BR
2.5/BA
SLEEPS 14
Highlighted
Steps To The Beach, Private & Heated Pool, Renovated - Now Booking Summer/Fall!
Holmes Beach Vacation Rentals
3/BR
1/BA
SLEEPS 6
Americana AMI Lighthouse 3BR w/pool + rooftop deck
Holmes Beach Vacation Rentals
3/BR
2.5/BA
SLEEPS 6
Family vacation on AMI w/pool 4BR, 2.5BA, 8 guests
Holmes Beach Vacation Rentals
4/BR
2.5/BA
SLEEPS 8
Absolute Paradise AMI-Private Beach Access-Water Views From Every Window-Heated Pool- Walk To 14 Restaurants
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 5
Absolute Anna Maria-Private Beach Access-Heated Pool-Water Views From Every Room
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 5
BEAUTIFUL BEACH FRONT CONDO VERY REASONABLY PRICED!!!
Holmes Beach Vacation Rentals
3/BR
2/BA
SLEEPS 6
EDGE OF PARADISE MARGARITAVILLE LUXURY CONDO LOCATED AT THE GATEWAY TO ANNA MARIA ISLAND- TWO MASTER BEDROOMS
One Particular Harbour - Margaritaville Vacation Rentals
3/BR
3/BA
SLEEPS 7
Paradise Awaits by Coastal Chic Vacations
One Particular Harbour - Margaritaville Vacation Rentals
2/BR
2/BA
SLEEPS 5
Beach Daze by Coastal Chic Vacations
One Particular Harbour - Margaritaville Vacation Rentals
2/BR
2/BA
SLEEPS 5
Salty Anchor by Coastal Chic Vacations
One Particular Harbour - Margaritaville Vacation Rentals
2/BR
2/BA
SLEEPS 5
Salty Dogs Beach House on Anna Maria Island. Three bedrooms & baths. Private Pool.
Holmes Beach Vacation Rentals
3/BR
2.5/BA
SLEEPS 6
Entire Duplex W/2 Golf Carts and Pool on Anna Maria Island
Bradenton Beach Vacation Rentals
5/BR
3.5/BA
SLEEPS 12
Bean Point Charmer! 3 Bedrooms Tropical Pool with Outdoor Loungers - Anna Maria Vacation Rental
Anna Maria Vacation Rentals
3/BR
2/BA
SLEEPS 8
Latitude Adjustment Penthouse by Coastal Chic Vacations
One Particular Harbour - Margaritaville Vacation Rentals
3/BR
3/BA
SLEEPS 7
Canal Front! Bring or rent a boat, close to IMG/AMI
Bradenton Vacation Rentals
3/BR
2/BA
SLEEPS 8
SANDY PANTS - Designer Beach Chic Home, Steps to Beach, Backyard Oasis w/ Heated Pool
Holmes Beach Vacation Rentals
3/BR
2.5/BA
SLEEPS 6
Paradise on the Bay by Coastal Chic Vacations
One Particular Harbour - Margaritaville Vacation Rentals
3/BR
3/BA
SLEEPS 7
Beach Escape: Your Ideal Island Retreat!
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Comforts of Home in Secure Gated Community Over Bridge from AMI Now Available Feb 17 2025!
Anna Maria Vacation Rentals
2/BR
2/BA
SLEEPS 6
Seas the Day by Coastal Chic Vacations
One Particular Harbour - Margaritaville Vacation Rentals
2/BR
2/BA
SLEEPS 5
Sol y Mar - Anna Maria Vacation Rental
Holmes Beach Vacation Rentals
3/BR
3.5/BA
SLEEPS 6
cabAnna Maria Beach Block 4 bedroom4.5 Bathroom Private PoolSpa
Anna Maria Vacation Rentals
4/BR
4.5/BA
SLEEPS 8
Coastal Bliss Penthouse by Coastal Chic Vacations
One Particular Harbour - Margaritaville Vacation Rentals
3/BR
3/BA
SLEEPS 7
Swaying Palms by Coastal Chic Vacations
One Particular Harbour - Margaritaville Vacation Rentals
3/BR
3/BA
SLEEPS 6
Sunset Seacret by Coastal Chic Vacations
One Particular Harbour - Margaritaville Vacation Rentals
3/BR
3/BA
SLEEPS 7
Anna Maria Island - just steps to the beach (and pool and tennis court!!!)
