Anna Maria, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Anna Maria, Florida on RentalSaver.com!

Anna Maria Rentals

From $293 per night (USD)
VRBO
Lazy Lizard! A Newly Renovated Island Cottage, Close to the Beach!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Photos Updated January 2025! LONG-TERM DISCOUNT: Stays of 4-weeks (28 nights) or more enjoy a 25% discount on the night ...
From $293 per night (USD)
VRBO
From $1116 per night (USD)
Expedia
Blue Bayou | Family fun pool home with hot tub, canalfront with a dock!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
❗ Check-in and checkout days are typically Monday or Friday—with some exceptions for holidays and certain times of the ...
From $1116 per night (USD)
Expedia
From $774 per night (USD)
VRBO
OPEN for booking after Helene & Milton! for 2025 limited dates available NOW!!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Castaway Cove, this beautiful residence is a Bean Point gem, a stunning 4 bedroom property and 2.5 bathroom o ...
From $774 per night (USD)
VRBO
From $346 per night (USD)
Expedia
Charming cottage in quiet area, close to beach & bay.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Anna Maria Island ''paradise without an attitude''. Our ground level newly renovated unit is located in t ...
From $346 per night (USD)
Expedia
From $908 per night (USD)
VRBO
Hop, Skip and a Beach - 4Bed Pool Home in Anna Maria City - By Island Real Estat
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Oh so close to the beach all it takes is a Hop, Skip and a Jump to get to the Beach! This newer 4 bedroom private pool h ...
From $908 per night (USD)
VRBO
From $1092 per night (USD)
Expedia
4 Bedroom Townhouse - Your private Holmes Beach vacation home
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to the spacious Unit 12, a four-bedroom, three-bathroom townhouse attractively adorned with white walls, cool pa ...
From $1092 per night (USD)
Expedia
From $322 per night (USD)
VRBO
AMI Moana Villa 3-minute walk to the beach plus community heated pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Find everything you need for a fun and memorable beach getaway at this three-bedroom Holmes Beach rental! You'll have a ...
From $322 per night (USD)
VRBO
From $545 per night (USD)
Expedia
Waterfront house with pool - bring boat and rod - close to Gulf and Bay Beaches
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This beautifully spacious home sits on a very large waterfront lot on the northern tip of AMI. The house is embedded in ...
From $545 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Sand Dollar Cottage - Vintage - updated - flip flop walk to Gulf Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We only rent thru VRBO! Your safety is our priority. We are writing here as the owners of this lovely cottage. If you ...
From $375 per night (USD)
VRBO
From $689 per night (USD)
Expedia
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 $689 per night (USD)
Expedia
From $268 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 $268 per night (USD)
VRBO
From $349 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 $349 per night (USD)
Expedia
From $361 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 $361 per night (USD)
VRBO
From $1208 per night (USD)
Expedia
North End AMI, Pool,Ocean Views,Tropical Oasis and elevator. No hurricane Damage
Bedrooms:
5
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 $1208 per night (USD)
Expedia
From $1519 per night (USD)
VRBO
Large Home Directly on the Beach - By Island Real Estate Vacations
Bedrooms:
4
Bathrooms:
7
Sleeps:
12
Family friendly with fantastic views and directly on the Gulf of Mexico sound like your idea of a perfect vacation renta ...
From $1519 per night (USD)
VRBO
From $1118 per night (USD)
Expedia
Private Tropical Oasis so close to BEACH with a great Pool and Spa!
Bedrooms:
6
Bathrooms:
8
Sleeps:
16
Tropical Oasis by Anna Maria Island Locals Home in Holmes Beach, FL Highlights: • Private pool with waterfall, hot tub ...
