Anna Maria Rentals
From $653 per night (USD)VRBO
Peace of Paradise: Pool Spa & Amazing Views of Tampa Bay
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Peace of Paradise by Anna Maria Life Vacation Rentals 604 North Bay Blvd, Anna Maria, FL 34216 What You'll Love About T ...
From $653 per night (USD)VRBO
From $545 per night (USD)Expedia
Tranquil Palm: Perfect north-end location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Tranquil Palm, your serene getaway on the enchanting Anna Maria Island! Nestled on a peaceful north-end stree ...
From $545 per night (USD)Expedia
From $573 per night (USD)VRBO
Marys Place Walk to the Beach and Pine Ave shops
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Indulge in the ultimate beach escape to “Mary’s Place” located on Los Cedros, a *premier location* just north of Pine Av ...
From $573 per night (USD)VRBO
From $642 per night (USD)Expedia
Walk to Beach! Pool, Patio and Palm Trees!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Coconut Palm Paradise by AMI Locals Escape to Coconut Palm Paradise, a beautifully designed three-bedroom, three-bath ...
From $642 per night (USD)Expedia
From $376 per night (USD)VRBO
Love Shack on the Water Most desirable location on AMI
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on Pine Ave just steps from shops, the General Store, restaurants, the pier, beach, pier fishing, and the trolle ...
From $376 per night (USD)VRBO
From $1156 per night (USD)Expedia
NEW Home w/Pool, Rooftop Deck, and Putting Green-Gone Gulfin'
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Gone Gulfin’ by AMI Locals Welcome to Gone Gulfin’, a brand new, five-bedroom, four and a half bath luxury beach home ...
From $1156 per night (USD)Expedia
From $656 per night (USD)VRBO
Sunrise Vista
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Sunrise Vista on gorgeous Anna Maria Island. Pack up the family car and head to Anna Maria Island's perfectly ...
From $656 per night (USD)VRBO
From $420 per night (USD)Expedia
Gorgeous Beach Home with heated pool and close to beach! Pet friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Absolutely beautiful monthly rental in highly sought after Holmes Beach on Anna Maria Island. If you are interested in ...
From $420 per night (USD)Expedia
From $1683 per night (USD)VRBO
Pier Pleasure - Anna Maria at it's finest! Pool, hot tub, beach, putting green
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Luxury abounds in this lovely home on the north end of Anna Maria. Every inch of this home was built in a well thought o ...
From $1683 per night (USD)VRBO
From $552 per night (USD)Expedia
Beachfront Home with Amazing Deck and Beach Views! -Low Tide
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Low Tide by AMI Locals Anna Maria Island Beachfront Cottage with Pool and Trolley Access VR21-000077 Welcome to Low T ...
From $552 per night (USD)Expedia
From $606 per night (USD)VRBO
Bayfront Escape with Stunning Water Views and Steps to Bean Point
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Seaside by Anna Maria Vacations Home in Anna Maria, FL VR16-000432 Welcome to Seaside, an elegant three bedroom, two ...
From $606 per night (USD)VRBO
From $995 per night (USD)Expedia
Fancy Flamingo: Canal Front, Dock, Heated Pool & Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Fancy Flamingo by Anna Maria Life Vacation Rentals 319 Hardin, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $995 per night (USD)Expedia
From $821 per night (USD)VRBO
Sea Glass on Park - 4Bed Pool Home - by Island Real Estate Vacations
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Newly built single-family home, just 6 houses from the beach access path. Ground floor: one-car garage, stunning pool, a ...
From $821 per night (USD)VRBO
From $431 per night (USD)Expedia
AMI Outpost - 3 Bed 2 Bath Elevated Home - by Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming elevated villa in the heart of Anna Maria with private heated pool and fenced yard. Short walk to City Pier and ...
From $431 per night (USD)Expedia
From $805 per night (USD)VRBO
Steps to Beach - Bean Point Residence Unit A by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Approximately 40 steps and you'll be at the beach entrance to Anna Maria's sandy, white beach. This property offers conv ...