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 4
Private Beach Access w/Pool and Tennis!
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Bradenton Beach Club Bliss-3 Bedroom-2 Bathroom Condo-2 Pools-HotTub-Private Beach Access
Bradenton Beach Vacation Rentals
3/BR
2/BA
SLEEPS 6
TROPICAL SUNSET 1 - Anna Maria Island Condo Vacation Rentals
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Spacious condo, steps to beach; no streets to cross. Heated pool.
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
ISLAND HAVEN - Private Beach House with Htd Pool - Anna Maria Island Vacation Rentals
Holmes Beach Vacation Rentals
4/BR
3/BA
SLEEPS 8
BERMUDA BAY CLUB 1467 - Fisherman's Delight Across street from Gulf Beach on Anna Maria Sound
Bradenton Beach Vacation Rentals
3/BR
2.5/BA
SLEEPS 6
BLUE LAGOON SOUTH - North Shore Duplex Heated Pool Close to Beach - Anna Maria Island Rentals
Anna Maria Vacation Rentals
2/BR
2/BA
SLEEPS 6
BLUE LAGOON - 4 Bed 4 bath Duplex Anna Maria Island Vacation Rental with Heated Pool
Anna Maria Vacation Rentals
4/BR
4/BA
SLEEPS 12
SUNSET LANDINGS UNIT 5 - 2 Bedroom Anna Maria Island Vacation Rental
Bradenton Beach Vacation Rentals
2/BR
2.5/BA
SLEEPS 5
Manatee Watch: Beautiful Waterfront Home, Hot Tub, 3 Min Walk to Beach!
Holmes Beach Vacation Rentals
3/BR
2/BA
SLEEPS 6
CASA BONITA - Beach House with Heated Pool Fooseball Outdoor Bar and More - Anna Maria Island Vacation Rental
Bradenton Beach Vacation Rentals
3/BR
2/BA
SLEEPS 8
SEAGRASS FLATS UNIT 2 - 2 Bedroom 2 Bathroom Condo 75 steps to Beach - Anna Maria Island Vacation Rental
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
TROPICAL SUNSET 2 - Anna Maria Island Vacation Rentals
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
SUNSET AZUL - 2 Bedroom Anna Maria Island Vacation Rentals
Holmes Beach Vacation Rentals
2/BR
1/BA
SLEEPS 6
ISLAND RETREAT - Affordable 1 Bedroom Condo - Anna Maria Island Vacation Rentals
Holmes Beach Vacation Rentals
1/BR
1/BA
SLEEPS 4
BEACHSIDE OASIS AT RUNAWAY BAY 229 - Pool Shuffleboard Tennis Steps to Beach - Anna Maria Island Rental
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
FLIP FLOPS FOREVER - Beach House with Heated Pool and Putting Green - Anna Maria Island Rentals
Holmes Beach Vacation Rentals
5/BR
3/BA
SLEEPS 10
Bella Luna at Anna Maria Island Club 46
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 4
PELICAN COVE 3 - Hot Tub Pool Tennis Dock - Steps to Beach - Anna Maria Island Condo Rental
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 5
BRADENTON BEACH CLUB 225 - Gulf to Bay Condo Rental 1/2 block to Beaches - Anna Maria Island Vacation Rental
Bradenton Beach Vacation Rentals
3/BR
2.5/BA
SLEEPS 8
RUM DOG - Ground Floor Bungalow - Affordable Anna Maria Island Vacation Rental
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Sea Life Retreat Vacation Rental on Anna Maria Island at Runaway Bay
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
SEA LIFE AT RUNAWAY BAY 211 - Tennis Shuffleboard Pool 1/2 Block to Beach - Anna Maria Island Rentals
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
ANCHOR SPLASH - 4 Bedroom Hot Tub Heated Pool Historic Cottage - Anna Maria Island Rental
Anna Maria Vacation Rentals
4/BR
2.5/BA
SLEEPS 10
MANATEE LOOKOUT - 3 Bed Beach House with Private Heated Pool - Anna Maria Island Vacation Rentals
Anna Maria Vacation Rentals
3/BR
3/BA
SLEEPS 8
MANNA-TEE BEACH HOUSE - Anna Maria Island Vacation Rental with Pool
Holmes Beach Vacation Rentals
3/BR
2.5/BA
SLEEPS 6
SHOREWALK UNIT 202 - Coastal Condo with Great Amenities Pool, Tennis and More!