From $1118 per night (USD)
Expedia
From $1245 per night (USD)
VRBO
Home just steps to BEACH! Private pool and spa - Sign of the Mermaid
Bedrooms:
5
Bathrooms:
5
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 $1245 per night (USD)
VRBO
From $711 per night (USD)
Expedia
Mainsail Beach Inn 2 Bedroom
Bedrooms:
3
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 $711 per night (USD)
Expedia
From $689 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 $689 per night (USD)
VRBO
From $920 per night (USD)
Expedia
Jacaranda Gem by Beach Boutique Rentals
Bedrooms:
3
Bathrooms:
4
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 $920 per night (USD)
Expedia
$Ocean Walk- 5 bedroom heated pool\/spa and 6 houses from the white sandy beach$
From $1226 per night (USD)
VRBO
Ocean Walk- 5 bedroom heated pool\/spa and 6 houses from the white sandy beach
Bedrooms:
4
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 $1226 per night (USD)
VRBO
From $923 per night (USD)
Expedia
Coastal Bliss- 2-Minute Walk (500 Feet) to the beach with private pool and spa
Bedrooms:
6
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 $923 per night (USD)
Expedia
$Private Tropical Oasis - Tarpon Point - Pool\/Spa, Perfect Island Getaway!$
From $685 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 $685 per night (USD)
VRBO
From $515 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 $515 per night (USD)
Expedia
$Twin Palms: Big House Close to Beach, Heated Lagoon Pool, Infant\/Pet friendly$
From $483 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 $483 per night (USD)
VRBO
From $702 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 $702 per night (USD)
Expedia
$LOCATION, COMPLETE REHAB 1\/1. Great pool, close to beaches, twin family rooms!$
From $567 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 $567 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Pure Bliss- North End cottage with modern amenities.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 2 bedroom, 2 bathroom home certainly lives up to its name. This sweet cottage is as adorable at is it comfortable. ...
From $474 per night (USD)
Expedia
$Mermaid Cove: Updated Forida Cottage w\/pool, hot tub$
From $909 per night (USD)
VRBO
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 $909 per night (USD)
VRBO
From $1163 per night (USD)
Expedia
South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool
Bedrooms:
4
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 $1163 per night (USD)
Expedia
From $663 per night (USD)
VRBO
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 $663 per night (USD)
VRBO
From $482 per night (USD)
Expedia
Cozy Cottage w private Beach Access, AC&WiFi - NorthEnd AMI. No hurricane damage
Bedrooms:
2
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 $482 per night (USD)
Expedia
$A Wave From It All - Renovated Oasis w\/ Pool, Cabana, Putting Green & Pet Friendly$
From $721 per night (USD)
VRBO
A Wave From It All - Renovated Oasis w\/ Pool, Cabana, Putting Green & Pet Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to A Wave From It All! On Anna Maria Island (Anna Maria, FL) After sustaining hurricane damage, this charming A ...
From $721 per night (USD)
VRBO
From $1293 per night (USD)
Expedia
Incredible pool home near the beach - Take Me Away
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Take Me Away by AMI Locals Home in Holmes Beach, FL 34217 VRC20-000170 Welcome to Take Me Away, a lovely, recently reno ...
From $1293 per night (USD)
Expedia
From $1206 per night (USD)
VRBO
Yellowbird: AMI North End, Gulf Views, Pool, Tiki Hut, Elevator by Anna Maria Life Vacation Rentals
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
705 North Shore Dr., Anna Maria, FL 34216 What You'll Love About This Home: Location! North End of AMI - Quick Walk to ...
From $1206 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Bay Breeze Cottages #1 (The Mahi-Mahi)
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the ...
From $339 per night (USD)
Expedia
$⚓3\/2.5 Private Canal Front Pool Home on AMI⚓Close To Beaches$
From $254 per night (USD)
VRBO
⚓3\/2.5 Private Canal Front Pool Home on AMI⚓Close To Beaches
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Location, Location (see map): There are seven miles of pristine, quartz sand beaches shimmering along our island and you ...
From $254 per night (USD)
VRBO
From $830 per night (USD)
Expedia
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 $830 per night (USD)
Expedia
From $263 per night (USD)
VRBO
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 ...
From $263 per night (USD)
VRBO
From $2450 per night (USD)
Expedia
Spoil yourselves! Gulf front, heated pool & hot tub. NO DAMAGE! GUESTS WELCOME!
