Anna Maria Rentals
From $1638 per night (USD)VRBO
Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak, SUPs & MORE
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to the Rum Cove Experience! This magical home is a one-of-a-kind oasis 🌴 on a one-of-a-kind island located ri ...
From $1638 per night (USD)VRBO
From $380 per night (USD)Expedia
Over the Moon - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
“Over the Moon” located on the North end of Anna Maria is an adorable 3 bedroom, 2 bathroom cottage that spaciously acco ...
From $380 per night (USD)Expedia
From $610 per night (USD)VRBO
Quiet Canal Home, Walking Distance to Bay Beach, Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our Tern by Anna Maria Island Accommodations Anna Maria Vacation Home 111 Tern Dr, Anna Maria, FL 34216 VR22-000023 ...
From $610 per night (USD)VRBO
From $443 per night (USD)Expedia
Lovely island home - 1 block to Pine Street, 2 dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spring Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $443 per night (USD)Expedia
From $1544 per night (USD)VRBO
Banyan Beach: Steps to Beach, Pool, Game Room, Putting Green by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Banyan Beach by Anna Maria Life Vacation Rentals 104 Beach Ave, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $1544 per night (USD)VRBO
From $1267 per night (USD)Expedia
Snook Lookout: Canal Home, Pool, Game Room, Putting Green by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Snook Lookout by Anna Maria Life Vacation Rentals 211 Oak Ave, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $1267 per night (USD)Expedia
From $760 per night (USD)VRBO
Luxury 4-Bedroom Home Near Beach with Pool & Spa at Under The Sea, Anna Maria!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Under The Sea by AMI Locals 118 Peppertree Lane, Anna Maria, Florida VR17-000055 Welcome to Under The Sea! This stun ...
From $760 per night (USD)VRBO
From $853 per night (USD)Expedia
Stunning 5 bedroom Luxury home, Pool and Spa, beach VIEWS!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Coastal Queen by Anna Maria Island Locals Home in Anna Maria, FL Located just one street from the sugary white sands of ...
From $853 per night (USD)Expedia
From $1659 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Gulfview Estate, your exquisite beachfront retreat where luxury meets tranquility. This stunning 5-bedroom, 4 ...
From $1659 per night (USD)VRBO
From $385 per night (USD)Expedia
Beach N Bay 206 by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Beach N Bay 206! Pool COOLING for hot summer days! A honeymooners delight or a couple's retreat! ...
From $385 per night (USD)Expedia
From $824 per night (USD)VRBO
4 Beds 4.5 Bath with Pool 3 Blocks to Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
You won't be disappointed with this home! This 4 bedroom, 4.5 bathroom home is located in the heart on ANNA MARIA ISLAND ...
From $824 per night (USD)VRBO
From $932 per night (USD)Expedia
4 Bed 4.5 Bath Family Friendly, 3 Blocks to Gulf
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
You won't be disappointed with this brand home! This home has 4 bedrooms each with an en-suite washroom, home is located ...
From $932 per night (USD)Expedia
From $353 per night (USD)VRBO
Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cute Villa in the heart of Anna Maria! Palm Court Villas are located in the heart of Anna Maria Village with a short st ...
From $353 per night (USD)VRBO
From $580 per night (USD)Expedia
Stay at Spring Haven a Anna Maria Family Rental with Pool Near Beach & Pine Ave
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Spring Haven by AMI Locals Home in Anna Maria, Florida VR18-000154 Experience the perfect family vacation at Spring ...
From $580 per night (USD)Expedia
From $667 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to AMI Bay Breeze! This newly renovated, 3 bedroom 2 bathroom home is the perfect escape for your next vacation ...
From $667 per night (USD)VRBO
From $898 per night (USD)Expedia
Gorgeous island luxury home just one block to the Beach! Come stay with us!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Tahiti Bay by AMI Locals Home in Anna Maria, FL VR16-000466 Welcome to Tahiti Bay, a stunning vacation rental wi ...
From $898 per night (USD)Expedia
From $314 per night (USD)VRBO
Bay-facing condo with amazing views and heated pool - beach across the street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
South Bay Inn 2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $314 per night (USD)VRBO
From $796 per night (USD)Expedia
Salty C Cottage Spectacular canal front home with pool and hot tub!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Gorgeous and recently remodeled 4 bedroom, 3 1/2 bath ground level home with amazing designer touches and finishes throu ...