Bradenton Vacation Rentals
2/BR
2/BA
SLEEPS 4
SUN PLAZA WEST - 214 - 2 Bedroom Condo - Minimum 2 Week Stays - Anna Maria Island Vacation Rental
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 5
SUNSET LANDINGS UNIT 4 - Anna Maria Island Vacation Rentals
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 5
SUMMER BREEZE Beach House with Private Pool - Anna Maria Island Vacation Rentals
Holmes Beach Vacation Rentals
4/BR
3.5/BA
SLEEPS 8
SWEET FREEDOM AT RUNAWAY BAY 237 - Pool Tennis Shuffleboard - Anna Maria Island Rentals
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
The View at Bradenton Beach Club
Bradenton Beach Vacation Rentals
3/BR
2/BA
SLEEPS 6
BAHAMA MAMA - 3 Bedroom Key West Beach House with Heated Pool and Hot Tub - Anna Maria Island
Holmes Beach Vacation Rentals
3/BR
2/BA
SLEEPS 6
Stoneybrook 2 Bed - 2 Bath Condo with Golf Course View - Seasonal Rental Min 3 Months
Bradenton Vacation Rentals
2/BR
2/BA
SLEEPS 5
GOING COASTAL - 2 Bed 2 Bath Private Beach House with Heated Pool - Anna Maria Island Vacation Rentals
Anna Maria Vacation Rentals
2/BR
2/BA
SLEEPS 6
BAY BLISS AT RUNAWAY BAY 285 - 2 Bedroom 2 Bath - Tennis Shuffleboard and Steps to Beach
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
PELICAN COVE 16 - Tennis Hot Tub Pool Dock - Steps to Beaches - Anna Maria Island Condo Rentals
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 4
SUMMER RETREAT - Quiet Beach House with Private Pool and Hot Tub - Anna Maria Island Vacation Rental
Bradenton Beach Vacation Rentals
4/BR
4.5/BA
SLEEPS 12
Areca Cove On Beautiful Anna Maria Island! 3 Min Walk To Beach!
Holmes Beach Vacation Rentals
4/BR
3.5/BA
SLEEPS 8
AQUA BLU AT ANNA MARIA ISLAND CLUB 27 - Beachfront 2 Bedroom Condo Vacation Rental Hot Tub and Pool!
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 4
MISTY BEACH - Pet Friendly Bungalow Steps to Beaches - Anna Maria Island Vacation Rentals
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
PORTSIDE PARADISE - 4 Bedroom Beach House with Pool and Hot Tub - Anna Maria Island Rentals
Holmes Beach Vacation Rentals
4/BR
6.5/BA
SLEEPS 8
ISLAND DREAM - Beach House with Private Pool and Hot Tub - Anna Maria Island Vacation Rentals
Holmes Beach Vacation Rentals
3/BR
2/BA
SLEEPS 6
SUNSET LANDINGS UNIT 2 - 2 Bedroom Anna Maria Island Vacation Rentals
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 5
SEAGLASS COTTAGE - Bungalow Ground Floor - Anna Maria Island Vacation Rentals
Anna Maria Vacation Rentals
3/BR
2/BA
SLEEPS 6
NO REGRETS! Bright luxury home. Minimum rental 28 days Quick walk to beach and bay.