From $805 per night (USD)VRBO
From $621 per night (USD)Expedia
Steps to Beach - Bean Point Residence Unit B by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
For our beachgoer guests, the beach entrance to Anna Maria's sandy, white beaches are approximately 40 steps away. Bean ...
From $621 per night (USD)Expedia
From $1575 per night (USD)VRBO
Rooftop Deck, Private Pool and Game room! Perfect for Families!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Boundless Waves by Exclusive Vacations VR24-000005 Welcome to Boundless Waves, part of our Exclusive Collection. Offe ...
From $1575 per night (USD)VRBO
From $458 per night (USD)Expedia
Bimini Bay: 3 Blocks to Beach! Private Pool! by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bimini Bay by Anna Maria Life Vacation Rentals 312 Hardin Ave, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $458 per night (USD)Expedia
From $941 per night (USD)VRBO
Water's Edge: Dog Friendly, Canal Front, Dock & Pool & Spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Water's Edge by Anna Maria Life Vacation Rentals 221 Oak, Anna Maria, FL 34216 What You'll Love About This Home: Locati ...
From $941 per night (USD)VRBO
From $750 per night (USD)VRBO
Cedar Sunsets - 4 bed, 4 bath, Beach Block
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Make memories at this beautiful, new beach home with private pool. Only 4 houses to the beautiful white sand beaches of ...
From $750 per night (USD)VRBO
From $1179 per night (USD)VRBO
Brand New Luxury Home, Incredible Rooftop Deck and Pool! - Total Package
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Total Package by AMI Locals Welcome to Total Package by AMI Locals, a brand-new luxury beach home on the North End of ...
From $1179 per night (USD)VRBO
From $642 per night (USD)Expedia
Becker's Beach Bungalow by A Shore Thing Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your dream getaway at Anna Maria Island! Nestled just one block away from the pristine shores of the beach, t ...
From $642 per night (USD)Expedia
From $875 per night (USD)VRBO
\"Walk On The Beach \" house~3 bed, heated pool, 3min walk to the Bean Point Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to "Walk on the Beach " quiet and perfectly located at the North end of Anna Maria Island, 3 bedroom 2 bath pool ...
From $875 per night (USD)VRBO
From $652 per night (USD)Expedia
Sea Mist by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover Sea Mist, an exquisite coastal retreat nestled in the heart of Anna Maria Island. With its prime North end loca ...
From $652 per night (USD)Expedia
From $974 per night (USD)VRBO
Jersey Girl by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to this unique 5 bedroom Island Paradise!Jersey Girl features a main house with 3 bedrooms and 2 baths along wit ...
From $974 per night (USD)VRBO
From $1149 per night (USD)Expedia
Island Time on Cedar: 3 Houses to Beach! Dog Friendly! Games Galore! Heated Pool by Anna Maria Life
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Island Time on Cedar by Anna Maria Life Vacation Rentals 110 Cedar Ave, Anna Maria, FL 34216 What You'll Love About Thi ...
From $1149 per night (USD)Expedia
From $424 per night (USD)VRBO
Barefoot Mermaid 3, steps to the beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to “Barefoot Mermaid 3” a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria I ...
From $424 per night (USD)VRBO
From $765 per night (USD)Expedia
Luxury coastal home pool/spa, 1 block downtown AMI Pine Ave & 0.2 mi to beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Immerse yourself in coastal luxury at this exceptional 3-bedroom, 3.5-bathroom custom home, where opulent high-end finis ...
From $765 per night (USD)Expedia
From $598 per night (USD)VRBO
White Palms by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Introducing White Palms, an exquisite coastal retreat nestled in the coveted north end of Anna Maria Island. *Features ...
From $598 per night (USD)VRBO
From $1083 per night (USD)Expedia
Tropical Oasis -5 bedrooms with stunning Backyard with a Pool and close to beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Tropical Oasis 122 White Avenue, Anna Maria, FL 34216 What you will love about this property: • Less than one minute wa ...
