Anna Maria Rentals
- From $508 per night (USD)
VRBO
A Mermaid's Tale - By Island Real Estate Vacations
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
When you arrive at Anna Maria Island vacation rental home “A Mermaid's Tale” you are greeted with true island style and ...
From $508 per night (USD)VRBO
- From $522 per night (USD)
Expedia
Marias Way - 3BR\/2BA Pool Home - Anna Maria City -By Island Real Estate Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
BRAND NEW POOL! Located on the coveted northern end of Anna Maria Island, “Maria's Way” is a charming beach cottage off ...
From $522 per night (USD)Expedia
- From $874 per night (USD)
VRBO
One block off Pine Ave w\/ Amazing Rooftop Views! - AMI Memories
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
AMI Memories by AMI Locals Home in Anna Maria VR20-000052 Welcome to AMI Memories! This three-level home boasts fiv ...
From $874 per night (USD)VRBO
- From $1150 per night (USD)
VRBO
Stunning new 4 bedroom 4.5 bath home with heated pool\/spa and views of Tampa Bay
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Marina Magic is a brand new bay view home available for rent for the very first time. Tucked among swaying palm trees o ...
From $1150 per night (USD)VRBO
- From $591 per night (USD)
VRBO
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 $591 per night (USD)VRBO
- From $575 per night (USD)
Expedia
Bean Point Gem awaits your stay!
- 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 $575 per night (USD)Expedia
- From $254 per night (USD)
VRBO
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 $254 per night (USD)VRBO
- From $709 per night (USD)
Expedia
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 $709 per night (USD)Expedia
- From $500 per night (USD)
VRBO
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 $500 per night (USD)VRBO
- From $300 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 $300 per night (USD)VRBO
- From $474 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
773 Jacaranda Rd., Anna Maria, FL 34216 What You'll Love About This Home: Location! Just two blocks from the North En ...
From $474 per night (USD)VRBO
- From $899 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
216 Chilson Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! North End of AMI - 2 Blocks to the B ...
From $899 per night (USD)Expedia
- From $225 per night (USD)
VRBO
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 $225 per night (USD)VRBO
- From $999 per night (USD)
VRBO
North End of AMI, Heated\/Chilled Pool, Ocean Views, Tropical Oasis with elevator
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
This home is a showcase stunner! Sea Breeze was has been remodeled and professionally decorated. It is located at the q ...
From $999 per night (USD)VRBO
- From $891 per night (USD)
VRBO
Large Home Directly on the Beach - By Island Real Estate Vacations
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Family friendly with fantastic views and directly on the Gulf of Mexico sound like your idea of a perfect vacation renta ...
From $891 per night (USD)VRBO
- From $1355 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 $1355 per night (USD)Expedia
- From $510 per night (USD)
VRBO
Escape the ordinary to this Luxury home with Pool and Spa! Just steps to BEACH!
- Bedrooms:
- 5
- 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 f ...
From $510 per night (USD)VRBO
- From $760 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 $760 per night (USD)Expedia
- From $714 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 $714 per night (USD)VRBO
- From $652 per night (USD)
VRBO
Jacaranda Gem by Beach Boutique Rentals
- Bedrooms:
- 3
- 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 $652 per night (USD)VRBO
- From $625 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 $625 per night (USD)VRBO
- From $636 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 $636 per night (USD)Expedia
- From $644 per night (USD)
VRBO
Spoonbill Hideaway-Huge Pool and Spa across from Gulf Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our house is located on North Shore Drive in Anna Maria Florida across the street from one of the widest and finest beac ...
From $644 per night (USD)VRBO
- From $732 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 $732 per night (USD)VRBO
- From $364 per night (USD)
VRBO
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 $364 per night (USD)VRBO
- From $775 per night (USD)
Expedia
Big Family 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 tech husband! Pet friendly, lots of space and charm, gre ...
From $775 per night (USD)Expedia
- Click For Pricing
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 ...
Click For PricingExpedia
- From $495 per night (USD)
VRBO
LOCATION, LOCATION, LOCATION. Great pool, close to beaches, twin family rooms!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Location, Location, Location.... recently remodeled, surrounded by multi million dollar homes.....and three great beache ...
From $495 per night (USD)VRBO
- From $526 per night (USD)
VRBO
The Salted Coconut by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
THE SALTED COCONUT The Salted Coconut is just a short stroll to the beautiful beaches of Anna Maria! This g ...
From $526 per night (USD)VRBO
- From $418 per night (USD)
Expedia
Pure Bliss- North End cottage with modern amenities.
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $418 per night (USD)Expedia
- From $646 per night (USD)
VRBO
Updated, Charming Florida Cottage
- 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 $646 per night (USD)VRBO
- From $1213 per night (USD)
Expedia
South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
"Remember the first time you fell in love? Prepare for the butterflies again! We are delighted to present the South Bay ...
From $1213 per night (USD)Expedia
- From $497 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 $497 per night (USD)VRBO
- From $390 per night (USD)
VRBO
Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This charming Sea Garden Cottage is a true island gem and escape. Sea Garden Cottage is located on North Shore Drive at ...