Longboat Key Vacation Rentals
4/BR
2.5/BA
SLEEPS 8
Sandy Turtle - Pool and Steps to the Beach - Anna Maria Island 3 Bedroom Beachfront Condo Rental
Holmes Beach Vacation Rentals
3/BR
2/BA
SLEEPS 6
STARFISH HAVEN AT RUNAWAY BAY 201 - 2 Bed 2 Bath Anna Maria Island Condo Rental
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Run to the Sun at Runaway Bay 287
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
COCONUT COVE - Luxury Heated Pool Hot Tub Cabana Games - Anna Maria Island Vacation Rental
Anna Maria Vacation Rentals
3/BR
3/BA
SLEEPS 8
SALTY SHAMROCK - Anna Maria Island 4 Bedroom Beach House Vacation Rental with Pool & Hot Tub
Holmes Beach Vacation Rentals
4/BR
2/BA
SLEEPS 8
CASA DEL MAR 4 Bedroom Vacation Rental with Dock - Boat Friendly on Anna Maria Island!
Holmes Beach Vacation Rentals
4/BR
2.5/BA
SLEEPS 8
ANNA MARIA ISLAND CLUB UNIT 22 - Beachfront 2 Bedroom Condo for Rent with Heated Pool
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 4
BLUE LAGOON NORTH - North Shore Duplex with Heated Pool Close to Beaches - Anna Maria Island Rentals
Anna Maria Vacation Rentals
2/BR
2/BA
SLEEPS 6
Perfect Anna Maria Island Location, GROUND FLOOR UNIT, Runaway Bay Condo135
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
A Lazy River Day & Night 4 Bedroom Island Pool Home, Bikes, Beach & Baby Equipment!
Holmes Beach Vacation Rentals
4/BR
3.5/BA
SLEEPS 8
SUNSET TERRACE 204 - 2 bedroom condo - Anna Maria Island Vacation Rentals
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
SEAGRASS FLATS UNIT 1 - 2 Bedroom 2 Bathroom Condo 75 Steps to Beach - Anna Maria Island Vacation Rental
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
THE COZZI COTTAGE - Historic 1 Bed 1 Bath Cottage - Anna Maria Island Vacation Rentals
Holmes Beach Vacation Rentals
1/BR
1/BA
SLEEPS 4
Beautiful 2bedroom 2bathrooms First Floor Condo Super Close To Beach
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
The Oasis at Palmetto - A Luxurious 4-Bedroom Retreat Steps from the Gulf of Mexico with a Private Heated Pool and Spa on Anna Maria Island
Anna Maria Island Vacation Rentals
4/BR
3.5/BA
SLEEPS 8
BATEMAN'S - Luxury Canal Front Home with Pool, Spa, Dock, Close to Bean Point & Pine Ave
Anna Maria Vacation Rentals
4/BR
4/BA
SLEEPS 8
H2O Bungalow by Beach Boutique Rentals
Anna Maria Vacation Rentals
3/BR
3/BA
SLEEPS 8
Beachy Blue by Beach Boutique Rentals
Holmes Beach Vacation Rentals
4/BR
4/BA
SLEEPS 8
Casa Gucci - Anna Maria Island Vacation Rental
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Entire House • 2 Condos • Walk to Beach • Heated Pool • Elevators • Roof Top
Bradenton Beach Vacation Rentals
6/BR
3/BA
SLEEPS 14
Barefoot Bliss by Beach Boutique Rentals
Holmes Beach Vacation Rentals
3/BR
3/BA
SLEEPS 6
Seaside Sunset- Waterfront 2/2 plus bunk room and private dock, 3 blocks to award winning beaches
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Cocktails and Dreams by Beach Boutique Rentals
Holmes Beach Vacation Rentals
4/BR
4/BA
SLEEPS 8
Sea La Vie - Luxurious Anna Maria Island Home with Rooftop Deck, Pool, Spa, and Waterfall – Steps from the Beach!
