Manatee Area Rentals
From $518 per night (USD)VRBO
Blue Water Escape by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The beautiful Blue Water Escape! Experience its panoramic rooftop deck views with a location in the heart of Bradenton B ...
From $518 per night (USD)VRBO
From $314 per night (USD)Expedia
August Deals • Amazing Location • Private Deck • Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
August Special Savings! Take advantage of discounted August rates and plan one last unforgettable beach getaway before s ...
From $314 per night (USD)Expedia
From $658 per night (USD)VRBO
Do you love the beach?
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Seaside Sanctuary is the ground level unit of a beachfront duplex. It is the 2nd home from the beach with no roads ...
From $658 per night (USD)VRBO
From $1058 per night (USD)Expedia
Aloha Beaches! Newly Renovated 4 Bedroom 3 Bath Home w/ Private Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Aloha Beaches a newly renovated custom beach destination. Kick off your shoes, turn off your phone, don’t win ...
From $1058 per night (USD)Expedia
From $997 per night (USD)VRBO
Dolphin Tales: Pool, Bay Views & Private Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Dolphin Tales by Anna Maria Life Vacation Rentals 836 S Bay Blvd, Anna Maria, FL 34216 What You'll Love About This Home ...
From $997 per night (USD)VRBO
From $259 per night (USD)Expedia
Casa Sierra 203B - 2BR Condo with Pool - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Sierra Resort is a private Mediterranean style four unit complex in Holmes Beach on beautiful Anna Maria Island. Th ...
From $259 per night (USD)Expedia
From $240 per night (USD)VRBO
Sugaree - 2bedroom Private Pool Property in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Anna Maria Island vacation rental offers one king bed, two twin beds and a queen sleeper sofa all covered in premiu ...
From $240 per night (USD)VRBO
From $449 per night (USD)Expedia
Beach Getaway in Bradenton Beach with Games, 2 Mins to Beach! - A Twist of Lime
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
A Twist of Lime by AMI Locals TPL22-000045, CND5105493 Welcome to A Twist of Lime by AMI Locals, a vibrant three bedro ...
From $449 per night (USD)Expedia
From $547 per night (USD)VRBO
Coconuts108 - GULFFRONT - 1BR/1BA with pool - By Island Real Estate Vacations
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconuts Beach Resort 108 is a fully remodeled beachfront condo located directly on the Gulf in Holmes Beach on Anna Mar ...
From $547 per night (USD)VRBO
From $631 per night (USD)Expedia
The Lady Fish by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on the far North end of Anna Maria Island, with the beach cottage is just around the corner, The Lady Fish is a ...
From $631 per night (USD)Expedia
From $430 per night (USD)VRBO
Chapter 2: Renovated pool home, tiki hut and close to beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Chapter 2 Create some magic memories in a slice of “Old Florida”. Relax outside in the heated saltwater p ...
From $430 per night (USD)VRBO
From $594 per night (USD)Expedia
TWO SHELL COVE - BEACHFRONT -Amazing Remodel right on the beach - I
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
TWO SHELL COVE on Anna Maria Island. Right on the beach. Sunsets from your windows and patio Open plan with amazing kit ...
From $594 per night (USD)Expedia
From $472 per night (USD)VRBO
Florida Dream: Rent pure luxury in Bradenton / Anna Maria Iceland
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
TIP: Beautiful pool villa for max. 8 persons, 245 m² living space: 4 bedrooms, 2.5 bathrooms, large living area, ultra m ...
From $472 per night (USD)VRBO
From $454 per night (USD)Expedia
🌴”Kiwi Cottage at Holmes Beach” - Private Heated Pool +Spa+Walk to the Beach! 🌞
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Kiwi Coastal Cottage is under new ownership and every space has been thoughtfully redecorated with a cozy coastal island ...
From $454 per night (USD)Expedia
From $267 per night (USD)VRBO
Beautiful bayfront view! December 2026 dates available now!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Harbour Villa #305 – a beautifully updated bayfront retreat offering the perfect blend of comfort, style, and ...
From $267 per night (USD)VRBO
From $259 per night (USD)Expedia
Runaway Bay 283 by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Runaway Bay 283 is a second-floor unit in this well sought after condo community. Enjoy the sights and sounds of this tr ...
