Anna Maria Rentals
- From $323 per night (USD)
VRBO
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 $323 per night (USD)VRBO
- From $439 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 $439 per night (USD)VRBO
- From $581 per night (USD)
VRBO
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 $581 per night (USD)VRBO
- From $357 per night (USD)
Expedia
Chapter 2: Newly renovated pool home, tiki hut and close to beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Chapter II Create some magic memories in a slice of “Old Florida”. Relax outside in the heated saltwater ...
From $357 per night (USD)Expedia
- From $879 per night (USD)
VRBO
Golf Cart included! Luxurious Outdoor Living w\/ Putting Green, Outdoor Kitchen
- 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 $879 per night (USD)VRBO
- From $2529 per night (USD)
Expedia
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 $2529 per night (USD)Expedia
- From $1396 per night (USD)
VRBO
Big Family Beach House
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Big Family Beach House Coastal elegance describes this spectacular large family home. It's located in the heart of Anna ...
From $1396 per night (USD)VRBO
- From $1767 per night (USD)
Expedia
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 $1767 per night (USD)Expedia
- From $1121 per night (USD)
VRBO
Discounts for Super Bowl. Heated Pool, Internet, 4 Bed 3 Bath. On Historic Pine
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
This 4 bedroom/3 bath home is situated in the perfect location on the historical and the most sought after street on Ann ...
From $1121 per night (USD)VRBO
- From $637 per night (USD)
Expedia
Oceans Blue in Anna Maria
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
*3 Night Minimum stays are allowed during low season, please refer to the rate table for the specific date ranges* ...
From $637 per night (USD)Expedia
- From $325 per night (USD)
VRBO
Enjoy pool and beach views! Perfect location on AMI!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coconuts Gulf View #117 by AMI Locals Condo in Holmes Beach, FL Highlights: • Private Lanai with direct beach and pool ...
From $325 per night (USD)VRBO
- From $545 per night (USD)
Expedia
Charming Canal front Luxury home with brand-new Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Dockside Paradise by AMI Locals Home in Anna Maria, FL Features: • Canal front home • private pool • close to Pine Aven ...
From $545 per night (USD)Expedia
- From $1141 per night (USD)
VRBO
Amie House Chef’s kitchen, 2 King suites walk to beach\/Stunning Pool
- Bedrooms:
- 5
- 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 $1141 per night (USD)VRBO
- From $258 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 $258 per night (USD)VRBO
- From $1272 per night (USD)
VRBO
SunKissed Cottage - beachfront north end AMI
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Beachfront, North End, large 2 bedroom with expansive views of the dolphins frolicking in the azure waters of the North ...
From $1272 per night (USD)VRBO
- From $492 per night (USD)
Expedia
Rose Quartz: Discover Bliss! A Family Retreat with Heated Pool & Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Rose Quartz, your haven of warmth and comfort nestled in the heart of Anna Maria Island. Step inside, and you ...
From $492 per night (USD)Expedia
- From $595 per night (USD)
VRBO
Found Your Sol Mate! Gorgeous Home w\/ Pool, Spa, Steps to Bean Point, Dogs OK!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Sol Mate! On Anna Maria Island (Anna Maria, FL) Beautifully updated, fresh, and clean elevated 3 Bed, 2.5 Ba ...
From $595 per night (USD)VRBO
- From $243 per night (USD)
Expedia
313 Palm Ave in Anna Maria
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
313 Palm Avenue - Anna Maria Island - Duplex - 2 Bedroom /1 Bathroom, maximum occupancy of 4 people. No Pool - Dis ...
From $243 per night (USD)Expedia
- From $285 per night (USD)
VRBO
Emerald Shores East: Steps to the beach, shared pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come enjoy a cozy duplex on one of Anna Maria Island’s tranquil family beaches. Emerald Shores East is one of two unit ...
From $285 per night (USD)VRBO
- From $712 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 $712 per night (USD)Expedia
- Click For Pricing
VRBO
Amazing Resort Sixty-Six, Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigned ...