From $1083 per night (USD)Expedia
From $739 per night (USD)VRBO
Casa Campoamor- 4 bedrooms and steps from beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Camp Campoamor 11107 Gulf Drive, Anna Maria, FL 34216 What you will love about this property: • Brand new renovations!! ...
From $739 per night (USD)VRBO
From $1012 per night (USD)Expedia
Beach Bliss | Waterfront Pool & Spa | Dock, Golf Cart & Boat Lift
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Escape to Beach Bliss, a stunning 4-bedroom, 3-bath waterfront home on Anna Maria Island. Enjoy the perfect bl ...
From $1012 per night (USD)Expedia
From $1198 per night (USD)VRBO
Casa Cay by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Casa Cay! This Bay front pool home on Anna Maria Island is an absolute paradise! With its prime location on t ...
From $1198 per night (USD)VRBO
From $452 per night (USD)Expedia
Historic AMI Charm, Steps from the Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Property Highlights • Short stroll to the Gulf Beaches • Historic 1925 beach cottage full of character • 2 Bedrooms | 2 ...
From $452 per night (USD)Expedia
From $2875 per night (USD)VRBO
Lap of Luxury by Duncan Real Estate
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Lap of Luxury!This home is new as of 2022 and has been meticulously built and designed to create a space for ...
From $2875 per night (USD)VRBO
From $2895 per night (USD)Expedia
Shangri-La | Bean Point | Rooftop Pool | Golf Cart
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 8
Summary: Escape to Shangri-La, a stunning beachfront estate on Anna Maria Island's coveted Bean Point. This private, ga ...
From $2895 per night (USD)Expedia
From $1768 per night (USD)VRBO
Experience Luxury at Go with the Flow! Lazy River Pool, Rooftop Deck and Games!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Go with the Flow by Exclusive Vacations Vacation Rental License #VR24-000026 Welcome to Go with the Flow, an exceptiona ...
From $1768 per night (USD)VRBO
From $1880 per night (USD)Expedia
Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
🌴 Kay's Landing | Rooftop Deck + Heated Pool & Spa 💖 Why You'll Love This Home Wake up to the coastal charm of Anna M ...
From $1880 per night (USD)Expedia
From $3006 per night (USD)VRBO
Sunset Reflections | LUXURY Home, Private Pool, Spa, Rooftop, Game Room, and MORE!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
🌴 Sunset Reflections | Heated Pool, Rooftop Terrace & Game Room, Steps to Gulf & Bean Point 💖 Why You'll Love This Ho ...
From $3006 per night (USD)VRBO
From $1036 per night (USD)Expedia
AMI Escape! Swim-Up Bar, Ping Pong, Spa and Walk to Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The James by AMI Locals Welcome to The James by AMI Locals, your ultimate North End beach getaway on Anna Maria Island ...
From $1036 per night (USD)Expedia
From $789 per night (USD)VRBO
Pelican Lagoon: *Heated Pool *Canal-front *Dock *Steps to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**Photos Updated April 2025** Welcome to Pelican Lagoon, your ultimate beachside haven on the desirable north end of Ann ...
From $789 per night (USD)VRBO
From $2115 per night (USD)Expedia
Mandalay Bay - Luxury 7 bedroom-Waterfront, large pool/spa and dock!!
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 18
At A Glance Heated pool with massive 12 person hot tub Newly renovated throughout- Luxury interior at it's finest 7 be ...
From $2115 per night (USD)Expedia
From $625 per night (USD)VRBO
Jacaranda Beach House - Privat pool - by Island Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to Jacaranda Beach House, a serene slice of island life located in the tranquil North End of Anna Maria Island. J ...
From $625 per night (USD)VRBO
From $839 per night (USD)Expedia
Villa Livella by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Livella is an elegant Island property that promises an unforgettable experience. The 3 bedrooms and 2 bath pool ho ...