Anna Maria Island Vacation Rentals
3/BR
3.5/BA
SLEEPS 8
Wish Upon a Starfish by Beach Boutique Rentals
Holmes Beach Vacation Rentals
3/BR
3/BA
SLEEPS 6
Stay 4 nights for additional discounts in February! 8 min to Beach/IMG
Bradenton Vacation Rentals
4/BR
2.5/BA
SLEEPS 12
Canalfront Caribbean Retreat with Pool and Boat Dock
Bradenton Vacation Rentals
3/BR
2/BA
SLEEPS 6
Out of Office by Beach Boutique Rentals
Holmes Beach Vacation Rentals
3/BR
2.5/BA
SLEEPS 6
My Mistress by Beach Boutique Rentals
Anna Maria Vacation Rentals
3/BR
3/BA
SLEEPS 8
Groovy Guava by Beach Boutique Rentals
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 5
Manatee Manor by Beach Boutique Rentals
Holmes Beach Vacation Rentals
3/BR
2/BA
SLEEPS 8
Idyll Tides by Beach Boutique Rentals
Anna Maria Vacation Rentals
3/BR
2/BA
SLEEPS 8
Found Your Sol Mate! Gorgeous Home w/ Pool, Spa, Steps to Bean Point, Dogs OK!
Anna Maria Vacation Rentals
3/BR
2/BA
SLEEPS 8
She's Always Right - Holmes Beach Home w Pool & Spa, 1 Block to Beach & Shops
Holmes Beach Vacation Rentals
4/BR
4/BA
SLEEPS 8
Beachplace 7 – 202 by FGC - Longboat Key Monthly Beachfront Rental
Longboat Key Vacation Rentals
2/BR
2/BA
SLEEPS 4
Paradise Blu by Beach Boutique Rentals
Anna Maria Vacation Rentals
4/BR
4.5/BA
SLEEPS 8
Anna Margaritas by Beach Boutique Rentals
Anna Maria Vacation Rentals
3/BR
2/BA
SLEEPS 6
Mermaid's Crossing 4 bed, 3 bath heated pool and spa
Holmes Beach Vacation Rentals
4/BR
3/BA
SLEEPS 10
Luxury 3 Bed South Facing Villa- central to lake..
Bradenton Vacation Rentals
3/BR
2/BA
SLEEPS 6
Key Lime Cottage by Beach Boutique Rentals
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Esplanade at Lakewood Ranch Monthly Stays
Lakewood Ranch Vacation Rentals
2/BR
2/BA
SLEEPS 4
AcquaLuxe - Exquisite 2022 Lux Canal Home w/ Outdoor Oasis Pool, Spa, Dock, SUP, Kayaks, Fire Pit
Anna Maria Vacation Rentals
4/BR
4/BA
SLEEPS 8
Anna Maria Island SANDY POINT 109 - Walk to beach, shops & restaurants, heated pool, private lanai
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
White Palms by Beach Boutique Rentals
Holmes Beach Vacation Rentals
3/BR
2/BA
SLEEPS 6
LOCATION LOCATION LOCATION large home only 2 houses away from the gulf
Holmes Beach Vacation Rentals
4/BR
3/BA
SLEEPS 8
Casa Mariposa - Luxury Butterfly Garden, Steps to Pine Ave, Pool/Spa, Bikes, 4 Houses to Beach
Anna Maria Vacation Rentals
4/BR
4/BA
SLEEPS 8
SUNSETS ON CARISSA - GORGEOUS ISLAND HOME! 3 Bedroom Block to Beach w Pool
Holmes Beach Vacation Rentals
3/BR
2/BA
SLEEPS 6
Cool Breeze by Beach Boutique Rentals
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Kiwi Cabana by Beach Boutique Rentals
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Whispering Winds by Beach Boutique Rentals
Anna Maria Vacation Rentals
2/BR
2/BA
SLEEPS 6
Sunrise & Sunset Views - Holmes Beach Monthly Vacation Rental
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Island Girl West - Heated Pool, Covered Porches, Beach Gear, Walk to Beach!