From $796 per night (USD)Expedia
From $427 per night (USD)VRBO
Sea Spray 5: *Heated Pool *Steps to beach *Close to shops and dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
**Photos Updated April 2025** The Sea Spray Cottages are an adorable group of Units located in the North End of Anna Mar ...
From $427 per night (USD)VRBO
From $837 per night (USD)Expedia
Golf Cart, Bimini Cove by SeaBreeze Vacation
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
A 6-person electric golf cart is included with any new reservation for this property! You must be 21 years old and show ...
From $837 per night (USD)Expedia
From $492 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
***Photos updated May 2025*** Leave the stress of everyday life and get "A Bay From it All"! This amazing 3 bedroom / 3 ...
From $492 per night (USD)VRBO
From $311 per night (USD)Expedia
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Open for business in 2025! We are ready to host you and your family!!MI Oasis Getaway is a true oasis on both the outsi ...
From $311 per night (USD)Expedia
From $342 per night (USD)VRBO
Ideal Location, Stunning Villa! Close to beach, beach gear provided!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
❗ Flexible check in days for most of the year--with the exception of holidays. Friday arrivals and departures during Pe ...
From $342 per night (USD)VRBO
From $668 per night (USD)Expedia
Luxury Home with Pool and Dock for Fishing!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Pelican's Nest by AMI Locals Home in Anna Maria, Florida VR20-000006 Experience the ultimate canal front escape at Peli ...
From $668 per night (USD)Expedia
From $383 per night (USD)VRBO
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Built in 1924, Sunset Cottages’ beautifully maintained woodwork coupled with updated amenities delivers an authentic Flo ...
From $383 per night (USD)VRBO
From $545 per night (USD)Expedia
Island Time: AMI North End, Pool, Close to City Pier & Pine Ave by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Time by Anna Maria Life Vacation Rentals 426 Spring Ave., Anna Maria, FL 34216 What You'll Love About This Home ...
From $545 per night (USD)Expedia
From $925 per night (USD)VRBO
Bean Point Beachfront- Beachfront 4 bedroom private home with pool/spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
At A Glance Gulf-Front, Beach side Home Spacious Backyard Deck with Covered Dining Area, TV & Gas BBQ Grill NEW Private ...
From $925 per night (USD)VRBO
From $672 per night (USD)Expedia
Golf Cart, Stonehenge 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. Driver's must provide valid ...
From $672 per night (USD)Expedia
From $725 per night (USD)VRBO
*NEWLY RENOVATED* Boutique Spanish-Style Villa - perfect for family & friends
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This unique, beautifully appointed Boutique Spanish Style Villa on the North End of Anna Maria Island is a perfect getaw ...
From $725 per night (USD)VRBO
From $149 per night (USD)Expedia
2nd-floor condo across the street from the beach with heated pool, balcony, W/D
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
South Bay Inn 4 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $149 per night (USD)Expedia
From $649 per night (USD)VRBO
Island Therapy: Pool, Canal, Dock, Outdoor Fun & Games!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Island Therapy by Anna Maria Life Vacation Rentals 103 Gull Drive, Anna Maria, FL 34216 What You'll Love About This Hom ...
From $649 per night (USD)VRBO
From $493 per night (USD)Expedia
Tinas Piece of Paradise - 4BR private pool home - Island Real Estate Vacations
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
When looking to accommodate a large group during you paradise Anna Maria Island vacation look no further than “Tina’s Pi ...
From $493 per night (USD)Expedia
From $812 per night (USD)VRBO
Reel Deal: Water Views, Elevator, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Reel Deal by Anna Maria Life Vacation Rentals 505 S Bay, Anna Maria, FL 34216 What You'll Love About This Home: Locatio ...
From $812 per night (USD)VRBO
From $795 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 $795 per night (USD)VRBO
Click For PricingVRBO
Blue Waters~Anna Maria, Private Home, Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Are you looking for Peace and Quiet and a place you can bring your dog too? Look no further than "Blue Waters." This lo ...
Click For PricingVRBO
From $603 per night (USD)Expedia
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. * Private ...