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
ANNA MARIA IS OPEN: OUR BEACHES, SHOPS AND RESTAURANTS. JOIN OUR GUESTS DRIVING GOLF CARTS, COLLECTING SHELLS AND RIDING ...
From $2450 per night (USD)
Expedia
From $579 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 $579 per night (USD)
VRBO
From $776 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 $776 per night (USD)
Expedia
$Beautiful 3BR \/2BA, Family Friendly Home w\/Private pool\/patio area$
From $345 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 $345 per night (USD)
VRBO
From $492 per night (USD)
Expedia
HEATED POOL & SPA ON CANAL, FREE WiFi & Trolley, Close to Beach & Bay!
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 a ...
From $492 per night (USD)
Expedia
Click For Pricing
VRBO
Two bedroom private heated pool and hot tub, on AMI- pet friendly!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Island Delight is a cozy 2 bedroom one bath duplex with a private heated saltwater pool and hot tub in the Seaside Garde ...
Click For Pricing
VRBO
From $408 per night (USD)
Expedia
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 $408 per night (USD)
Expedia
From $448 per night (USD)
VRBO
Coastal cute on Anna Maria Island, 2 bedroom with private pool! Pet friendly
Bedrooms:
2
Bathrooms:
4
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 $448 per night (USD)
VRBO
$A Wright Place 2\/2 Private Pool Duplex Short Block To Beautiful Beaches$
From $312 per night (USD)
Expedia
A Wright Place 2\/2 Private Pool Duplex Short Block To Beautiful Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VRC16-000511 A Wright Place, located at 6803 Holmes Blvd., is a comfortable two bedroom, two bath duplex with poolside ...
From $312 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Heated Pool & Spa, FREE WiFi, Near AMI Beach & Village, Dog* (See Note)...
Bedrooms:
2
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 $436 per night (USD)
VRBO
From $445 per night (USD)
Expedia
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 $445 per night (USD)
Expedia
From $895 per night (USD)
VRBO
Beautiful Luxury Southern Style Home located in Anna Maria - Walk easily to Beach, Sleeps 6!
Bedrooms:
5
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 $895 per night (USD)
VRBO
From $569 per night (USD)
Expedia
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 $569 per night (USD)
Expedia
From $439 per night (USD)
VRBO
Holmes Beach Cottage Steps to the Beach with Heated Pool!
Bedrooms:
2
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 $439 per night (USD)
VRBO
From $268 per night (USD)
Expedia
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 $268 per night (USD)
Expedia
From $1086 per night (USD)
VRBO
One house to the Beach with expansive heated pool!! Sleeps 8
Bedrooms:
5
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 $1086 per night (USD)
VRBO
Click For Pricing
Expedia
Updated 2 bedroom, beach condo on Anna Maria Island!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This is a bright and well maintained two bedroom/ two bath condo in desirable Westbay Pointe & Moorings Condominiums sit ...
Click For Pricing
Expedia
From $380 per night (USD)
VRBO
Seaside Beach House 102 Gulf Front Condo Pool Unforgettable Sunset Views
Bedrooms:
2
Bathrooms:
2
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 $380 per night (USD)
VRBO
From $531 per night (USD)
Expedia
Seaside Beach House 205 Gulf Front Condo Pool Unforgettable Sunset Views
Bedrooms:
2
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 $531 per night (USD)
Expedia
From $430 per night (USD)
VRBO
Two Bedroom Cozy Island Home Right Around the Corner from Gulf Beaches. Lots of Amenities!
Bedrooms:
2
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 $430 per night (USD)
VRBO
From $430 per night (USD)
Expedia
Beautiful cottage just around the corner from the beach with Private Pool!
Bedrooms:
2
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 $430 per night (USD)
Expedia
From $367 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 $367 per night (USD)
VRBO
From $434 per night (USD)
Expedia
Two Bedroom Ground Floor Island Home Sleeps 5 and Includes Heated Pool.