From $839 per night (USD)Expedia
From $1311 per night (USD)VRBO
New Luxury Home with Beach Views and Pool, 1 min to Beach - Siena Sky
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Siena Sky by Anna Maria Island Accommodations Welcome to Siena Sky, a four-bedroom, four-bath luxury vacation home jus ...
From $1311 per night (USD)VRBO
From $628 per night (USD)Expedia
Sapphire Gulf: 5 houses to Gulf! Pool, Putting Green by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Sapphire Gulf by Anna Maria Life Vacation Rentals 117 Peppertree Lane, Anna Maria, FL 34216 What You'll Love About This ...
From $628 per night (USD)Expedia
From $724 per night (USD)VRBO
Beachside Duplex with Pool, Gulf Views and Steps to Pine Ave
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 8
Emerald Shores by Anna Maria Island Accommodations Welcome to Emerald Shores, a six-bedroom, four-bath duplex vacation ...
From $724 per night (USD)VRBO
From $737 per night (USD)Expedia
Emerald Shores East! Walk to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Emerald Shores East by Anna Maria Island Accommodations Welcome to Emerald Shores East, a three-bedroom, two-bath coas ...
From $737 per night (USD)Expedia
From $568 per night (USD)VRBO
Rainbow Reef: Close to Bean Point, Pool, Game Room by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Rainbow Reef by Anna Maria Life Vacation Rentals 720 Holly Rd, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $568 per night (USD)VRBO
From $511 per night (USD)Expedia
Charming 3-bedroom house in Anna Maria with Private Pool & Spa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this lovely house in picturesque Anna Maria. With 3 bedrooms including 2 king beds and 2 twin beds, this cozy ...
From $511 per night (USD)Expedia
From $1069 per night (USD)VRBO
Bean Point/Heated Pool/Spa/Bistro, Golf Cart Promo
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Enjoy breathtaking views of Egmont Key, Tampa Bay, and the Gulf of Mexico right from your doorstep! Walk straight ahead ...
From $1069 per night (USD)VRBO
From $352 per night (USD)Expedia
Rose Quartz: 2.5 Blocks to Beach! Pool & Spa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Rose Quartz by Anna Maria Life Vacation Rentals 308 Magnolia, Anna Maria, FL 34216 What You'll Love About This Home: Lo ...
From $352 per night (USD)Expedia
From $775 per night (USD)VRBO
Beachside Duplex w/ Pool and Private Suite
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Emerald Shores West by Anna Maria Island Accommodations Welcome to Emerald Shores West, a charming three-bedroom, two- ...
From $775 per night (USD)VRBO
From $596 per night (USD)Expedia
Manatee Manor by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the ultimate retreat at Manatee Manor, a dream vacation rental nestled in the highly sought-after North End of ...
From $596 per night (USD)Expedia
From $830 per night (USD)VRBO
Lakeview Hideaway - Waterfront Anna Maria
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
**Welcome to Lakeview Hideaway! A serene and beautifully appointed retreat on the north end of Anna Maria Island.** - L ...
From $830 per night (USD)VRBO
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Bean Point Bliss 3 Bedroom Home by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 1
<p>Located in Anna Maria, this welcoming vacation home lets you experience it all. There's convenient onsite parking, so ...
Click For PricingExpedia
From $653 per night (USD)VRBO
Bean Point Bliss by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Bean Point Bliss! This stunning 3-bedroom, 2-bathroom pool home has plenty of room for the whole family. Bean ...
From $653 per night (USD)VRBO
From $360 per night (USD)Expedia
Rainbow Fish: 1.5 blocks to beach! Pool, Spa & Game Room
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Rainbow Fish by Anna Maria Life Vacation Rentals 210 Archer Way, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $360 per night (USD)Expedia
From $510 per night (USD)VRBO
Family Getaway at A Change in Latitude: Private Pool, Games, 5 Mins to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
A Change in Latitude by AMI Locals Welcome to A Change in Latitude, a beautiful three bedroom, three bath elevated vac ...