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Affordable Rates on Anna Maria Island - Monthly!
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 4
Starfish Paradise by Beach Boutique Rentals
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Anna Maria Beach Place Unit 1 - Downstairs Corner Unit. Steps to The Beach!
Holmes Beach Vacation Rentals
2/BR
1/BA
SLEEPS 4
Jacaranda Gem by Beach Boutique Rentals
Anna Maria Vacation Rentals
3/BR
2.5/BA
SLEEPS 8
A Villa Paradise by Beach Boutique Rentals
Holmes Beach Vacation Rentals
3/BR
2/BA
SLEEPS 6
Tradewinds Resort Cottage Rental - 1 bedroom-sleeps 4 -pet friendly-Welcome to Paradise!
Bradenton Beach Vacation Rentals
1/BR
1/BA
SLEEPS 4
Pier to Pier Paradise by Beach Boutique Rentals
Anna Maria Vacation Rentals
4/BR
4.5/BA
SLEEPS 8
Seaswept Mermaid - This home sustained storm damage and is currently undergoing necessary assessments and preparations, with availability for guests anticipated in 2025.
Anna Maria Vacation Rentals
4/BR
3/BA
SLEEPS 8
Manatee Sanctuary - heated pool & spa; on the canal
Anna Maria Island Vacation Rentals
3/BR
2/BA
SLEEPS 6
GORGEOUS AMI VILLA- STEPS TO THE BEACH, PRIVATE WATERFALL POOL, 3 PATIOS INCLUDING A ROOFTOP PATIO WITH A SWING
Holmes Beach Vacation Rentals
3/BR
3/BA
SLEEPS 8
Our Happy Place on Anna Maria Island
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Paradise Found 6 bed 6.5 bath Heated Pool & Hot TUB Bikes Free Wifi
Holmes Beach Vacation Rentals
6/BR
6.5/BA
SLEEPS 14
PARADISE BEACH HOUSE 6BDs 6.5 bath Block to Beach Private HEATED Pool & Spa, Free WiFi
Holmes Beach Vacation Rentals
6/BR
6.5/BA
SLEEPS 12
Esplanade Resort Community - Ground Level
Lakewood Ranch Vacation Rentals
2/BR
2/BA
SLEEPS 4
Beach front Luxury condo gulf views and gated parking
Holmes Beach Vacation Rentals
3/BR
3/BA
SLEEPS 6
DECKED OUT - Stunning Luxury Home! Huge Sunny Private Pool, Block to Pine 8 Min Walk to Beach
Anna Maria Vacation Rentals
2/BR
2/BA
SLEEPS 4
Highlighted
LAKEWOOD NATIONAL GOLF CLUB 1ST FLOOR 2 BEDROOM 2 BATH PLUS DEN/OFFICE w/ SLEEPER SOFA
Lakewood Ranch Vacation Rentals
2/BR
2/BA
SLEEPS 6
#174 Runaway Bay or better known as Paradise! Our home away from home.
Bradenton Beach Vacation Rentals
2/BR
2/BA
SLEEPS 5
No Tan Lines by Beach Boutique Rentals
Anna Maria Vacation Rentals
4/BR
4/BA
SLEEPS 8
Mariner's Crossing - Stunning Luxury Home w/ Gulf Views From Every Room, Rooftop Deck, & Pool/Spa
Holmes Beach Vacation Rentals
8/BR
7.5/BA
SLEEPS 18
SUNSET MARGARITA - Luxury Condo, Pool, Bikes, Just 5 Mins to Anna Maria Gulf Beaches!