From $259 per night (USD)Expedia
From $834 per night (USD)VRBO
Golf Cart - Coconut Cove by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid ...
From $834 per night (USD)VRBO
From $263 per night (USD)Expedia
Longboat Key with Gulf to Bay access. Beautiful view of Bishop's Bayou.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Outdoor living at its best in this updated WATERFRONT first floor condo in Whitney Beach Bay Side. Mesmerizing views of ...
From $263 per night (USD)Expedia
From $375 per night (USD)VRBO
Breathtaking Beach Front Property Ground Floor Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Granite and stainless steel appliances in the kitchen. The living room’s sliding patio door provides first floor access ...
From $375 per night (USD)VRBO
From $5007 per night (USD)Expedia
Spectacular Sarasota Bay Views from all rooms
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Seasonal Rental. Spectacular views of Sarasota Bay and the Gulf of Mexico from this island penthouse condo. Enjoy the ma ...
From $5007 per night (USD)Expedia
From $806 per night (USD)VRBO
Beachfront 2/1 - Newly Remodeled right on the beach. Amazing Sunsets - D
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
TWO SHELL COVE: Your Dream Beachfront Escape on Anna Maria Island Experience the ultimate beachfront vacation at TWO SHE ...
From $806 per night (USD)VRBO
From $1752 per night (USD)Expedia
Cloud 9 | Beachfront Pool & Spa | Bean Point, Golf Cart
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Summary: Welcome to Cloud 9, a stunning beachfront retreat where modern luxury meets relaxed coastal living. Perfectly ...
From $1752 per night (USD)Expedia
From $1643 per night (USD)VRBO
Big Family Beach House: Large family home, heated pool, putting green
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Big Family Beach House, the name says it all! Coastal elegance describes this spectacular large family home. It's loca ...
From $1643 per night (USD)VRBO
From $528 per night (USD)Expedia
Island Retreat- Stunning 4 bedroom with private heated pool and walk to beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Island Retreat 4805 2nd Avenue, Holmes Beach, FL 34217 VRC16-000621 What you will love about this property: • Private po ...
From $528 per night (USD)Expedia
From $825 per night (USD)VRBO
Blue Water View- 6 bedrooms with amazing rooftop deck and private heated pool
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Blue Water View 118 50th Street, Holmes Beach, FL 34217 VRC16-000296 What you will love about this property: • 4 houses ...
From $825 per night (USD)VRBO
From $1674 per night (USD)Expedia
Serendipity Deux | Luxury Beachfront Pool & Spa | Golf Cart | Elevator
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Escape to Serendipity Deux, a luxurious 4-bedroom house on Anna Maria Island, where refined interiors meet the ...
From $1674 per night (USD)Expedia
From $562 per night (USD)VRBO
Sea Grape Inn #6- Beachfront Property
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
BEACH VIEW Condo- 2nd Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper. ...
From $562 per night (USD)VRBO
From $562 per night (USD)Expedia
Sea Grape Inn #2- Beachfront Property
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
BEACH VIEW Condo- 1st Floor of Beach Front Property, 2 BDRMS/2 BATH, Sleeps 6: 1-King Bed, 2-Twin Beds & 1-Sofa Sleeper, ...
From $562 per night (USD)Expedia
From $634 per night (USD)VRBO
Oceans Blue Walk to the beach, stunning pool/spa private deck great location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Indulge in the ultimate beach escape to “Oceans Blue” located on the *premier corner* of Coconut & Los Cedros in Anna Ma ...
From $634 per night (USD)VRBO
From $1378 per night (USD)Expedia
Amie House BEACH Getaway *GOLF CART ONSITE*
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Amie House on Anna Maria Island. Modern Amie House is perfectly situated a short 4 minute walk to the pri ...
From $1378 per night (USD)Expedia
From $493 per night (USD)VRBO
Bradenton Beach Club 251 - Anna Maria Island - Condo 3 Bedroom/ 2 1/2 Bath, maximum occupancy of 6 people.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bradenton Beach Club 251 - Anna Maria Island - 3 Bedroom/ 2 1/2 Bath, maximum occupancy of 6 people. Distance to the Be ...