From $510 per night (USD)VRBO
From $789 per night (USD)Expedia
Coral Reef: 50ft to Beach, Games Galore, Rooftop Deck, Pool, Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Coral Reef by Anna Maria Life Vacation Rentals 118 Mangrove Ave, Anna Maria, FL 34216 What You'll Love About this House ...
From $789 per night (USD)Expedia
From $641 per night (USD)VRBO
AMI Du Soleil | 1 Block 2 Beach, Big Heated & Shaded Saltwater Pool, Lanai, Grill, Walk to Restaurants, Cafes, Shops, Bars
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to 'AMI Du Soleil' a ‘friend of the sun’ by StayDream Vacations. If an official hurricane warning is issued f ...
From $641 per night (USD)VRBO
From $1123 per night (USD)Expedia
Dockside Dream: Luxury canal front home, dock, pool, spa and more!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Dockside Dream is a luxurious canal-front retreat on beautiful Anna Maria Island. This stunning 4-bedroom, 4.5-bathroom ...
From $1123 per night (USD)Expedia
From $1156 per night (USD)VRBO
The 19th Hole | AMI Beach Home, Private Heated Pool & Spa, Putting Green, Walk to Bay & Gulf Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The 19th Hole | AMI Beach Home, Private Heated Pool & Spa, Putting Green, Walk to Bay & Gulf Beaches Why You'll Love Th ...
From $1156 per night (USD)VRBO
From $1354 per night (USD)Expedia
Pool/Spa - Bean Point Retreat by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $1354 per night (USD)Expedia
From $808 per night (USD)VRBO
Magnolia Cottage: Private Pool, Near Beaches & Pine Ave
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Photos Updated November 2024! Magnolia Cottage is your perfect escape to Anna Maria Island, combining the charm of coast ...
From $808 per night (USD)VRBO
From $1308 per night (USD)Expedia
Luna Sea | Anna Maria Beach Home Rental - Steps from the Sea!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Luna Sea – Your Private Slice of Paradise on Anna Maria Island! Escape to a serene coastal haven just 100 ste ...
From $1308 per night (USD)Expedia
From $752 per night (USD)VRBO
Anna Maria Island of Palms - HotTub,Pool,Poker,Games and more
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to ISLAND OF PALMS – Your Ultimate Vacation Retreat! Escape to this stunning 5-bedroom, 3-bathroom coastal home ...
From $752 per night (USD)VRBO
From $658 per night (USD)Expedia
Bikini's & Martini's Waterfront Canal: 1 Block to Beach! Dock! On Canal! Anna Maria Life
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bikini's & Martini's Waterfront Canal by Anna Maria Life Vacation Rentals 215 Chilson Ave, Anna Maria, FL 34216 Locatio ...
From $658 per night (USD)Expedia
From $648 per night (USD)VRBO
Wade N' Sea: On Canal, North End, 1 Block to Pine by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Wade 'N Sea by Anna Maria Life Vacation Rentals 104 Gull Dr, Anna Maria, FL 34216 What You'll Love About This Home: Rec ...
From $648 per night (USD)VRBO
From $1042 per night (USD)Expedia
Family-Friendly Canal Retreat with Pool and Steps to the Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Coco Cottage by Anna Maria Island Accommodations VR23-000041 Welcome to Coco Cottage, a charming three-bedroom, three ...
From $1042 per night (USD)Expedia
From $863 per night (USD)VRBO
Sea La Vie - Custom Home w/ Pool, Spa & Rooftop Deck on Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Sea La Vie! On Anna Maria Island (Anna Maria, FL) The Space Where light dances across the water and modern d ...
From $863 per night (USD)VRBO
From $985 per night (USD)Expedia
Anna Maria Home with Pool and Rooftop Deck! 5-min Walk to Beach - Coconut Breeze
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Coconut Breeze Estate by Anna Maria Island Accommodations Escape to Coconut Breeze Estate, your ultimate four-bedroom, ...