One Particular Harbour - Margaritaville Vacation Rentals
2/BR
2/BA
SLEEPS 5
The Happy Hibiscus Island Oasis with Ocean Views
Anna Maria Vacation Rentals
4/BR
2/BA
SLEEPS 8
Vitamin Sea has everything! Heated pool & spa, elevator, rooftop deck, water views +++
Anna Maria Vacation Rentals
5/BR
5/BA
SLEEPS 12
Sunset Villa D by Beach Boutique Rentals
Holmes Beach Vacation Rentals
2/BR
1/BA
SLEEPS 6
THE COTTAGE ON PINE - Adorable Renovated Cottage w/Private Heated Pool, On Main Street of Anna Maria
Anna Maria Vacation Rentals
2/BR
1/BA
SLEEPS 4
Unique beach house near Bean Point, heated pool and just 3 min to beach.
Anna Maria Vacation Rentals
3/BR
2/BA
SLEEPS 6
Manatee Harbour - heated pool, on the canal
Anna Maria Island Vacation Rentals
2/BR
2/BA
SLEEPS 4
NEW LISTING! Longboat Key Monthly Rental - Beachplace 4 -204
Longboat Key Vacation Rentals
2/BR
2/BA
SLEEPS 6
CASA POSADA - So Close to Beach You Hear the Waves! Updated Clean Beach Cottage, Start $180n
Anna Maria Vacation Rentals
2/BR
1/BA
SLEEPS 6
TERN KEY - Pristine Spacious Luxury Canal Home with Pool, Spa, Dock, Bikes, Close to Beach!
Anna Maria Vacation Rentals
4/BR
4.5/BA
SLEEPS 8
Beachfront Longboat Key Seasonal Rental
Longboat Key Vacation Rentals
2/BR
2/BA
SLEEPS 6
Reel Royale a Canal Home on Anna Maria Island
Holmes Beach Vacation Rentals
4/BR
4/BA
SLEEPS 8
AMI PEPPERTREE PARADISE - Cozy Updated Home w/Heated Pool on North End of Island, 2 Houses to Beach!
Anna Maria Vacation Rentals
3/BR
2/BA
SLEEPS 8
Grains of Sand by Beach Boutique Rentals
Holmes Beach Vacation Rentals
4/BR
4.5/BA
SLEEPS 8
Pool House - Bradenton Snowbird Vacation Rental
Bradenton Vacation Rentals
3/BR
2/BA
SLEEPS 9
COZY CABANA EAST - GORGEOUS Renovated w/ Pvt. Pool, Backyard Oasis, Walk to Beach w Beach Gear!
Holmes Beach Vacation Rentals
2/BR
2/BA
SLEEPS 6
Resort-Style Ground Floor 1-Bdr. Suite On Vista Lake, Heated Pool & Spa
Holmes Beach Vacation Rentals
1/BR
2/BA
SLEEPS 2
Starfish Isle 4 Bedroom3 Bath ~ Private HEATED Pool & Spa, Close to BEACH! Free WiFi
Holmes Beach Vacation Rentals
4/BR
3/BA
SLEEPS 4
Salty Pirate - This home sustained storm damage and is currently undergoing necessary assessments and preparations, with availability for guests anticipated in 2025.
Anna Maria Vacation Rentals
4/BR
3/BA
SLEEPS 11
Griffins Island Getaway - Coastal Luxury with Private Heated Pool, Game Room, and Just Minutes from Anna Maria Island's Beaches!
Holmes Beach Vacation Rentals
3/BR
2/BA
SLEEPS 6
Sunshine Cottage Anna Maria Island - Waterfront Pool Home with Boat Dock! New Construction and open post-hurricanes!!
Anna Maria Vacation Rentals
3/BR
2/BA
SLEEPS 10
POINT'S HIDEAWAY - Beautiful Island Home w/ Rooftop Water Views on Bean Point! Pool, Bar, Foosball!
Anna Maria Vacation Rentals
3/BR
3/BA
SLEEPS 8
Gone Coastal 3 by Beach Boutique Rentals
Anna Maria Vacation Rentals
3/BR
2.5/BA
SLEEPS 6
Crosswind Cottages - Sprawling 3 bed 2.5 bath heated pool elevator FREE WIFI Sleeps 9
Holmes Beach Vacation Rentals
3/BR
2.5/BA
SLEEPS 9