Bedrooms:
2
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 $434 per night (USD)
Expedia
Click For Pricing
VRBO
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
**ASK ABOUT LAST MINUTE DEALS! This absolutely charming cottage can be yours for an affordable vacation in ...
Click For Pricing
VRBO
$CHARMING COTTAGE W\/HEATED POOL, Close to Gulf & Bay Beach, FREE WiFi\/Trolley,...$
From $556 per night (USD)
Expedia
CHARMING COTTAGE W\/HEATED POOL, Close to Gulf & Bay Beach, FREE WiFi\/Trolley,...
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 gro ...
From $556 per night (USD)
Expedia
From $409 per night (USD)
VRBO
Two Bedroom Cottage with Tropical Landscaping Surrounding Private Heated Pool!
Bedrooms:
2
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 $409 per night (USD)
VRBO
From $435 per night (USD)
Expedia
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 $435 per night (USD)
Expedia
From $387 per night (USD)
VRBO
Seaside Beach House 101 Gulf Front Condo Pool Unforgettable 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 $387 per night (USD)
VRBO
$GULF BEACH WALK OUT 3 BED\/2 BATH, Heated Pool, FREE WiFi & Trolley, A Rare...$
From $711 per night (USD)
Expedia
GULF BEACH WALK OUT 3 BED\/2 BATH, Heated Pool, FREE WiFi & Trolley, A Rare...
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 ...
From $711 per night (USD)
Expedia
From $496 per night (USD)
VRBO
Seaside Beach House 105 Gulf Front Condo Pool Unforgettable Sunset Views
Bedrooms:
2
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 $496 per night (USD)
VRBO
From $1040 per night (USD)
Expedia
Beautiful Island Home with Great Amenities, Pool, Grill, located close to the Gulf Beaches
Bedrooms:
5
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 $1040 per night (USD)
Expedia
From $1040 per night (USD)
VRBO
Luxury Four Bedroom Home with Easy Access to Beach. Pool and private Patio.
Bedrooms:
5
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 $1040 per night (USD)
VRBO
From $421 per night (USD)
Expedia
Ground Floor Two Bedroom Island Styled Home on Beautiful Anna Maria. Close to Beaches!!
Bedrooms:
2
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 $421 per night (USD)
Expedia
From $448 per night (USD)
VRBO
Coastal cute on Anna Maria Island, 2 bedroom with private pool! Pet friendly
Bedrooms:
2
Bathrooms:
4
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 $448 per night (USD)
VRBO
From $897 per night (USD)
Expedia
Anna Maria Escape Beach Front and Close to Bean Point
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Anna Maria Escape located at 725 North Shore Drive in Anna Maria city is just that - a peaceful, relaxed place to ge ...
From $897 per night (USD)
Expedia
$New Luxury-Professionally Decorated Home Pool\/Spa 5 Minutes walk to beach$
From $871 per night (USD)
VRBO
New Luxury-Professionally Decorated Home Pool\/Spa 5 Minutes walk to beach
Bedrooms:
3
Bathrooms:
4
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 $871 per night (USD)
VRBO
$Magnolia walk to beach\/shops, AMI perfect Location, private lagoon pool\/spa$
From $846 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 $846 per night (USD)
Expedia
$Sweet N Salty - 25% off 8\/10 - 9\/14 - Pool & Spa - Walking distance to Pine Ave$
From $660 per night (USD)
VRBO
Sweet N Salty - 25% off 8\/10 - 9\/14 - Pool & Spa - Walking distance to Pine Ave
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
210 Crescent Drive is a colorful, bright and airy 2 bedroom and 2 bathroom elevated home located on the north end of Ann ...
From $660 per night (USD)
VRBO
From $563 per night (USD)
Expedia
🏝 LOCAL LANDMARK. The BLUE HOUSE on PINE 🐬Casa Calienta🐬
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly Renovated. 🌀CASA CALIENTE 🌀 A spectacular and truly MAGICAL place to experience.🐬 AMI,fl T ...
From $563 per night (USD)
Expedia
From $543 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:
4
Sleeps:
6
Tiki Cottage by Anna Maria Life Vacation Rentals 303 64th St, Unit B, Holmes Beach, FL 34217 2.5 Blocks to the Beach! ...