From $493 per night (USD)VRBO
From $186 per night (USD)Expedia
Ty's Canal Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A one bedroom efficiency with a quiet cottage setting on a canal. Come watch the boats come up and down the canal and e ...
From $186 per night (USD)Expedia
From $184 per night (USD)VRBO
Private historical completely renovated cottage with 60 ft dock on Sarasota Bay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Gray House is a completely renovated historical cottage dating back to the early 1900s, in the historical fishing vi ...
From $184 per night (USD)VRBO
From $267 per night (USD)VRBO
Beach Palms 8B-Beach 1 Minute Walk, Heated Pool, Free Wi-Fi-Dock-Private Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most ...
From $267 per night (USD)VRBO
From $620 per night (USD)VRBO
Sol Mate – Pet Home w/ Heated Pool, Spa, Walk to Bean Point Beach & Pine Ave
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Sol Mate! On Anna Maria Island (Anna Maria, FL) The Space Your island escape designed for families and frien ...
From $620 per night (USD)VRBO
From $924 per night (USD)Expedia
Canal Front with Boat Dock! Perfect Location! Game Room! -A Pirate's Dream
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A Pirate’s Dream by AMI Locals Welcome to A Pirate’s Dream by AMI Locals, a grand waterfront retreat that perfectly bl ...
From $924 per night (USD)Expedia
From $193 per night (USD)VRBO
Heated Pool, Walk to Beach & Shops- Perfect Location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
You're just steps from the beach when you stay at Villa by the Sea #3! This gem of a condo is all about convenience as i ...
From $193 per night (USD)VRBO
From $466 per night (USD)Expedia
Coquina Moorings 201 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath with Den/3rd room , maximum occupancy of 6 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Coquina Moorings, Unit 201 - Anna Maria Island - 2 Bedroom/ 2 Bath with Den, maximum occupancy of 6 people. Bay and Gul ...
From $466 per night (USD)Expedia
From $322 per night (USD)VRBO
Gulf Watch 111 - Anna Maria Island - Condo 2 Bedroom / 2 Bath Gulf to Bay access, maximum occupancy of 5 people.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Gulf Watch 111 - Anna Maria Island - 2 Bedroom / 2 Bath, maximum occupancy of 5 people. Distance to the Beach: across t ...
From $322 per night (USD)VRBO
From $708 per night (USD)Expedia
Dream Catcher- Key West style beach house on North end.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Live out your dream of a tropical paradise at our Key West style beach house on the North end of Anna Maria. Start your ...
From $708 per night (USD)Expedia
From $486 per night (USD)VRBO
Pelican Cove 1 - Anna Maria Island - Condo 2 Bedroom /2 Bath beach side, maximum occupancy of 6 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Pelican Cove 1- Anna Maria Island - Condo 2 Bedroom /2 Bath, maximum occupancy of 6 people. Gulf View Florida's Finest ...
From $486 per night (USD)VRBO
From $365 per night (USD)Expedia
Pelican Cove 14 - Anna Maria Island - Condo 2 Bedroom /2 Bath bay view, maximum occupancy of 4 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Pelican Cove 14 - Anna Maria Island - Condo 2 Bedroom /2 Bath, maximum occupancy of 4 people. Bay View Florida's Fi ...
From $365 per night (USD)Expedia
From $471 per night (USD)VRBO
Pelican Cove 13 - Anna Maria Island - Condo 2 Bedroom /2 Bath bay view, maximum occupancy of 6 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Pelican Cove 13 - Anna Maria Island - Condo 2 Bedroom /2 Bath, maximum occupancy of 6 people. Bay View Florida's Fin ...
From $471 per night (USD)VRBO
From $367 per night (USD)Expedia
Pelican Cove 4 - Anna Maria Island - Condo 2 Bedroom /2 Bath beach side, maximum occupancy of 5 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
Pelican Cove 4 - Anna Maria Island - Condo 2 Bedroom /2 Bath, maximum occupancy of 5 people. Gulf View Florida's Fin ...
From $367 per night (USD)Expedia
From $293 per night (USD)VRBO
Gulf Watch 205 - Anna Maria Island - Condo 2 Bedroom / 2 Bath Gulf to Bay access, maximum occupancy of 4 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Gulf Watch 205 - Anna Maria Island - 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Distance to the Beach: across t ...