From $985 per night (USD)Expedia
From $1491 per night (USD)VRBO
Rooftop Views! Pool, Spa and Game Room!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Love Me Blue by Exclusive Vacations VR24-000043 Welcome to Love Me Blue, part of our Exclusive Collection. This luxur ...
From $1491 per night (USD)VRBO
From $1602 per night (USD)Expedia
Bayfront Luxury | Rooftop Spa, Resort Pool + Golf Cart
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Deckadence by Exclusive Vacations Bayfront Luxury | Rooftop Spa, Resort Pool + Golf Cart VR25-000002 Welcome to Deck ...
From $1602 per night (USD)Expedia
From $1009 per night (USD)VRBO
Heavenly Hideaway, 3-bdrm house 5 min walk to the beach in beautiful Anna Maria
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Heavenly Hideaway, a Newly Renovated, exquisite canal-front vacation home featuring three bedrooms and three ...
From $1009 per night (USD)VRBO
From $667 per night (USD)Expedia
Golf Cart - Beach Escape by SeaBreeze Vacation
- Bedrooms:
- 2
- 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 $667 per night (USD)Expedia
From $792 per night (USD)VRBO
Blue Mermaid Beach Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Highlights - 2 minute walk to the Beach of Anna Maria Island - 5 minute walk to Pine Ave. • Private Pool • Outdoor Showe ...
From $792 per night (USD)VRBO
From $1909 per night (USD)Expedia
Coastal Elegance! Pool, Putting Green, Movie Room, and More!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Periwinkle Place by Exclusive Vacations VR25-000004 Indulge in the ultimate luxury beach home at Periwinkle Place, pa ...
From $1909 per night (USD)Expedia
From $867 per night (USD)VRBO
Salt Dreams: 1 Block to Beach! Pool, Spa, Games, Rooftop Deck by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Salt Dreams by Anna Maria Life Vacation Rentals 836 N Shore, Anna Maria, FL 34216 What You'll Love About This Home: Loc ...
From $867 per night (USD)VRBO
From $1417 per night (USD)Expedia
Luxury Beach House with Bay Views and Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Glass House by the Beach, a luxurious modern vacation retreat on Anna Maria Island, designed to immerse y ...
From $1417 per night (USD)Expedia
From $313 per night (USD)VRBO
The Twins: Your Perfect Budget Beach Getaway!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Photos Updated March 2025! Looking for a cozy, budget-friendly escape just steps from the beach? The Twins is the spot ...
From $313 per night (USD)VRBO
From $427 per night (USD)Expedia
Fish, Swim & Unwind: Anna Maria Apt Steps to Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Private Outdoor Shower | 11 Mi to Downtown Bradenton | 2 Blocks to Palmetto Ave Beach Indulge in the island getaway of ...
From $427 per night (USD)Expedia
From $456 per night (USD)VRBO
2 Blocks to Beach: Tropical Retreat in Anna Maria
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Outdoor Shower | Perfect Place to Fish, Swim & Unwind | 11 Mi to Downtown Bradenton Indulge in the island getaway of yo ...
From $456 per night (USD)VRBO
From $507 per night (USD)Expedia
Book Magnolia Shores: Family-Friendly Getaway Near Beach with Pool and Mini Golf
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Magnolia Shores by Anna Maria Island Accommodations Welcome to Magnolia Shores, a renovated two-bedroom, one-bath coas ...
From $507 per night (USD)Expedia
From $617 per night (USD)VRBO
Paradise Pointe by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to your private waterfront oasis on Anna Maria Island at Paradise Pointe. *Features include* * Canal front wit ...
From $617 per night (USD)VRBO
From $1614 per night (USD)Expedia
Dolce Vita: Amazing Rooftop Experience, Views, Pool, Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Dolce Vita by Anna Maria Life Vacation Rentals 848 N Shore Drive, Anna Maria, FL 34216 What You'll Love About This Home ...