From $603 per night (USD)Expedia
From $808 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 ...
From $808 per night (USD)VRBO
From $301 per night (USD)Expedia
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
If you're longing to take a step back in time when Florida was about lazy beach days and ocean breeze evenings then look ...
From $301 per night (USD)Expedia
From $1049 per night (USD)VRBO
Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Welcome to Kay's Landing: A Breathtaking Retreat on Anna Maria Island Step into paradise at Kay's Landing, a stunning 6 ...
From $1049 per night (USD)VRBO
From $1449 per night (USD)Expedia
Brand new luxury Home! Canal Front with Pool, Spa, Rooftop Deck with views
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Shell We Dance by Anna Maria Island Accommodations Home in Anna Maria, Florida This immaculate canal-front home is a tr ...
From $1449 per night (USD)Expedia
From $315 per night (USD)VRBO
Steps away to beaches and the Gulf, snowbird friendly, AC, free WIFI and parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $315 per night (USD)VRBO
From $1368 per night (USD)Expedia
Sunset Reflections | LUXURY New Home, Private Pool, Spa, Rooftop, Game Room, and MORE!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sunset Reflections - A Prime Location with Spectacular Views Sunset Reflections is just a short stroll from the powdery ...
From $1368 per night (USD)Expedia
From $1882 per night (USD)VRBO
Mandalay Bay - Enjoy waterfront luxury at its finest!
- 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 $1882 per night (USD)VRBO
From $743 per night (USD)Expedia
Elevator - A Bean Point Paradise by SeaBreeze Vacation
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Get ready to pack your bags because you'll be escaping to a tranquil oasis nestled within a lush tropical backyard, wher ...
From $743 per night (USD)Expedia
From $901 per night (USD)VRBO
Isla Living 3 Bed / 2 bath / Waterfront / Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
** Damage from the storm restored! Open for Bookings! ** Your Private Oasis Awaits at Isla Living! Discover a haven of ...
From $901 per night (USD)VRBO
From $576 per night (USD)Expedia
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 $576 per night (USD)Expedia
From $742 per night (USD)VRBO
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 $742 per night (USD)VRBO
From $1192 per night (USD)Expedia
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 10109 Gulf Drive Anna Maria, FL 34216 Welcome to Siena Sky, a new four- ...
From $1192 per night (USD)Expedia
From $704 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 214 Fir Ave, Anna Maria, Florida Welcome to Emerald Shores! Your u ...
From $704 per night (USD)VRBO
From $357 per night (USD)Expedia
1 min to beach, Shared Pool! - Emerald Shores East
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Emerald Shores East by Anna Maria Island Accommodations Home in Anna Maria, Florida Prepare for an unforgettable vac ...
From $357 per night (USD)Expedia
From $481 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 $481 per night (USD)VRBO
From $568 per night (USD)VRBO
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 1 twin bed, this cozy r ...
From $568 per night (USD)VRBO
From $884 per night (USD)VRBO
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar
- 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 $884 per night (USD)VRBO
Click For PricingExpedia
Rooftop deck with Spectacular Beach Views - Sea Creatures Cottage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sea Creatures Cottage by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 Experience the ultimate beach ...
Click For PricingExpedia
From $1753 per night (USD)VRBO
Resort-Style Home with Lazy River Pool and Beach Views - Nautical Situation
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 8
Nautical Situation by Anna Maria Island Accommodations Home in Anna Maria, Florida Welcome to the Nautical Situation! ...
From $1753 per night (USD)VRBO
From $641 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 $641 per night (USD)Expedia
From $669 per night (USD)VRBO
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 $669 per night (USD)VRBO
From $344 per night (USD)Expedia
Beachside Duplex w/ Pool & Private Suite
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Emerald Shores West by Anna Maria Island Accommodations 214 Fir Ave, Anna Maria, Florida Welcome to Emerald Shores We ...
From $344 per night (USD)Expedia
From $584 per night (USD)VRBO
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 $584 per night (USD)VRBO
From $1098 per night (USD)Expedia
New Luxury Getaway on Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your vacation rental, a stunning home nestled in the heart of Anna Maria Island, where the serene intercoasta ...