Click For PricingVRBO
- Click For Pricing
VRBO
The Jersey Girl: Split house, one block from Pine Ave and short walk to Bay
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
The Jersey Girl House and Cottage is a stunning property that will not disappoint. With 3 bedrooms and 2 baths in the ma ...
Click For PricingVRBO
- From $764 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 premium pet friendly ...
From $764 per night (USD)VRBO
- From $501 per night (USD)
Expedia
Sorgenfrei South: Charming beach getaway across from the Gulf!
- Bedrooms:
- 4
- 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 $501 per night (USD)Expedia
- From $468 per night (USD)
VRBO
Kingfish: *Canalfront *Paddleboards *Putt Putt *Heated Pool *Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
You want WARMTH –You want SUN – You NEED BEACH – KINGFISH is just the thing! Escape to one of Anna Maria Island’s most ...
From $468 per night (USD)VRBO
- From $393 per night (USD)
Expedia
Beachy Keen 408 in Anna Maria
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beachy Keen 408 - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. Private Pool - Distance to ...
From $393 per night (USD)Expedia
- From $588 per night (USD)
VRBO
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 Island, FL 34216 AT A GLANCE Newly remodeled professionally decorated ...
From $588 per night (USD)VRBO
- From $793 per night (USD)
Expedia
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 $793 per night (USD)Expedia
- From $235 per night (USD)
VRBO
Emerald Shores West: Steps to the beach, shared pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come enjoy a cozy duplex on one of Anna Maria Island’s tranquil family beaches. Emerald Shores West is one of two unit ...
From $235 per night (USD)VRBO
- From $464 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 $464 per night (USD)Expedia
- From $1428 per night (USD)
VRBO
Bay Breeze: 4 BR, 4.5 BA House in Anna Maria, Sleeps 8
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Beachfront Bay Breeze in Anna Maria Welcome to Bay Breeze! This is one of the most exclusive homes on Anna Maria Island ...
From $1428 per night (USD)VRBO
- From $396 per night (USD)
Expedia
Lovin' the Sannd: 3 BR, 3 BA House in Anna Maria, Sleeps 7
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
If you're looking to escape the hustle and bustle of everyday life, look no further than "Lovin' the SANND". This three ...
From $396 per night (USD)Expedia
- From $450 per night (USD)
VRBO
707 N Bay The Shell House
- Bedrooms:
- 3
- 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 $450 per night (USD)VRBO
- From $425 per night (USD)
Expedia
Havana Cay- Adorable cottage- only 4 houses from beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
At a Glance Historic 1924 Latin style home with deluxe renovations Only 4 houses in from the beach- a 30 second walk to ...
From $425 per night (USD)Expedia
- From $240 per night (USD)
VRBO
Newly updated 2 bedroom condo on the beach block!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Kitchen and Dining area, Living Room, Private Lanai with beach and pool views The view from this condo is absolutely fa ...
From $240 per night (USD)VRBO
- From $837 per night (USD)
Expedia
Stunning new luxury home, pool + spa, walk to the beach! Summer awaits!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 8
Oar House by AMI Locals Home in Anna Maria, FL Located in the most desired North End of Anna Maria Highlights: - Ne ...
From $837 per night (USD)Expedia
- From $299 per night (USD)
VRBO
A Shore Thing - Relaxing Island Living , Large Heated Pool, Boat Lift
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beach house is "A Shore Thing" for creating fantastic vacation memories. This newly furnished ground level home is ...
From $299 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Anna Marie Hideaway!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
2013 is the first year we have rented our family beach house on Anna Maria Island. Our kids are in school and it is hard ...
From $550 per night (USD)VRBO
- From $495 per night (USD)
VRBO
Comfortable and just-updated 1 bedroom beachfront condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Coconuts Beachfront #110! Highlights: -Newly remodeled with updated furniture and decor -Large bay of window ...
From $495 per night (USD)VRBO
- From $488 per night (USD)
VRBO
Bliss by the Beach by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy beachside bliss in this luxury home on the secluded and desirable North end of Anna Maria near Bean Point! *Featu ...
From $488 per night (USD)VRBO
- From $1296 per night (USD)
VRBO
Gorgeous canal front luxury home, pool, spa and rooftop deck!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 8
Sail Away by AMI Locals Home in Anna Maria, FL Less than a 5-minute walk from the pristine Gulf beaches Highlights: - ...