From $293 per night (USD)VRBO
From $1149 per night (USD)Expedia
Beach Side Paradise-Beautiful luxury 6 bedrooms with amazing views, private pool
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Beach Side Paradise 203 17th Street North, Bradenton Beach, FL 34217 What you will love about this property: • Rooftop ...
From $1149 per night (USD)Expedia
From $377 per night (USD)VRBO
Anna Maria Island Club 12 - Condo 2 Bedroom/ 2 Bath beach view, maximum occupancy of 4 people. Community pool, Max 1 vehicle.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Anna Maria Island Club 12 - Anna Maria Island - Condo - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Gulf Fro ...
From $377 per night (USD)VRBO
From $407 per night (USD)Expedia
Coquina Beach Club 103 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath ocean view, maximum occupancy of 6 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Coquina Beach Club, Unit 103 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. Gulf View Condo - ...
From $407 per night (USD)Expedia
From $957 per night (USD)VRBO
Kingfish: *Canalfront *Paddleboards *Putt Putt *Heated Pool *Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
You want WARMTH –You want SUN – You NEED BEACH – KINGFISH is just the thing! Escape to one of Anna Maria Island’s most ...
From $957 per night (USD)VRBO
From $347 per night (USD)Expedia
Gulf Watch 115 - Anna Maria Island - Condo 2 Bedroom / 2 Bath Gulf to Bay access, maximum occupancy of 4 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Gulf Watch 115 - Anna Maria Island - 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Bay Front - Heated Community Po ...
From $347 per night (USD)Expedia
From $365 per night (USD)VRBO
Pelican Cove 11 - Anna Maria Island - Condo 2 Bedroom /2 Bath bay view, maximum occupancy of 4 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Pelican Cove 11 - Anna Maria Island - Condo 2 Bedroom /2 Bath, maximum occupancy of 4 people. Bay View Florida's Fine ...
From $365 per night (USD)VRBO
From $361 per night (USD)Expedia
Pelican Cove 12 - Anna Maria Island - Across the street from the beach- Condo 2 Bedroom /2 Bath bay view with a community pool, maximum occupancy of 6 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Pelican Cove 12 - Anna Maria Island - Condo 2 Bedroom /2 Bath, maximum occupancy of 5 people. Bay View Florida's Fi ...
From $361 per night (USD)Expedia
From $669 per night (USD)VRBO
Anna Maria Island Club 45, Condo 2 Bedroom/ 2 Bath ocean view, maximum occupancy of 4 people. Community pool, Max 1 vehicle.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Anna Maria Island Club 45 - Anna Maria Island - Condo - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Gulf View -We ...
From $669 per night (USD)VRBO
From $882 per night (USD)Expedia
637 Norton - Longboat Key - Private canal home 4 Bedroom/ 3.5 Bath with private pool, maximum occupancy of 8 people.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
637 Norton - Longboat Key - 4 Bedroom/ 3.5 Bath, maximum occupancy of 8 people. Canal Home - Private Pool - Boat Dock - ...
From $882 per night (USD)Expedia
From $812 per night (USD)VRBO
A Ray Of Sunshine- Amazing property private basketball court pool/spa on a canal
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A Ray of Sunshine 232 Chilson Avenue, Anna Maria, FL 34216 What you will love about this property: • Canal front home w ...
From $812 per night (USD)VRBO
From $472 per night (USD)Expedia
Pelican Cove 5 - Anna Maria Island - Condo 2 Bedroom /2 Bath beach side, maximum occupancy of 5 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
Pelican Cove 5 - Anna Maria Island - Condo 2 Bedroom /2 Bath, maximum occupancy of 5 people. Gulf View Florida's Fin ...
From $472 per night (USD)Expedia
From $344 per night (USD)VRBO
Bayview Condo C - Anna Maria Island - Condo 2 Bedroom/ 2 Bath bay view, maximum occupancy of 4 people. Distance to the Beach: 1 block
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Bayview Condo, Unit C - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Community Pool - Bay View ...