From $543 per night (USD)
VRBO
From $973 per night (USD)
Expedia
Glory Days: AMI North End, Backyard Oasis, Pool, 1.5 Bocks to Beach by Anna Maria Life
Bedrooms:
2
Bathrooms:
4
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 $973 per night (USD)
Expedia
From $434 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 $434 per night (USD)
VRBO
From $437 per night (USD)
Expedia
Escape to an island adventure!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Ave Maria! This desirable north island location is a gem boasting a short walk to the beach, bay, with shopp ...
From $437 per night (USD)
Expedia
From $493 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 $493 per night (USD)
VRBO
$Aloha Beaches! Newly Renovated 4 Bedroom 3 Bath Home w\/ Private Pool!$
From $803 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 $803 per night (USD)
Expedia
From $1703 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 $1703 per night (USD)
VRBO
$Coconuts108 - GULFFRONT - 1BR\/1BA with pool - By Island Real Estate Vacations$
From $441 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 $441 per night (USD)
Expedia
From $514 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 $514 per night (USD)
VRBO
From $658 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 $658 per night (USD)
Expedia
From $417 per night (USD)
VRBO
Chapter 2: Renovated pool home, tiki hut and close to beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to Chapter 2 Create some magic memories in a slice of “Old Florida”. Relax outside in the heated saltwater p ...
From $417 per night (USD)
VRBO
From $1065 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 WITH A CHECK-IN DATE AFTER SEPTEMBER 23, 2023! All Drivers must be o ...
From $1065 per night (USD)
Expedia
$Cloud 9- beachfront\/heated pool\/ 4 plus bedroom$
From $2619 per night (USD)
VRBO
Cloud 9- beachfront\/heated pool\/ 4 plus bedroom
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
Beach Front/Heated Pool/Hot Tub/ 4 bedroom plus den Located on the North End of Anna Maria Island. Professionally decora ...
From $2619 per night (USD)
VRBO
From $1625 per night (USD)
Expedia
Big Family Beach House: Large family home, heated pool, putting green
Bedrooms:
6
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 $1625 per night (USD)
Expedia
$luxury beachfront\/ heated pool$
From $2281 per night (USD)
VRBO
luxury beachfront\/ heated pool
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
4 bedroom 4.5 bath Beach Front Home with a Beach Front Heated Pool and Spa,Gourmet Kitchen, high end finishes and one o ...
From $2281 per night (USD)
VRBO
$Oceans Blue Walk to the beach,stunning pool\/spa private dock great location$
From $899 per night (USD)
Expedia
Oceans Blue Walk to the beach,stunning pool\/spa private dock great location
Bedrooms:
4
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 $899 per night (USD)
Expedia
From $1039 per night (USD)
VRBO
Pool and Beach Access: Ultimate Friends Getaway! - Coconuts Gulf View #117
Bedrooms:
2
Bathrooms:
3
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 $1039 per night (USD)
VRBO
From $650 per night (USD)
Expedia
Charming Canal front Luxury home with brand-new Pool!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to Dockside Paradise! Dockside Paradise is a perfect canal front retreat centrally located in Anna Maria! Comp ...
From $650 per night (USD)
Expedia
From $1171 per night (USD)
VRBO
RECOVERED FROM STORMS Amie House Mod BEACH Getaway
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
***HURRICANE RECOVERY: BEACH BLISS AWAITS!*** This house is in perfect shape for your getaway—restaurants and shops are ...
From $1171 per night (USD)
VRBO
From $354 per night (USD)
Expedia
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 $354 per night (USD)
Expedia
$Sol Mate – Updated 3BR Home w\/ Heated Pool, Spa, Walk to Bean Point Beach & Pine Ave, Pet-Friendly$
From $665 per night (USD)
VRBO
Sol Mate – Updated 3BR Home w\/ Heated Pool, Spa, Walk to Bean Point Beach & Pine Ave, Pet-Friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Sol Mate! On Anna Maria Island (Anna Maria, FL) Bright and Beautifully Updated 3-Bedroom Home with Heated Po ...
From $665 per night (USD)
VRBO
From $898 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 $898 per night (USD)
Expedia

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