From $1098 per night (USD)Expedia
From $482 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 $482 per night (USD)VRBO
From $1174 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 $1174 per night (USD)Expedia
From $757 per night (USD)VRBO
AMI Du Soleil | Steps to the Beach, Heated Pool, Anna Maria Island, IMG
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to 'AMI Du Soleil' a ‘friend of the sun’ by StayDream Vacations. ✨"Great hosts, great house, great location. ...
From $757 per night (USD)VRBO
From $873 per night (USD)Expedia
September Golf Cart Special
- 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 $873 per night (USD)Expedia
From $665 per night (USD)VRBO
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 $665 per night (USD)VRBO
From $545 per night (USD)Expedia
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 Home in Anna Maria, Florida Welcome to A Change in Latitude! This elevated three-bed ...
From $545 per night (USD)Expedia
From $727 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 $727 per night (USD)VRBO
From $1200 per night (USD)Expedia
Luxury Anna Maria Island Rental: Rooftop Deck, Pool, & Golf Cart at Deckadence
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Deckadance by AMI Locals Home in Anna Maria, FL 34216 Experience the ultimate getaway at Deckadance! This brand-new l ...
From $1200 per night (USD)Expedia
From $1121 per night (USD)VRBO
Exclusive Luxury Pool Home on Anna Maria Island, Steps to Bean Point Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Love Me Blue by AMI Locals 792 Jacaranda Rd. Anna Maria, FL 34216 Experience your vacation dreams at Love Me Blue! Th ...
From $1121 per night (USD)VRBO
From $965 per night (USD)Expedia
The Oasis at Palmetto – Coastal Chic Retreat w/ Heated Pool, Spa & Balconies, Steps to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Oasis at Palmetto! On Anna Maria Island (Anna Maria, FL) Experience unparalleled relaxation at this coas ...
From $965 per night (USD)Expedia
From $1037 per night (USD)VRBO
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 $1037 per night (USD)VRBO
From $549 per night (USD)Expedia
Castaway Cove - Short stays! AMI gem!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax with friends and family at Castaway Cove, a true piece of paradise located at the north end of Anna Maria Island n ...
From $549 per night (USD)Expedia
From $412 per night (USD)VRBO
September Golf Cart Special
- 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 $412 per night (USD)VRBO
From $438 per night (USD)Expedia
September Golf Cart Special
- 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 $438 per night (USD)Expedia
From $1143 per night (USD)VRBO
Compass Rose- 9 bedroom close to beach with rooftop
- 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 $1143 per night (USD)VRBO
From $796 per night (USD)Expedia
From Dusk Til Dune- Canal front
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
From Dusk ‘Til Dune 404 North Shore Dr, Anna Maria, FL 34216 What you will love about this property: • Luxury home with ...
From $796 per night (USD)Expedia
From $712 per night (USD)VRBO
Anna Maria Beach House- 5 bedrooms close to beach
- 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 $712 per night (USD)VRBO
From $1168 per night (USD)Expedia
Winding Waves- 9 bedrooms on canal
- 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 $1168 per night (USD)Expedia
From $451 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 $451 per night (USD)VRBO
From $624 per night (USD)Expedia
Luxury Coastal Retreat with Pool, Rooftop Deck and Prime
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
North End Escape by AMI Locals Luxury Coastal Retreat with Pool, Rooftop Deck and Prime North-End Location 800 Jacara ...
From $624 per night (USD)Expedia
From $910 per night (USD)VRBO
Costa Bella: 4-Bedroom Home with Private Pool & Spa, Close to Beach & Pine Ave
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Costa Bella by Anna Maria Island Accommodations 10107 Gulf Dr Anna Maria, Florida 34216 Your family’s dream vacation aw ...
From $910 per night (USD)VRBO
From $431 per night (USD)Expedia
Private Pool - Fern Cottage by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Fern Cottage, an exquisite elevated beach house located in the highly sought-after residential north end of A ...
From $431 per night (USD)Expedia
From $240 per night (USD)VRBO
Bay Cottage: Water Front!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
*As of May 2025, the dock is temporarily unavailable* Bay Cottage by AMI Locals 510 South Drive Unit B, Anna Maria, FL ...