From $344 per night (USD)VRBO
From $1269 per night (USD)Expedia
Anapauo Beachhouse: Million dollar views of Tampa Bay!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Anapauo Beachhouse! Pronounced ahn-ap-ow’-o, it is a Greek word meaning to give rest, refresh, recover and co ...
From $1269 per night (USD)Expedia
From $401 per night (USD)VRBO
Coquina Beach Club 202 - Anna Maria Island- Condo 2 Bedroom/ 2 Bath ocean view, maximum occupancy of 6 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Coquina Beach Club 202 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. Gulf View Condo - Commun ...
From $401 per night (USD)VRBO
From $821 per night (USD)Expedia
Bay Beauty: Private Intra-Coastal front home with sprawling views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Bay Beauty, a charming 4-bedroom, 3-bath waterfront retreat in Bradenton Beach where laid-back island living ...
From $821 per night (USD)Expedia
From $397 per night (USD)VRBO
Bradenton Beach Club 230 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 6 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Bradenton Beach Club, Unit 230 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. Distance to the ...
From $397 per night (USD)VRBO
From $765 per night (USD)Expedia
A Time Out: *Quaint Cottage *Heated Pool *Across the street from the Bay!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to "A Time Out" - your perfect retreat in paradise! This charming 4-bedroom, 2-bathroom home invites you to expe ...
From $765 per night (USD)Expedia
From $346 per night (USD)VRBO
Pelican Cove 9 - Anna Maria Island - Condo 2 Bedroom /2 Bath bay side, maximum occupancy of 5 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
Pelican Cove 9 - Anna Maria Island - Condo 2 Bedroom /2 Bath maximum occupancy of 5 people. Bay View. Florida's Fines ...
From $346 per night (USD)VRBO
From $365 per night (USD)Expedia
Bradenton Beach Club 228 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 6 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Bradenton Beach Club, Unit 228 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. Distance to the ...
From $365 per night (USD)Expedia
From $325 per night (USD)VRBO
Gulf Watch 210 - Anna Maria Island - Condo 2 Bedroom / 2 Bath Gulf to Bay access, maximum occupancy of 4 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Gulf Watch 210 - Anna Maria Island - 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Distance to the Beach: across t ...
From $325 per night (USD)VRBO
From $831 per night (USD)Expedia
Lovin' the Sannd: North-end cottage, luxury amenities
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
If you're looking to escape the hustle and bustle of everyday life, look no further than "Lovin' the SANND". This three ...
From $831 per night (USD)Expedia
From $559 per night (USD)VRBO
707 N Bay The Shell House - Anna Maria Island - Private home 3 Bedroom/ 2 1/2 Bath with private pool, maximum occupancy of 6 people.
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 6
707 North Bay Boulevard - The Shell House- 3 Bedroom/ 2 1/2 Bath, maximum occupancy of 6 people. Private Pool - Distanc ...
From $559 per night (USD)VRBO
From $588 per night (USD)Expedia
Wonderful and updated 2 bedroom/2 bath direct beach front. Panoramic views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Direct gulf-front 2BR/2BA condo in a charming 4-unit building on Anna Maria Island. This lower-level gem is up just one ...
From $588 per night (USD)Expedia
From $479 per night (USD)VRBO
Sunset Terrace 203 - Anna Maria Island - Beach front condo 2 Bedroom/ 2 Bath Bradenton Beach, Anna Maria Island, maximum occupancy of 4 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Sunset Terrace 203 - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Gulf Front - Community Pool. ...
From $479 per night (USD)VRBO
From $362 per night (USD)Expedia
Pelican Cove 10 - Anna Maria Island - Condo 2 Bedroom /2 Bath bay view, maximum occupancy of 5 people.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
Pelican Cove 10 - Anna Maria Island - Condo 2 Bedroom /2 Bath, maximum occupancy of 5 people. Bay View Florida's Fines ...
From $362 per night (USD)Expedia
From $376 per night (USD)VRBO
Anna Maria Island Club 26, Condo 2 Bedroom/ 2 Bath ocean view, maximum occupancy of 4 people. Community pool, Max 1 vehicle.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Anna Maria Island Club 26 - Anna Maria Island - Condo - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Gulf Front - ...
