Anna Maria Rentals
From $565 per night (USD)VRBO
Dreamscape: North End Pool Home, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Dreamscape by Anna Maria Life Vacation Rentals 773 Jacaranda Rd, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $565 per night (USD)VRBO
From $1036 per night (USD)Expedia
5 O'Clock Somewhere: Dog Friendly Canal Front, Elevator, Pool, Beach 2 Blocks by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
5 O'Clock Somewhere by Anna Maria Life Vacation Rentals 216 Chilson, Anna Maria, FL 34216 What You'll Love About This H ...
From $1036 per night (USD)Expedia
From $232 per night (USD)VRBO
Ground-floor home with fast WiFi, shared pool, & central AC - close to beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Villas, Condo 1A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $232 per night (USD)VRBO
From $304 per night (USD)Expedia
Beach N Bay 204 by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Beach N Bay 204! A honeymooners delight or a couple's retreat! Enjoy a romantic getaway! Don't miss your ch ...
From $304 per night (USD)Expedia
From $297 per night (USD)VRBO
Charming Ground Floor Condo with Shared Pool, High-Speed WiFi, and Central AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Beach Villa 1B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $297 per night (USD)VRBO
From $1084 per night (USD)VRBO
North End AMI, Pool,Ocean Views,Tropical Oasis and elevator. No hurricane Damage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
No hurricane damages to the house. This home is a showcase stunner! Sea Breeze was has been remodeled and professional ...
From $1084 per night (USD)VRBO
From $1189 per night (USD)VRBO
Large Home Directly on the Beach - By Island Real Estate Vacations
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Family friendly with fantastic views and directly on the Gulf of Mexico sound like your idea of a perfect vacation renta ...
From $1189 per night (USD)VRBO
From $1178 per night (USD)Expedia
Luxury Island Escape with Pool, Swim-Up Tiki Bar, Game Room and Rooftop Deck
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 16
Tropical Oasis by Anna Maria Island Accommodations Holmes Beach 204 72nd St VRC18-000061 Welcome to Tropical Oasi ...
From $1178 per night (USD)Expedia
From $884 per night (USD)VRBO
Home just steps to BEACH! Private pool and spa - Sign of the Mermaid
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Sign of the Mermaid by AMI Locals Home in Anna Maria, Florida VR17-000054 Welcome to Sign of the Mermaid, a luxurious ...
From $884 per night (USD)VRBO
From $685 per night (USD)Expedia
Mainsail Beach Inn 2 Bedroom
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The stunning interiors in your private Holmes Beach vacation rental are elegant, fresh and bright. The two bedroom, 2.5 ...
From $685 per night (USD)Expedia
From $994 per night (USD)VRBO
The Perfect Gulf Front Vacation, Directly on the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Osprey House, Gulf front vacation rental-located on the North end of Anna Maria Island. Located directly on t ...
From $994 per night (USD)VRBO
From $939 per night (USD)Expedia
Jacaranda Gem by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Take a break from the hustle and bustle, and relax in the calm and serene atmosphere of this spotless vacation home. Jac ...
From $939 per night (USD)Expedia
From $934 per night (USD)VRBO
Ocean Walk- 5 bedroom heated pool/spa and 6 houses from the white sandy beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
At A Glance North-facing private heated pool with a spa Steps to the beach Loft and bonus rec room by the pool Part of o ...
From $934 per night (USD)VRBO
From $939 per night (USD)Expedia
Coastal Bliss- 2-Minute Walk (500 Feet) to the beach with private pool and spa
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
At A Glance 2-Minute Walk (500 Feet) to the Beach! Private Pool and Outdoor Spa, Heated Seasonally Outdoor Bar and Pool ...
From $939 per night (USD)Expedia
From $711 per night (USD)VRBO
Private Tropical Oasis - Tarpon Point - Pool/Spa, Perfect Island Getaway!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to this charming 3 bedroom, 2 bathroom island oasis nestled into a corner lot within walking distance to The Gulf ...