From $240 per night (USD)VRBO
From $519 per night (USD)Expedia
Dock of the Bay: Waterfront Home! Perfect for Large Groups or Families in Anna M
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Dock of the Bay by AMI Locals Waterfront Duplex in Anna Maria Welcome to Dock of the Bay, a stunning waterfront duple ...
From $519 per night (USD)Expedia
From $348 per night (USD)VRBO
Heated Plunge Pool & Screened Lanai: 2BR/2BA Oasis Steps from North-End Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover your perfect Anna Maria Island hideaway in this bright and breezy 2-bedroom, 2-bath home—complete with a queen ...
From $348 per night (USD)VRBO
From $1298 per night (USD)Expedia
Luxury Beachfront Home! Steps to Beach and Shopping and Sweeping Bay Views!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
ANNA MARIA- SHORE IS PARADISE LOCATED JUST STEPS AWAY FROM THE BEACH AND SHOPPING! This luxury house on the bay features ...
From $1298 per night (USD)Expedia
From $778 per night (USD)VRBO
Sun and Spring by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sun and Spring is a brand-new luxury retreat on Anna Maria Island, offering refined coastal elegance just steps from Pin ...
From $778 per night (USD)VRBO
From $563 per night (USD)Expedia
4 bedroom, pet friendly, Anna Maria Island beach home, sleeps 8!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The flAMIngo house is a 4 bedroom, 2 bath Key West style beauty with all the comforts of home! Let's flamingo to the bea ...
From $563 per night (USD)Expedia
From $404 per night (USD)VRBO
Moon Shadow South - Bean Point 3bed - Powered by Island Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Moon Shadow South, a beautifully appointed 3-bedroom, 2-bathroom custom home on Anna Maria Island, where coas ...
From $404 per night (USD)VRBO
From $265 per night (USD)Expedia
September Golf Cart Special
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Barefoot Bungalow, a ground-level hideaway recently updated in early 2025. The open-concept living area welco ...
From $265 per night (USD)Expedia
From $371 per night (USD)VRBO
Lakeview Lookout - Canal Front Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to this charming 2-bed cottage on Anna Maria Island’s north end, sleeping 5. Enjoy canal views, a king bedroom wi ...
From $371 per night (USD)VRBO
From $675 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 $675 per night (USD)VRBO
From $476 per night (USD)VRBO
Everything inside is new and beachy! Two blocks to Bean Point Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our vacation home is two blocks to either the Gulf of Mexico or Tampa Bay…Bean Point Beach! We have remodeled the entire ...
From $476 per night (USD)VRBO
From $638 per night (USD)Expedia
Large Heated Pool, 2 Master Bedroom Suites, Very Close to Gulf Beach.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
'South Cay' is an absolutely beautiful house in "Anna Maria", on Anna Maria Island, Florida. How close to the beach? Th ...
From $638 per night (USD)Expedia
From $811 per night (USD)VRBO
AUGUST SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The home has a private be ...
From $811 per night (USD)VRBO
From $183 per night (USD)VRBO
Best Location on Island - Read Our Guest Reviews!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Seaside Views - Waterfront, Steps from Beach & Restaurants Best Location on Island - Read Our Guest Reviews! This wate ...
From $183 per night (USD)VRBO
From $676 per night (USD)VRBO
North end canal front home ,tiki hut, dock, pool, spa, beaches....
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Single family quiet vacation home on Lake La Vista has it all... Incredible view with Roser Church across the canal. Thi ...
From $676 per night (USD)VRBO
From $1124 per night (USD)VRBO
Spectacular Beachfront House with Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to 'Sky way view', one of the most exclusive homes on Anna Maria Island. It is located in one of the most specta ...
From $1124 per night (USD)VRBO
From $5570 per night (USD)VRBO
The Rod and Reel Resort
- Bedrooms:
- 8
- Bathrooms:
- 11
- Sleeps:
- 30
Welcome to the new and luxurious Rod and Reel Resort. We are pleased to offer our guests the finest and most inclusive e ...
From $5570 per night (USD)VRBO
From $668 per night (USD)Expedia
Jungalow Bay by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Jungalow Bay. Your Anna Maria Island adventure awaits you in this unique, modern Bohemian and Polynesian para ...
From $668 per night (USD)Expedia