From $376 per night (USD)VRBO
From $335 per night (USD)Expedia
Gulf Watch 216 - Anna Maria Island - Condo 2 Bedroom / 2 Bath Gulf to Bay access, maximum occupancy of 4 people .
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Gulf Watch 216 - Anna Maria Island - 2 Bedroom / 2 Bath, maximum occupancy of 4 people. Direct Bay View - Heated Commun ...
From $335 per night (USD)Expedia
From $718 per night (USD)VRBO
Havana Cay- Adorable 3 bedroom cottage style- Pool/spa and only 4 houses from be
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Havana Cay 109 Cedar Ave, Anna Maria, FL 34216 What you will love about this property: • Historic 1924 Latin style home ...
From $718 per night (USD)VRBO
From $460 per night (USD)Expedia
Coco's Dream - Waterfront Home w/ Oversized Private Heated Pool, 5 Min to AMI
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our beautiful Coco's Dream, a canal front home located just 5 minutes from Anna Maria Island and its award-wi ...
From $460 per night (USD)Expedia
From $369 per night (USD)VRBO
Bayview Condo D - Anna Maria Island - Condo 2 Bedroom/ 2 Bath bay view, maximum occupancy of 4 people. Community pool. Distance to the Beach: 1 block
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Bayview Condo, Unit D - Anna Maria Island - 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Community Pool - Bay View ...
From $369 per night (USD)VRBO
From $527 per night (USD)Expedia
Private Pool 4 bd 3 ba with 2 King Master Suites Sleep 10 near AMI and IMG
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Private Pool home near Anna Maria Island & Sarasota. About 5 miles to Anna Maria Island and 23 miles to Siesta Key Beach ...
From $527 per night (USD)Expedia
From $307 per night (USD)VRBO
A Shore Thing - Relaxing Island Living , Large Heated Pool, Boat Lift
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beach house is "A Shore Thing" for creating fantastic vacation memories. This newly renovated ground level home is ...
From $307 per night (USD)VRBO
From $336 per night (USD)Expedia
JUST LISTED FOR SNOWBIRD 2026 SEASON-CLOSE TO BEACHES, SHOPS, RESTAURANTS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just listed for the SNOWBIRD season 2026. INQUIRE FOR WINTER RATES AND DATES. This spacious 2 BR split floor plan is loc ...
From $336 per night (USD)Expedia
From $1351 per night (USD)VRBO
Island Escape! Pool, Spa, Ping Pong and Fire Pit for Group Fun
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Sail Away by AMI Locals VR19-000048 Welcome to Sail Away, a spectacular six bedroom, six and a half bath canal-front ...
From $1351 per night (USD)VRBO
From $204 per night (USD)Expedia
Sunset Condo #156 on Anna Maria Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This totally renovated condo offers the Gulf of Mexico across the street (west) and Palma Sola Bay (east) of property wi ...
From $204 per night (USD)Expedia
From $557 per night (USD)VRBO
Beachfront Condo-Amazing Views of the Sunset from Every Room! 2 King/4 twins
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
GULF FRONT CONDO - Exquisite, newly constructed 3 bedroom 2 bath direct gulf front condo. Corner, end unit on top floor. ...
From $557 per night (USD)VRBO
From $273 per night (USD)Expedia
Lakeside Beach House · Pool · Outdoor Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC16-000807 3BR · 2BA · Sleeps 6 · Private Heated Pool · Outdoor Kitchen · Canal Fishing Pier · Beach Gear Provided · ...
From $273 per night (USD)Expedia
From $415 per night (USD)VRBO
Experience Coastal Vibes and Serenity - Your Ultimate Longboat Key Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover Paradise at Blue Heron House - Your Perfect Longboat Key Vacation Rental Welcome to Blue Heron House by RVA, a ...
From $415 per night (USD)VRBO
From $435 per night (USD)Expedia
Stunning 3Bed/3 Bath, Heated Pool, FREE WiFi, Close to Beach, On Canal to Dock your Boat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Pelican Point is a 3-bedroom, 3-bath canal-front home designed for a relaxed Florida vac ...
From $435 per night (USD)Expedia
From $332 per night (USD)VRBO
Updated 2B/2B with a beautiful view of the bay right from the patio!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy all Longboat Key has to offer from Harbor Villa Club! Beautifully updated 2/2 directly on the bay! Gorgeous views ...