From $711 per night (USD)VRBO
From $502 per night (USD)Expedia
BEST LOCATION! NORTH END OF ANNA MARIA, FL STEPS TO BEACH & DINING - LOWER UNIT
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Location!!! North end of Anna Maria Island . Steps to the Bean Point Beach and everything you need for your perfect Anna ...
From $502 per night (USD)Expedia
From $405 per night (USD)VRBO
Twin Palms: Big House Close to Beach, Heated Lagoon Pool, Infant/Pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Stay at the home of a NY Times best-selling food writer and her architectural designer/tech husband! Pet friendly, lots ...
From $405 per night (USD)VRBO
From $533 per night (USD)Expedia
The Palm Leaf by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Palm Leaf is a newly remodeled three-bedroom, two-bathroom private home with a pool and spa. This fabulous house is ...
From $533 per night (USD)Expedia
From $471 per night (USD)VRBO
LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Location, Location, Location.... recently remodeled and improved after storms... surrounded by multi million dollar home ...
From $471 per night (USD)VRBO
From $548 per night (USD)Expedia
The Salted Coconut by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
The Salted Coconut is just a short stroll to the beautiful beaches of Anna Maria! This gorgeous home is a 3-bedroom, 3-b ...
From $548 per night (USD)Expedia
From $490 per night (USD)VRBO
Pure Bliss: Heated Pool, Lanai, Walk to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
***Photos Updated June 2025*** This newly renovated 2-bedroom, 2-bathroom cottage truly lives up to its name. Completed ...
From $490 per night (USD)VRBO
From $602 per night (USD)Expedia
Mermaid Cove: Updated Forida Cottage w/pool, hot tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
You'll fall in love with Mermaid Cove the second you step inside. This beautifully refurbished property boasts all the m ...
From $602 per night (USD)Expedia
From $1261 per night (USD)VRBO
South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Photos updated March 2025! Newly redesigned in 2025, this stunning 4-bedroom, 3.5-bathroom beach house offers the perfe ...
From $1261 per night (USD)VRBO
From $648 per night (USD)Expedia
Canal front pool home on the north end of Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
What more could you want from a vacation rental then a beautiful Mediterranean inspired canal home nestled into the priv ...
From $648 per night (USD)Expedia
From $476 per night (USD)VRBO
Cozy Cottage w private Beach Access, AC&WiFi - NorthEnd AMI. No hurricane damage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
No hurricane damages! We have replanted the damaged landscape and fence. Sea Garden Cottage is a true island gem and e ...
From $476 per night (USD)VRBO
From $603 per night (USD)Expedia
A Wave From It All – Pool, Cabana, Putting Green & Pet-Friendly Oasis on AMI
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to A Wave From It All! On Anna Maria Island (Anna Maria, FL) Your AMI Getaway Awaits: A Pet-Friendly Oasis With ...
From $603 per night (USD)Expedia
From $912 per night (USD)VRBO
Stylish Coastal Escape with Pool Near Beach and Trolley
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Take Me Away by AMI Locals 214 69th Street, Holmes Beach, FL 34217 VRC20-000170 Escape to Take Me Away, a beautiful ...
From $912 per night (USD)VRBO
From $1004 per night (USD)Expedia
Yellowbird: AMI North End, Gulf Views, Pool, Tiki Hut, Elevator by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Yellowbird by Anna Maria Life Vacation Rentals 705 North Shore Dr., Anna Maria, FL 34216 What You'll Love About This Ho ...
From $1004 per night (USD)Expedia
From $356 per night (USD)VRBO
Bay Breeze Cottages #1 (The Mahi-Mahi)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the ...
From $356 per night (USD)VRBO
From $246 per night (USD)Expedia
⚓3/2.5 Private Canal Front Pool Home on AMI⚓Close To Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Location, Location (see map): There are seven miles of pristine, quartz sand beaches shimmering along our island and you ...