From $1296 per night (USD)VRBO
- From $298 per night (USD)
Expedia
Mermaids and Manatees:North End, On Canal, Pool, Dog Friendly by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
101 Gull Dr., Anna Maria, FL 34216 What You'll Love About This Home: Location! Nestled on the North End of the Island. ...
From $298 per night (USD)Expedia
- From $393 per night (USD)
VRBO
Lakeside Beach House 3\/2 Pool Home Outdoor Kitchen Close to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VRC16-000807 The Lakeside Beach House is a wonderful newly renovated three bedroom, two bath home with a private heated ...
From $393 per night (USD)VRBO
- From $328 per night (USD)
Expedia
Stunning 3Bed\/3 Bath, Heated Pool, FREE WiFi, Close to Beach, On Canal to...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**ASK ABOUT LAST MINUTE DEALS! Welcome to paradise at Pelican Point! This stunning 3 bedroom/3 bath home h ...
From $328 per night (USD)Expedia
- From $388 per night (USD)
VRBO
Relaxing Home with Private Pool, High-Speed WiFi, Central AC, & Washer\/Dryer
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Southern Magnolia Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $388 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Luxury Beach Cottage for Families on the North Shore of Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beach chic meets casual elegance in this brand new ground level cottage only steps away from the best beach on Anna Mari ...
From $600 per night (USD)VRBO
- From $1142 per night (USD)
VRBO
⚓Bay Dreamin! Walk to the Beach, Pier, & Pine Ave! Heated Pool!⚓⛳🏖🌅
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Have you been dreaming about the water here on Floridas Beautiful Gulf Coast? Well, come enjoy "Bay Dreamin" *Construc ...
From $1142 per night (USD)VRBO
- From $1304 per night (USD)
Expedia
Sea La Vie AM: Bay front, pool, hot tub, rooftop deck, and water sports gear!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
HGTV Beach Hunters Renovated Beach Front Home with a heated pool and 3 bedrooms. 1 Paddle boards & 2 kayak included. ...
From $1304 per night (USD)Expedia
- Click For Pricing
Expedia
Newly constructed home with gorgeous bay views and rooftop deck!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • One-minute walk to the Bay • Private pool • Putting green • Rooftop deck • Dog friendly with host approval ...
Click For PricingExpedia
- From $585 per night (USD)
Expedia
Beach Bay Serenity: Pine Ave canal front pool home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Beach Bay Serenity! This gorgeous 4 bedroom 3.5 bath waterfront home located on Pine Avenue is the perfect p ...
From $585 per night (USD)Expedia
- From $403 per night (USD)
VRBO
Zen Beach Cottage: Beautiful ground level home steps to beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Skilled craftsmanship, a tranquil atmosphere, and an unbeatable location come together at the Zen Beach Cottage, a three ...
From $403 per night (USD)VRBO
- From $488 per night (USD)
VRBO
Steps to Beach Access, Bean Point\n3-4 Bdr Mother-in-law Site Option Downstairs\n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Coco-Nut's of Anna Maria Island is the upstairs of a beautiful 3 bedroom, 2 bath home steps from the pristine white sand ...
From $488 per night (USD)VRBO
- From $520 per night (USD)
VRBO
The Cottage on Pine - Luxury Boho Beach Cottage w\/Pvt Heated Pool On Pine Ave!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Cottage on Pine! On Anna Maria Island (Anna Maria, FL) Ground Level Fully Renovated Beach Cottage in Hea ...
From $520 per night (USD)VRBO
- From $558 per night (USD)
Expedia
Summer Breeze - 5BR Anna Maria City Pool Home - By Island Real Estate Vacations
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Ready to fall in love with your new vacation home, then look no further than “Summer Breeze”. This elevated beach home i ...
From $558 per night (USD)Expedia
- From $278 per night (USD)
VRBO
Cozy couples hideaway! 5-min walk to beautiful white sand beach at Bean Point.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
❗ Flexible Check-in and checkout days —with some exceptions for holidays and certain times of the year—and never on Sun ...