From $332 per night (USD)VRBO
From $261 per night (USD)Expedia
LONGBOAT KEY BEAUTY! This 2/2 unit offers stunning views of the bay! Call today to book your fall vacation!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
• Carefree check-in, go straight to your unit no office visit required. • Fully Equipped Kitchen including microwave, st ...
From $261 per night (USD)Expedia
From $707 per night (USD)VRBO
Dix-Sea-Land Delight: Close to beach, private pool, quiet street
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Dix-Sea-Land Delight is a modern, well-appointed 3-bedroom, 3.5-bathroom retreat in Bradenton Beach, set on a quiet stre ...
From $707 per night (USD)VRBO
From $504 per night (USD)Expedia
Beachfront Paradise at Tiffany Place 213 | Heated Pool & Gulf Views | 2 Bd/2 Bath | FREE WIFI & Trolley | Awesome Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
**ASK ABOUT LAST MINUTE DEALS! Enjoy a relaxing beachfront getaway at Tiffany Place 213, a beautifully remodeled 2-bedr ...
From $504 per night (USD)Expedia
From $339 per night (USD)VRBO
Step from the Beach.Renovated ground Floor unit 63
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Completely renovated. Everything is new. Amazing location. Charming studio. This condo has patio. Condo management will ...
From $339 per night (USD)VRBO
From $1408 per night (USD)Expedia
Sea La Vie AM: Bay front, pool, hot tub, rooftop deck, and water sports gear!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
***Photos Updated September 2025*** Experience the ultimate waterfront getaway at this stunning bayfront property in Ann ...
From $1408 per night (USD)Expedia
From $856 per night (USD)VRBO
Beach Bay Serenity: Pine Ave canal front pool home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Beach Bay Serenity! This gorgeous 4 bedroom 3.5 bath waterfront home located on Pine Avenue is the perfect p ...
From $856 per night (USD)VRBO
From $523 per night (USD)Expedia
Beachfront - Sandy Turtle by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located on the tranquil beaches of Anna Maria Island, Sandy Turtle is mere steps away from the beach and offers pictures ...
From $523 per night (USD)Expedia
From $274 per night (USD)VRBO
251 Gorgeous lake view pool house with a golf membership
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gulf Coast Florida Properties would like to introduce the latest addition to our portfolio of vacation homes. 251 RIVER ...
From $274 per night (USD)VRBO
From $204 per night (USD)VRBO
Beach Waves-Private Beach Access-Heated Pool-Two Balconies-Free Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most ...
From $204 per night (USD)VRBO
From $283 per night (USD)VRBO
Bayview Inn #101 · Heated Pool · Bridge St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Bayview Inn #101 | Newly Remodeled & Steps from Bridge Street Welcome to Bayview Inn #101, a newly remodeled 1-bedroom, ...
From $283 per night (USD)VRBO
From $795 per night (USD)Expedia
Beautiful 1 Bedroom Condo with Beach Facing Balcony and Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconuts Beachfront #112 by AMI Locals VRC21-000175 Your dream beach vacation starts at Coconuts Beachfront #112, a ...
From $795 per night (USD)Expedia
From $256 per night (USD)VRBO
Serene Escape King Master, Minutes to AM Island, IMG & More
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
When you stay here you'll enjoy these serene and pastoral park-like grounds with non-stop views of catch and release fis ...
From $256 per night (USD)VRBO
From $466 per night (USD)Expedia
The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in Heart of AMI
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Cottage on Pine! On Anna Maria Island (Anna Maria, FL) The Space Step inside The Cottage on Pine and fee ...
From $466 per night (USD)Expedia
From $616 per night (USD)VRBO
Mango Bay – Luxury Island Home w/ Heated Pool, Spa & Walk To Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Mango Bay! On Anna Maria Island (Holmes Beach, FL) Set on a quiet street near the sand, Mango Bay blends ope ...
From $616 per night (USD)VRBO
From $755 per night (USD)Expedia
Bay beauty with heated pool, spa, games, ping pong
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning waterfront Anna Maria Island retreat perfect for families! Enjoy a private heated saltwater pool, hot tub, and ...
From $755 per night (USD)Expedia