From $246 per night (USD)Expedia
From $625 per night (USD)VRBO
Hawaiian Punch -3 Blocks to Beach, Pool, Dock on Canal, Dog Friendly by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Hawaiian Punch by Anna Maria Life Vacation Rentals 125 Crescent Drive, Anna Maria, FL 34216 What You'll Love About This ...
From $625 per night (USD)VRBO
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Snail's Pace: North End on Canal, Kayaks & Dog Friendly by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Snail's Pace by Anna Maria Life Vacation Rentals 606 N. Shore Drive, #4, Anna Maria, FL 34216 What You'll Love About Th ...
Click For PricingExpedia
From $2101 per night (USD)VRBO
Spoil yourself! Gulf front, heated pool, hot tub. Front row for sunsets-perfect!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Holiday dates at Nest on the Beach are open! If sugar-white sand between your toes, waves that sing you to sleep, and s ...
From $2101 per night (USD)VRBO
From $979 per night (USD)VRBO
Beachfront Mango Beach House on Bean Point in Anna Maria Florida
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Mango Beach House is an exceptional beach front paradise. White sugar sand, warm waters of the Gulf of Mexico are out y ...
From $979 per night (USD)VRBO
From $442 per night (USD)VRBO
Ebb Tide by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Come to this Island home and have a vacation of a lifetime! Totally remodeled, this 3-bedroom, 3-bath pool home is well ...
From $442 per night (USD)VRBO
From $659 per night (USD)Expedia
Private Heated Pool Home in Holmes Beach - Fernweh - By Island Real Estate Vaca
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Fernweh! (Means to crave for travel; being homesick for a place you've never been) New Luxury Home located at ...
From $659 per night (USD)Expedia
From $404 per night (USD)VRBO
Beautiful 3BR /2BA, Family Friendly Home w/Private pool/patio area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 bedroom 2 bathroom vacation home on beautiful Anna Maria Island, Just two short blocks from the most breathtaking whit ...
From $404 per night (USD)VRBO
From $344 per night (USD)Expedia
Changing Tides in Anna Maria
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
**ASK ABOUT LAST MINUTE DEALS! Families or groups of friends love this big open house with plenty of room and lots of a ...
From $344 per night (USD)Expedia
From $286 per night (USD)VRBO
Cozy Cottage for 4 located steps from the beach. Heated Pool in private Patio.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Yellowfin Cottage located just 2 houses from the Gulf beaches on Anna Maria Island. Yellowfin Cottage is a gr ...
From $286 per night (USD)VRBO
From $403 per night (USD)Expedia
Coastal cute on Anna Maria Island, 2 bedroom with private pool! Pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Coral Breeze (Units A and B) is your new paradise. Each 2 bedroom 2 bath side of this adorable duplex features everythin ...
From $403 per night (USD)Expedia
From $227 per night (USD)VRBO
A Wright Place 2/2 Private Pool Duplex Short Block To Beautiful Beaches
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRC16-000511 A Wright Place, located at 6803 Holmes Blvd., is a comfortable two bedroom, two bath duplex with poolside ...
From $227 per night (USD)VRBO
From $422 per night (USD)Expedia
Lakeview Cottage in Anna Maria
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Newly updated to become your favorite place to stay on the Island, Lakeview Cottage boasts a private heated pool and spa ...
From $422 per night (USD)Expedia
From $370 per night (USD)VRBO
Island Cottage with open living area, pool, ground floor very close to beach located in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Bluefin Cottage located a few houses from the Gulf beaches of Anna Maria Island. Bluefin Cottage is a half d ...
From $370 per night (USD)VRBO
From $632 per night (USD)Expedia
Beautiful Luxury Southern Style Home located in Anna Maria - Walk easily to Beach, Sleeps 6!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Southern Belle Beach House located just steps away from the Gulf beaches of Anna Maria Island. Southern Belle ...
From $632 per night (USD)Expedia
From $496 per night (USD)VRBO
3 bedroom, luxury beach house on Anna Maria Island, private pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Palm Villa welcomes you to sunny AMI! Palm Villa is a very comfortable, casual, but well-appointed Florida island getawa ...