From $390 per night (USD)VRBO
- From $595 per night (USD)
VRBO
A Wave From It All - New Luxury Renovated Home! Heated Pool, Cabana, Hammock, Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to A Wave From It All! On Anna Maria Island (Anna Maria, FL) HIGHLIGHTS: - Open layout and spacious Kitchen, Di ...
From $595 per night (USD)VRBO
- From $1250 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 $1250 per night (USD)Expedia
- From $769 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 $769 per night (USD)VRBO
- From $399 per night (USD)
Expedia
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 $399 per night (USD)Expedia
- From $202 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 $202 per night (USD)VRBO
- From $564 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
125 Crescent Drive, Anna Maria, FL 34216 What You'll Love About This Home: Location! AMI North End Canal Home! 3 Block ...
From $564 per night (USD)Expedia
- From $202 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
606 N. Shore Drive, #4, Anna Maria, FL 34216 What You'll Love About This Home: Location! North End AMI Canal Home! Ste ...
From $202 per night (USD)VRBO
- From $325 per night (USD)
Expedia
Summer Breeze: North End, Dog Friendly, Kayaks, on Canal by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
606 N. Shore, Unit 0, Anna Maria, FL 34216 What You'll Love About This Home: Location! North End AMI Canal Home! Steps ...
From $325 per night (USD)Expedia
- From $2134 per night (USD)
VRBO
NEST ON THE BEACH IS MAGICAL Heated pool, hot tub, 5 master suites Sunset views!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
SPOIL YOURSELVES ON THE GULF OF MEXICO BEACH! Let’s talk Beach House? Whether you're building sand castles with the lit ...
From $2134 per night (USD)VRBO
- From $451 per night (USD)
Expedia
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 $451 per night (USD)Expedia
- From $205 per night (USD)
VRBO
Osprey in Blue Lagoon - 2BR Condo with Pool - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Blue Lagoon is a small upscale 6 unit complex and this holiday rentals is just a short stroll from the best beaches ...
From $205 per night (USD)VRBO
- From $424 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 $424 per night (USD)Expedia
- From $376 per night (USD)
VRBO
Seascapes by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on the far North end of Anna Maria right at Bean Point, is Seascapes, newly remodeled three- bedroom, two-bathro ...
From $376 per night (USD)VRBO
- From $371 per night (USD)
Expedia
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 $371 per night (USD)Expedia
- From $328 per night (USD)
VRBO
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 $328 per night (USD)VRBO
- From $258 per night (USD)
Expedia
Two bedroom private heated pool, on Anna Maria Island - pet friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Island Delight is a cozy 2 bedroom one bath half-duplex with a private heated saltwater pool in the Seaside Gardens neig ...
From $258 per night (USD)Expedia
- From $294 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 $294 per night (USD)VRBO
- From $315 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 $315 per night (USD)Expedia
- From $249 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 $249 per night (USD)VRBO
- From $299 per night (USD)
Expedia
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 $299 per night (USD)Expedia
- From $336 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 $336 per night (USD)VRBO
- From $479 per night (USD)
Expedia
Lake By The Beach Pool\/Spa Home Overlooking Secluded Lake Native Landscaping
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
VRC16-000495 The Lake by the Beach at 6806 Palm Drive offers the best of both worlds! This beautiful two bedroom, two b ...
From $479 per night (USD)Expedia
- From $815 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 $815 per night (USD)VRBO
- From $415 per night (USD)
Expedia
3 bedroom, luxury beach house on Anna Maria Island, private pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Palm Villa is a New England style cottage and Florida Keys getaway all rolled into one. The vaulted main room ceiling gi ...
From $415 per night (USD)Expedia
- From $320 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 $320 per night (USD)VRBO
- From $452 per night (USD)
Expedia
Three Bedroom Ground Floor Home with Retro Finishes and many Amenities!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Lime Cottage located just 2 blocks from the Gulf beaches of Anna Maria Island. Lime Cottage is a ground level ...
From $452 per night (USD)Expedia
- From $202 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 $202 per night (USD)VRBO
- From $647 per night (USD)
Expedia
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 $647 per night (USD)Expedia
- From $371 per night (USD)
VRBO
SPECTACULAR 3 BED\/2BATH w\/Heated Pool & Spa FREE WiFi & Trolley, Close to...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! "Sea La Vie" is the Island getaway you have been searching for. You and your ...
From $371 per night (USD)VRBO
- From $385 per night (USD)
Expedia
Heated Pool FREE WiFi, Close to Beach Dock your Boat Dog* (See Note) Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
**ASK ABOUT LAST MINUTE DEALS! You and your family will love staying in this beautiful three-bedroom, three ...
From $385 per night (USD)Expedia
- From $145 per night (USD)
VRBO
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 ...
From $145 per night (USD)VRBO
- From $330 per night (USD)
Expedia
Seaside Beach House 102 Gulf Front Condo Pool Unforgettable Sunset Views
- Bedrooms:
- 2
- 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 $330 per night (USD)Expedia
- From $482 per night (USD)
VRBO
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 $482 per night (USD)VRBO
- From $260 per night (USD)
Expedia
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 $260 per night (USD)Expedia
- Click For Pricing
VRBO
Anna Maria Island Beach Condo w\/ Stunning Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your ultimate Sunshine State getaway starts here at this 2-bedroom, 2-bath Holmes Beach vacation rental, situated right ...