From $278 per night (USD)VRBO
- From $317 per night (USD)
Expedia
Cute & cozy getaway at north end of Anna Maria Island. 5-min walk to the beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
❗ Flexible Check-in and checkout days --with some exceptions for holidays and certain times of the year—and never on Su ...
From $317 per night (USD)Expedia
- From $881 per night (USD)
VRBO
2nd House from the Beach with No Roads to Cross
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Seaside Sanctuary is the upper level unit of a beachfront duplex. It is the 2nd house from the beach with no roads ...
From $881 per night (USD)VRBO
- From $467 per night (USD)
VRBO
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CAST AWAY your stress and worries at this adorable piece of old Florida near BEAN POINT. Charming vintage cottage with L ...
From $467 per night (USD)VRBO
- From $959 per night (USD)
VRBO
Conch Shell *Pool *Hot Tub *Tiki Bar *Boat Dock *Panoramic Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Modern southern style and comfort await you at Conch Shell: A resort-like property on Bimini Bay. Meandering walkways ta ...
From $959 per night (USD)VRBO
- From $324 per night (USD)
Expedia
Bay Breeze Cottages #3
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the ...
From $324 per night (USD)Expedia
- From $1200 per night (USD)
VRBO
Bimini Bay Breeze: Canal Front | Close to Beach and Pine St. | Pool\/Spa |
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bimini Bay Breeze is a gorgeous canal front home with an expansive outdoor living area and is conveniently located close ...
From $1200 per night (USD)VRBO
- From $249 per night (USD)
Expedia
Serenity Cove: North End Cottage on Canal, Kayaks, Perfect for 2 by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
606 N. Shore Drive, #5, Anna Maria, FL 34216 What You'll Love About This Home: Location! North End AMI Canal Home! Ste ...
From $249 per night (USD)Expedia
- From $482 per night (USD)
VRBO
Chillifish: Peaceful Floridian pool home in great location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You can’t imagine anyone not falling in love with the exquisite "Chillifish" - a peaceful gem, decorated with the utmost ...
From $482 per night (USD)VRBO
- From $945 per night (USD)
Expedia
Hogfish: Stunning Southern-style large family home, minutes from Tampa Bay
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Location, location, location! Hogfish is a spacious 4 bedroom, 3 ½ bath home within walking distance to Pine Avenue, Ci ...
From $945 per night (USD)Expedia
- From $325 per night (USD)
VRBO
Bay Breeze Cottages #2
- 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 $325 per night (USD)VRBO
- From $595 per night (USD)
Expedia
AMI Peppertree Paradise - Cozy Updated Home w\/Heated Pool on North End of Island, 2 Houses to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to AMI Peppertree Paradise! On Anna Maria Island (Anna Maria, FL) 1970 sq. ft HIGHLIGHTS: - Kitchen, Dining Ar ...
From $595 per night (USD)Expedia
- From $143 per night (USD)
VRBO
☀️🌊🐟❤️Love Shack on the Water (Most Desirable Location on AMI)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Located on Pine Ave just steps from shops, the General Store, restaurants, the pier, beach, pier fishing, and the trolle ...
From $143 per night (USD)VRBO
- From $453 per night (USD)
Expedia
Come enjoy the Private Dock and Heated Pool just a short walk from the White Sandy Beaches
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Manatee Lookout is a charming 3 bedroom/3 bath home with private heated pool located on the sought after north end of An ...
From $453 per night (USD)Expedia
- From $256 per night (USD)
VRBO
Sea Spray 3: *Steps to the beach *Close to shops, restaurants *Quiet street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna Maria, West of Gulf Drive and o ...
From $256 per night (USD)VRBO
- From $390 per night (USD)
Expedia
Sea Spray 4: *Heated Pool *Pet-Friendly *Steps to beach *Shops, dining close
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Sea Spray Cottages are an adorable group of Units located in the North End of Anna Maria, West of Gulf Drive and onl ...
From $390 per night (USD)Expedia
- From $3347 per night (USD)
VRBO
Sundowner Beach: 5 BR, 5 BA House in Anna Maria, Sleeps 8
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Sundowner Beach! This luxury gulf-front property offers everything you need to enjoy the perfect beach getaw ...