From $496 per night (USD)VRBO
From $292 per night (USD)Expedia
Holmes Beach Cottage Steps to the Beach with Heated Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to the Starfish Shack located just a few houses from the Gulf beaches of Anna Maria Island. The Starfish Shack i ...
From $292 per night (USD)Expedia
From $246 per night (USD)VRBO
Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The cozy front porch of Gulf Winds A invites you to have your morning coffee or your evening cocktail and in the back ya ...
From $246 per night (USD)VRBO
From $668 per night (USD)Expedia
One house to the Beach with expansive heated pool!! Sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Sunset Beach House just a few steps away from the Gulf beaches of Anna Maria Island. Sunset Beach is a 4 bed ...
From $668 per night (USD)Expedia
From $273 per night (USD)VRBO
Seaside Condo – Pool & Epic Sunset Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
VRC16-000503 Seaside Beach House #102 located at 102 68th Street in Holmes Beach is a direct Gulf front complex with a ...
From $273 per night (USD)VRBO
From $301 per night (USD)Expedia
Seaside Condo – Pool & Epic Sunset Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
VRC16-000508 You will enjoy this gulf front condominium on Florida's Anna Maria Island. This is a smoke free two bedroo ...
From $301 per night (USD)Expedia
From $315 per night (USD)VRBO
Two Bedroom Cozy Island Home Right Around the Corner from Gulf Beaches. Lots of Amenities!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Loggerhead Beach House just a few houses from the Gulf beaches on Anna Maria Island. Loggerhead Beach House i ...
From $315 per night (USD)VRBO
From $370 per night (USD)Expedia
Beautiful cottage just around the corner from the beach with Private Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Seahorse Beach House located just a few houses from the Gulf beaches of Anna Maria Island. Seahorse Beach Hou ...
From $370 per night (USD)Expedia
From $381 per night (USD)VRBO
Ground Floor Cottage with 2 Master Suites and Private Heated Pool - Close to Beach!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Castaway Cottage located 2 houses down from the Gulf beaches of Anna Maria Island. Castaway Cottage is a grou ...
From $381 per night (USD)VRBO
From $345 per night (USD)Expedia
Two Bedroom Ground Floor Island Home Sleeps 5 and Includes Heated Pool.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to the Sand Dollar Shack located just a few houses from the Gulf beaches on Anna Maria Island. The Sand Dollar S ...
From $345 per night (USD)Expedia
From $341 per night (USD)VRBO
Starfish Cottage in Anna Maria
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
**ASK ABOUT LAST-MINUTE DEALS! All of the comforts of home in this tastefully designed 4-bedroom 3-bath ground floor co ...
From $341 per night (USD)VRBO
From $381 per night (USD)Expedia
Two Bedroom Cottage with Tropical Landscaping Surrounding Private Heated Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Surf Camp Cottage located just 3 houses down from the Gulf beaches of Anna Maria Island. Surf Camp Cottage is ...
From $381 per night (USD)Expedia
From $381 per night (USD)VRBO
Ground Floor home for 5, short walk to beach and private heated pool! Lovely open living area
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Citrus Cottage located steps from the Gulf beaches of Anna Maria Island. Citrus Cottage is a ground level hal ...
From $381 per night (USD)VRBO
From $414 per night (USD)Expedia
Seaside Condo – Pool & Epic Sunset Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
VRC16-000502 Seaside Beach House #101 located at 102 68th Street in Holmes Beach is a direct Gulf front complex with a ...
From $414 per night (USD)Expedia
From $501 per night (USD)VRBO
Gulf Place Unit 3 in Holmes Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! This direct Gulf-front property is sure to be a hit! It has been completely renovated re ...
From $501 per night (USD)VRBO
From $329 per night (USD)Expedia
Seaside Condo – Pool & Epic Sunset Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
VRC16-000506 You will enjoy this gulf front condominium on Florida's Anna Maria Island. This is a smoke free two-bedroo ...