Click For PricingVRBO
- From $320 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 $320 per night (USD)Expedia
- From $347 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 $347 per night (USD)VRBO
- From $299 per night (USD)
Expedia
Cute Cottage with 2 Master Suites and Expansive Pool Two Blocks from Beautiful Anna Maria Beaches!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Lemon Cottage located just 2 blocks from the Gulf beaches of Anna Maria Island. Lemon Cottage is a ground lev ...
From $299 per night (USD)Expedia
- From $320 per night (USD)
VRBO
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 $320 per night (USD)VRBO
- From $171 per night (USD)
Expedia
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 ...
From $171 per night (USD)Expedia
- From $356 per night (USD)
VRBO
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 $356 per night (USD)VRBO
- From $326 per night (USD)
Expedia
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 $326 per night (USD)Expedia
- From $347 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 $347 per night (USD)VRBO
- From $508 per night (USD)
Expedia
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 $508 per night (USD)Expedia
- From $439 per night (USD)
VRBO
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 $439 per night (USD)VRBO
- From $481 per night (USD)
Expedia
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 $481 per night (USD)Expedia
- From $846 per night (USD)
VRBO
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 $846 per night (USD)VRBO
- From $700 per night (USD)
Expedia
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 $700 per night (USD)Expedia
- From $320 per night (USD)
VRBO
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 $320 per night (USD)VRBO
- From $315 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 $315 per night (USD)Expedia
- From $445 per night (USD)
VRBO
90sec walk to beach, quiet, sunny pool, clean, 500mb, solar system, PS4
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We have developed a comprehensive Safety / Cleaning / Sanitation Plan and work with an amazing team to ensure the home & ...
From $445 per night (USD)VRBO
- From $693 per night (USD)
Expedia
Anna Maria Escape Beach Front and Close to Bean Point
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $693 per night (USD)Expedia
- From $678 per night (USD)
VRBO
Beach Front and Close to Bean Point Azure Seas
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Azure Seas is thoroughly cleaned and sanitized prior to your arrival. We pay special attention to high touch areas like ...
From $678 per night (USD)VRBO
- From $599 per night (USD)
Expedia
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 $599 per night (USD)Expedia
- From $529 per night (USD)
VRBO
Magnolia in Anna Maria, FL
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Rates have been reduced 20% from 1/6/24 to 2/9/24, book now!! *3 Night Minimum stays are allowed during low ...
From $529 per night (USD)VRBO
- From $538 per night (USD)
Expedia
Sweety N Salty- Brand new pool and 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 $538 per night (USD)Expedia
- From $627 per night (USD)
VRBO
🏝AMI’s local LANDMARK🏖<br> The BLUE HOUSE on PINE <br> 🐬Casa Calienta🐬
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
🌀CASA CALIENTE 🌀 A spectacular and truly MAGICAL place to experience.🐬 AMI,fl This 2 bed , 2 bath home is a specta ...
From $627 per night (USD)VRBO
- From $780 per night (USD)
VRBO
Anna Maria Heated Pool Ocean View Hot Tub Short Walk To Beach
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Palm Beach at AMI. This custom built, 5 Bedroom 4.5 Bath, home with Heated Pool and Spa will make you feel re ...
From $780 per night (USD)VRBO
- From $339 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 2.5 Blocks to the Beach! ...
From $339 per night (USD)VRBO
- From $581 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
206 Archer Way, Anna Maria, FL 34216 What You'll Love About This Home: Location! 1.25 Blocks to the Beach! 3 Bedrooms / ...
From $581 per night (USD)Expedia
- From $499 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
303 64th St, Unit A, Holmes Beach, FL 34217 What You'll Love About This Home: Location! 2.5 Blocks to the Beach! 3 Bed ...
From $499 per night (USD)VRBO
- From $315 per night (USD)
Expedia
Escape to an island adventure!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Ave Maria! This north end gem boasts a central Anna Maria location with an easy walk to the beach, shopping, ...
From $315 per night (USD)Expedia
- From $415 per night (USD)
VRBO
Preferred AMI Spot, Beach-Rod&Reel Pier Across Street! Newly back on VRBO.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
THIS IS THE BEST LOCATION AND BEST PRICE FOR LOCATION, COMFORT, AND CONVENIENCE. Enjoy our remodeled and comfortable is ...
From $415 per night (USD)VRBO
- From $575 per night (USD)
Expedia
Memories are Made in Flip Flops
- 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 $575 per night (USD)Expedia
- From $625 per night (USD)
VRBO
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 $625 per night (USD)VRBO
- From $1283 per night (USD)
Expedia
Dolphin Tales: Pool, Bay Views & Private Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
836 S Bay Blvd, Anna Maria, FL 34216 What You'll Love About This Home: Location! Stunning Views with Private Access to ...
From $1283 per night (USD)Expedia