From $1614 per night (USD)Expedia
From $693 per night (USD)VRBO
Dock of the Bay by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Dock of the Bay!Located on the North end of Anna Maria, Dock of the Bay is a newly remodeled two- bedroom, th ...
From $693 per night (USD)VRBO
From $990 per night (USD)Expedia
Castle Azul: Luxury canal front w/pool, hot tub, putting green, and ping pong
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Photos updated April 2025! Welcome to Castle Azul, a stunning canal-front vacation home on Anna Maria Island! Just one ...
From $990 per night (USD)Expedia
From $858 per night (USD)VRBO
160 ft canal front, 2 boat lifts, cool- pool, cool mister-system, putting green
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to a beautiful 4-bedroom house in Anna Maria for a wonderful getaway. Relax in a backyard paradise with moder ...
From $858 per night (USD)VRBO
From $772 per night (USD)Expedia
Holly Hideaway: Spacious 2 bed, heated pool, screened lanai, 5-mins to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Holly Hideaway, your peaceful retreat nestled in a quiet neighborhood on the desirable North end of Anna Mari ...
From $772 per night (USD)Expedia
From $1126 per night (USD)VRBO
Mintfish: Luxury canal-front w/heated pool, hot tub, docks, and water views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Mintfish, your peaceful canal-front retreat tucked away on the north end of Anna Maria Island. This ground-le ...
From $1126 per night (USD)VRBO
From $576 per night (USD)Expedia
AMI Swedish Beach House: Bay Front! Overlooking Tampa Bay! by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
AMI Swedish Beach House by Anna Maria Life Vacation Rentals 306 S Bay Blvd, Anna Maria, FL 34216 What You'll Love About ...
From $576 per night (USD)Expedia
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Luxury North End Escape | 3 king beds + pool/spa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
⭐️Super host Property + Verified for Cleanliness + Communication⭐ 📍228 Gladiolus Street - `Castaway Cove` 🌊 Castaway C ...
Click For PricingVRBO
From $700 per night (USD)Expedia
Coconut Tree: Canal-Front Home, Dock, Heated Pool & Covered Lanai
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Coconut Tree – your tropical retreat on Anna Maria Island, recently updated with all-new furnishings for your ...
From $700 per night (USD)Expedia
From $1587 per night (USD)VRBO
Compass Rose- Luxury 9 bedroom close to beach with rooftop, pool and spa
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 18
Compass Rose 9407 Gulf Drive, Anna Maria, FL 34216 What you will love about this property: • Luxury home with luxury fin ...
From $1587 per night (USD)VRBO
From $756 per night (USD)Expedia
From Dusk Til Dune- 5 bedroom, Canal front, private pool/spa and close to beach
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
From Dusk ‘Til Dune 404 North Shore Dr, Anna Maria, FL 34216 What you will love about this property: • Luxury home with ...
From $756 per night (USD)Expedia
From $980 per night (USD)VRBO
Anna Maria Beach House- 5 bedrooms close to beach- Private pool and spa
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Anna Maria Beach House 212 Spring Avenue, Anna Maria, FL 34216 What you will love about this property: • Luxury home wit ...
From $980 per night (USD)VRBO
From $1587 per night (USD)Expedia
Winding Waves- Luxury 9 bedrooms on canal with large pool and spa!!
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 18
Winding Waves 9403 Gulf Dr, Anna Maria, FL 34216 What you will love about this property: • Luxury home with luxury fini ...
From $1587 per night (USD)Expedia
From $576 per night (USD)VRBO
Private Pool - Island Dream
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Island Dream is your perfect coastal escape. This spacious 4-bedroom, 4-bathroom coastal retreat with a fully equipped k ...
From $576 per night (USD)VRBO
From $1044 per night (USD)Expedia
Luxury Coastal Retreat with Pool and Rooftop Deck!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
North End Escape by AMI Locals Welcome to North End Escape, a stylish three-bedroom, two-bath custom built home in one ...
From $1044 per night (USD)Expedia