From $329 per night (USD)Expedia
From $633 per night (USD)VRBO
Beautiful Island Home with Great Amenities, Pool, Grill, located close to the Gulf Beaches
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Coconut Hideaway located just steps away from the Gulf beaches of Anna Maria Island. This beach house has a p ...
From $633 per night (USD)VRBO
From $596 per night (USD)Expedia
Luxury Four Bedroom Home with Easy Access to Beach. Pool and private Patio.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Aqua Oasis located just steps from the Gulf beaches of Anna Maria Island. This beach house has a private pati ...
From $596 per night (USD)Expedia
From $325 per night (USD)VRBO
Ground Floor Two Bedroom Island Styled Home on Beautiful Anna Maria. Close to Beaches!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Groovy Gecko Cottage just a few houses down from the Gulf beaches of Anna Maria Island. This cottage is a gro ...
From $325 per night (USD)VRBO
From $378 per night (USD)Expedia
Coastal cute on Anna Maria Island, 2 bedroom with private pool! Pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Coral Breeze (Units A and B) is your new paradise. Each 2 bedroom 2 bath side of this adorable duplex features everythin ...
From $378 per night (USD)Expedia
From $640 per night (USD)VRBO
New Luxury-Professionally Decorated Home Pool/Spa 5 Minutes walk to beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This brand new rebuild on Anna Maria Island located within Anna Maria city has 3 Bedrooms, 3 Bathrooms home plus loft th ...
From $640 per night (USD)VRBO
From $694 per night (USD)Expedia
Magnolia walk to beach/shops, AMI perfect Location, private lagoon pool/spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover island paradise at Magnolia located on Magnolia Ave. , a *premier residential street* just south of Pine Ave. i ...
From $694 per night (USD)Expedia
From $508 per night (USD)VRBO
🏝 LOCAL LANDMARK. The BLUE HOUSE on PINE 🐬Casa Caliente🐬
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Newly Renovated. 🌀CASA CALIENTE 🌀 A spectacular and truly MAGICAL place to experience.🐬 AMI,fl T ...
From $508 per night (USD)VRBO
From $922 per night (USD)Expedia
Luxury AMI Home - Heated Pool & Spa - Steps to Beach - Ocean Views
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
• Custom-built 5BR/4.5BA retreat on Anna Maria Island’s quiet North Shore—just one house from the beach! • Gorgeous o ...
From $922 per night (USD)Expedia
From $407 per night (USD)VRBO
Tiki Cottage: 2.5 Blocks to Beach, Pool with Swim up Tiki Bar by Anna Maria Live Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tiki Cottage by Anna Maria Life Vacation Rentals 303 64th St, Unit B, Holmes Beach, FL 34217 What You'll Love About Thi ...
From $407 per night (USD)VRBO
From $674 per night (USD)Expedia
Glory Days: AMI North End, Backyard Oasis, Pool, 1.5 Bocks to Beach by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Glory Days by Anna Maria Life Vacation Rentals 206 Archer Way, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $674 per night (USD)Expedia
From $329 per night (USD)VRBO
Chiki Tiki West: Eclectic Beach House, Tiki Bar & Pool, 2.5 Blocks to Beach by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Chiki Tiki West by Anna Maria Life Vacation Rentals 303 64th St, Unit A, Holmes Beach, FL 34217 What You'll Love About ...
From $329 per night (USD)VRBO
From $433 per night (USD)Expedia
Escape to Anna Maria Island!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Ave Maria! We are a 5 minute walk to Anna Maria Beach. Head on down to Bean Point, located on the norther ...
From $433 per night (USD)Expedia
From $488 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 $488 per night (USD)VRBO
From $788 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 $788 per night (USD)Expedia
From $1325 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 $1325 per night (USD)VRBO
From $423 per night (USD)Expedia
Coconuts108 - GULFFRONT - 1BR/1BA with pool - By Island Real Estate Vacations
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
“The Coconuts Beach Resort 108” is a 1 bed 1 bath beach front condo, nestled in the heart of Holmes Beach. Apart of the ...