From $3347 per night (USD)VRBO
- From $249 per night (USD)
Expedia
Sea Spray 1: *Pet-friendly *Steps to the beach *Close to shops, restaurants
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna Maria, West of Gulf Drive and o ...
From $249 per night (USD)Expedia
- From $234 per night (USD)
VRBO
Sea Spray 2: *Pet-friendly *Steps to the beach *Close to shops, restaurants
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna Maria, West of Gulf Drive and o ...
From $234 per night (USD)VRBO
- From $524 per night (USD)
Expedia
North Shore in Anna Maria
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
*3 Night Minimum stays are allowed during low season, please refer to the rate table for the specific date ranges* ...
From $524 per night (USD)Expedia
- From $854 per night (USD)
VRBO
EXCEPTIONAL 5 BEDROOM, 4 BATH POOL HOME IN THE CITY OF ANNA MARIA!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Exceptional 5 bedroom, 4 bath home located at the north end of Anna Maria Island. Recently renovatedhome offers top of t ...
From $854 per night (USD)VRBO
- From $474 per night (USD)
Expedia
AMI Retreat: 200 Steps to Beach, Dog Friendly Pool Home by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
746 Jacaranda Rd., Anna Maria, FL 34216 What You'll Love About This Home: Location! Located on the North End of Anna ...
From $474 per night (USD)Expedia
- From $645 per night (USD)
VRBO
Bridgeview: 5 BR, 5 BA House in Anna Maria, Sleeps 12
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Relax in this beautiful, bay view home! Bridgeview is the perfect vacation home for large family or multi-family getaway ...
From $645 per night (USD)VRBO
- From $825 per night (USD)
Expedia
Lazy Lagoon: On Canal, Pool, Boat Dock, 2 blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
220 Chilson Ave., Anna Maria, FL 34216 What You'll Love About This Home: Location! North End, 2 Blocks to the Beach & ...
From $825 per night (USD)Expedia
- From $527 per night (USD)
VRBO
Dog-friendly home with heated private pool & short walk to the beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Beach Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $527 per night (USD)VRBO
- From $1839 per night (USD)
Expedia
Villa Marisol: 4 BR, 3.5 BA House in Anna Maria, Sleeps 10
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Villa Marisol, located at 797 North Shore Drive at the north end of Anna Maria Island and nestled on the shores of the G ...
From $1839 per night (USD)Expedia
- From $464 per night (USD)
VRBO
Glad Tidings: Heated pool, turfed outdoor lounge and dining area.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Come enjoy all of the relaxation that Glad Tidings has to offer for your next island getaway! This beautiful home has re ...
From $464 per night (USD)VRBO
- From $749 per night (USD)
Expedia
Beachvergnugen - 4BR\/3BA - Anna Maria City - By Island Real Estate Vacations
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The Bean Point beach access is a favorite among locals who love surfing and soaking up sun putting “Beachvergnügen” in o ...
From $749 per night (USD)Expedia
- Click For Pricing
Expedia
Updated Canal Front Home with Private Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bimini Bay Boathouse by AMI Locals Canal front home in Anna Maria, Florida VR22-000030 Welcome to Bimini Bay Boathouse ...
Click For PricingExpedia
- From $1141 per night (USD)
Expedia
Black Pearl: 4 BR, 3 BA House in Anna Maria, Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
With 4 bedrooms and 3 full bathrooms, Black Pearl, with it's art deco décor has as much space as it does charm. In addit ...
From $1141 per night (USD)Expedia
- From $338 per night (USD)
VRBO
Canary Cottage Perfect modern cottage, quiet street, short walk to the beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Canary Cottage has 2 bedrooms and 2 full baths and will Sleep up to 6. Located in the heart of Anna Maria City- Thi ...
From $338 per night (USD)VRBO
- From $954 per night (USD)
Expedia
FantaSea - Gulf beachfront\/heated pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Private oasis back yard with a large pool and your own Beach Volleyball Court. Step out the back gate to the Gulf Beache ...