From $423 per night (USD)Expedia
From $472 per night (USD)VRBO
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 $472 per night (USD)VRBO
From $610 per night (USD)Expedia
Private Salt Water Pool & Spa, WALK TO BEACH, near Bean Point, GROUND LEVEL.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This family friendly beach house features cool tile floors, a 60" flat screen TV, complimentary WiFi and YouTubeTV and ...
From $610 per night (USD)Expedia
From $386 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 $386 per night (USD)VRBO
From $794 per night (USD)Expedia
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 $794 per night (USD)Expedia
From $2029 per night (USD)VRBO
Cloud 9 - BeachFront Splendor
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Beach Front/Heated Pool/Hot Tub/ 4 bedroom plus den North End of Anna Maria Island. Professionally decorated and fin ...
From $2029 per night (USD)VRBO
From $1318 per night (USD)Expedia
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 $1318 per night (USD)Expedia
From $1988 per night (USD)VRBO
Serendipity Deux Beachfront Retreat
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Luxury Beachfront Retreat | 4BR/4.5BA | Pool, Spa, Bikes, Kayak Escape to paradise in this 4-bedroom, 4.5-bath beachf ...
From $1988 per night (USD)VRBO
From $888 per night (USD)Expedia
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 Mari ...
From $888 per night (USD)Expedia
From $425 per night (USD)VRBO
Pool and Beach Access: Ultimate Friends Getaway! - Coconuts Gulf View #117
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coconuts Gulf View #117 by AMI Locals Condo in Holmes Beach, FL Coconuts Gulf View #117 is the ultimate spot for a fri ...
From $425 per night (USD)VRBO
From $459 per night (USD)Expedia
Charming Canal front Luxury home with brand-new Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Dockside Paradise! Dockside Paradise is a perfect canal front retreat centrally located in Anna Maria! Comp ...
From $459 per night (USD)Expedia
From $1071 per night (USD)VRBO
Amie House Mod BEACH Getaway
- 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 $1071 per night (USD)VRBO
From $379 per night (USD)VRBO
ANNA MARIA Northshore & Pine Ave LOCATION! Northshore Beach Villa
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Quaint and quiet Northshore Villa nestled in the heart of the village of Anna Maria, on Anna Maria Island. Our 2 bedroo ...
From $379 per night (USD)VRBO
From $589 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) Your Island Oasis Awaits at Sol Mate, Where Modern Comfort, ...
From $589 per night (USD)VRBO
From $770 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 $770 per night (USD)Expedia
From $623 per night (USD)VRBO
Tides Inn- Family home with tropical pool area.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Treat yourself to the relaxing getaway your family has been daydreaming about! The Tide’s Inn is a pet friendly vacation ...
From $623 per night (USD)VRBO
From $489 per night (USD)Expedia
Sorgenfrei South: Charming beach getaway across from the Gulf!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sorgenfrei South has everything you need for a perfect beach getaway. This stunning 3 bedroom, 3.5 bath home is located ...
From $489 per night (USD)Expedia
From $669 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 $669 per night (USD)VRBO
From $533 per night (USD)Expedia
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 $533 per night (USD)Expedia
From $963 per night (USD)VRBO
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 $963 per night (USD)VRBO
From $469 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 $469 per night (USD)Expedia
From $1768 per night (USD)VRBO
Felicity: Luxury Bayfront Home, Heated Pool, Hot tub and more!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Beachfront Felicity in Anna Maria Welcome to Felicity! This is one of the most exclusive homes on Anna Maria Island. Ou ...
From $1768 per night (USD)VRBO
From $499 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 $499 per night (USD)Expedia
From $494 per night (USD)VRBO
707 N Bay The Shell House - Anna Maria Island - Private home 3 Bedroom/ 2 1/2...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
707 North Bay Boulevard - The Shell House- 3 Bedroom/ 2 1/2 Bath, maximum occupancy of 6 people. Private Pool - Di ...
From $494 per night (USD)VRBO
From $503 per night (USD)Expedia
Havana Cay- Adorable cottage- only 4 houses from beach
- 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 $503 per night (USD)Expedia