From $954 per night (USD)Expedia
- From $1565 per night (USD)
VRBO
Dream Vacation Destination! 8 bd Luxury Home with stunning Views! Pool and Spa!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 18
Highlights • 5-minute walk from the Beach • Private Pool and Hot Tub • Guest House • Ping Pong Table • Dog friendly with ...
From $1565 per night (USD)VRBO
- From $1125 per night (USD)
Expedia
Luxury Pine Ave Home! Pool, Spa, and Putting Green!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 8
Kay's Landing by AMI Locals Home in Anna Maria. FL Located on Pine Ave, in the heart of Anna Maria Highlights: - Newl ...
From $1125 per night (USD)Expedia
- From $366 per night (USD)
VRBO
Dog friendly home with a great location and close to beach! Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Sweet Melissa's Beach House by AMI Locals Home in Anna Maria, Florida VR19-000057 Welcome to Sweet Melissa’s Beach H ...
From $366 per night (USD)VRBO
- From $763 per night (USD)
Expedia
Pete's Blue Heaven: 4 BR, 2 BA House in Anna Maria, Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Plan your next island vacation at this exception 4 bedroom, 2 bath home located at the north end of Anna Maria! Enjoy th ...
From $763 per night (USD)Expedia
- From $470 per night (USD)
VRBO
Luxury bungalow with pool and spa! Canal front with dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Bamboo Bungalow by AMI Locals Home in Anna Maria VR19-000043 Welcome to the Bamboo Bungalow, a canal-front home where ...
From $470 per night (USD)VRBO
- Click For Pricing
VRBO
Stonehenge: Charming, vintage ground-level cottage with heated pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located at the north end of Anna Maria, Stonehenge is a charming, vintage ground level cottage. You will find this char ...
Click For PricingVRBO
- From $529 per night (USD)
VRBO
Bon Ami: North End AMI, Pool Home, Short Walk to Bean Point by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
804 North Bay Blvd., Anna Maria, FL 34216 What You'll Love About This Home: Location! Located just 1 block from Bean ...
From $529 per night (USD)VRBO
- From $239 per night (USD)
Expedia
Naut 2 Shabby Bungalow 🤗 | A sweet and cozy getaway on Pine Avenue!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
❗ Check-in and checkout days are typically Monday or Friday—with some exceptions for holidays and certain times of the ...
From $239 per night (USD)Expedia
- From $750 per night (USD)
VRBO
Charming Beach Home-w\/large Pool - Only 3 Houses from the Beach, Near Pine Ave!!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relaxing 'Home Away from Home' Tropical Paradise - 3 Houses from the beach. Located on the quiet, North end of the Islan ...
From $750 per night (USD)VRBO
- From $235 per night (USD)
Expedia
Anna Cabana A: North End Pool Home, Short Walk To Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
770 Jacaranda Rd., Anna Maria, FL 34216 What you'll love about this home: Location! On the North End of Anna Maria 2 b ...
From $235 per night (USD)Expedia
- From $415 per night (USD)
VRBO
Charming Beach house sits amongst huge Banyan Trees, walk to beach & Pine Ave.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
****UP TO 8 PEOPLE WITH ADDITONAL PRIVATE SUITE, ASK OWNER FOR AVAILABILITY**** Voted a Tropical paradise, feels like y ...
From $415 per night (USD)VRBO
- From $682 per night (USD)
Expedia
The Beach House 2 by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Beach House 2! Enjoy absolute beachfront on the north end of Anna Maria. Directly on the Gulf of Mexico, ...
From $682 per night (USD)Expedia
- From $516 per night (USD)
VRBO
Decked Out - Stunning Home! Huge Sunny Resort Style Heated Pool, Walk to Pine Ave & Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Decked Out! On Anna Maria Island (Anna Maria, FL) A gorgeous home filled with luxurious furnishings, high-en ...
From $516 per night (USD)VRBO
- From $641 per night (USD)
Expedia
Aloha Fern: North End Beach House, Walk to Bean Point & Rod & Reel by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
702 Fern, Anna Maria, FL 34216 What You'll Love About This Home: Location! Walking Distance to Bean Point & Rod & Reel! ...
From $641 per night (USD)Expedia