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 $779 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 $779 per night (USD)
VRBO
From $555 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 $555 per night (USD)
Expedia
From $856 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 $856 per night (USD)
VRBO
$Beachy Keen 408 - Anna Maria Island - Private home 3 Bedroom\/ 2 Bath with...$
From $563 per night (USD)
Expedia
Beachy Keen 408 - Anna Maria Island - Private home 3 Bedroom\/ 2 Bath with...
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 $563 per night (USD)
Expedia
$A Ray Of Sunshine- Amazing property private basketball court pool\/spa on a canal$
From $674 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 $674 per night (USD)
VRBO
From $1016 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 $1016 per night (USD)
Expedia
From $636 per night (USD)
VRBO
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 $636 per night (USD)
VRBO
From $1825 per night (USD)
Expedia
Felicity: Luxury Bayfront Home, Heated Pool, Hot tub and more!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Beachfront Felicity in Anna Maria Welcome to Felicity (formerly known as Bay Breeze)! This is one of the most exclusive ...
From $1825 per night (USD)
Expedia
From $642 per night (USD)
VRBO
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 $642 per night (USD)
VRBO
$707 N Bay The Shell House - Anna Maria Island - Private home 3 Bedroom\/ 2 1\/2...$
From $517 per night (USD)
Expedia
707 N Bay The Shell House - Anna Maria Island - Private home 3 Bedroom\/ 2 1\/2...
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 $517 per night (USD)
Expedia
From $674 per night (USD)
VRBO
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 $674 per night (USD)
VRBO
From $1018 per night (USD)
Expedia
2nd floor Condo with Beach and Pool Access - Coconuts Gulf View #118
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Coconuts Gulf Views #118 by AMI Locals Condo in Holmes Beach, Florida VRC21-000172 Let the good times roll at Coconu ...
From $1018 per night (USD)
Expedia
From $1754 per night (USD)
VRBO
Stunning new luxury home, pool + spa, walk to the beach! Summer awaits!
Bedrooms:
7
Bathrooms:
7
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 $1754 per night (USD)
VRBO
From $362 per night (USD)
Expedia
A Shore Thing - Relaxing Island Living , Large Heated Pool, Boat Lift
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
This beach house is "A Shore Thing" for creating fantastic vacation memories. This newly furnished ground level home is ...
From $362 per night (USD)
Expedia
From $688 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 $688 per night (USD)
VRBO
From $1492 per night (USD)
Expedia
Gorgeous Canal Front Luxury home, Pool, Spa, Dock, and Rooftop Deck - Sail Away
Bedrooms:
7
Bathrooms:
6
Sleeps:
8
Sail Away by AMI Locals Home in Anna Maria, FL VR19-000048 Welcome to Sail Away—an exquisite six-bedroom, six-and-a-h ...
From $1492 per night (USD)
Expedia
$Lakeside Beach House 3\/2 Pool Home Outdoor Kitchen Close to Beach$
From $472 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 $472 per night (USD)
VRBO
$Stunning 3Bed\/3 Bath, Heated Pool, FREE WiFi, Close to Beach, On Canal to...$
From $613 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 $613 per night (USD)
Expedia
$Relaxing Home with Private Pool, High-Speed WiFi, Central AC, & Washer\/Dryer$
From $722 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 $722 per night (USD)
VRBO
From $524 per night (USD)
Expedia
Vibrant retreat with pool, beach access, tennis, balcony, & stunning ocean views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gulf Place 19 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $524 per night (USD)
Expedia
From $732 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 $732 per night (USD)
VRBO
From $1468 per night (USD)
Expedia
⚓Bay Dreamin! Walk to the Beach, Pier, & Pine Ave! Heated Pool!⚓⛳🏖🌅
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Have you been dreaming about the water here on Floridas Beautiful Gulf Coast? Well, come enjoy "Bay Dreamin" *Construc ...
From $1468 per night (USD)
Expedia
$BEACH FRONT, 2 Bd\/2 Bath, FREE WiFi & Trolley, Heated Pool and Awesome Sunsets$
From $476 per night (USD)
VRBO
BEACH FRONT, 2 Bd\/2 Bath, FREE WiFi & Trolley, Heated Pool and Awesome Sunsets
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
**ASK ABOUT LAST MINUTE DEALS! Enjoy a fabulous stay at the beach in this beautifully remodeled two bedroom ...
From $476 per night (USD)
VRBO
From $1254 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 $1254 per night (USD)
Expedia
From $843 per night (USD)
VRBO
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 $843 per night (USD)
VRBO
From $703 per night (USD)
Expedia
Beachfront - Sandy Turtle by SeaBreeze Vacation
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located on the tranquil beaches of Anna Maria Island, Sandy Turtle is mere steps away from the beach and offers pictures ...
From $703 per night (USD)
Expedia
From $886 per night (USD)
VRBO
Sweet Retreat Cottage: Ground level cottage across the street from the beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This Anna Maria Island rental was given the name Sweet Retreat Cottage for a reason. Offering a private heated pool, vie ...
From $886 per night (USD)
VRBO
From $606 per night (USD)
Expedia
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 $606 per night (USD)
Expedia
$Steps to Beach Access, Bean Point\n3-4 Bdr Mother-in-law Site Option Downstairs\n$
From $565 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 $565 per night (USD)
VRBO
From $747 per night (USD)
Expedia
Gulf Front 1 Bedroom Condo - Amazing Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Coconuts Beachfront #112 Condo in Holmes Beach, Florida VRC21-000175 Your dream beach vacation awaits at Coconuts Beach ...
From $747 per night (USD)
Expedia
$The Cottage on Pine - Charming Pine Ave Cottage w\/ Heated Pool in the Heart of Anna Maria Island$
From $675 per night (USD)
VRBO
The Cottage on Pine - Charming Pine Ave Cottage w\/ Heated Pool in the Heart of Anna Maria Island
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to The Cottage on Pine! On Anna Maria Island (Anna Maria, FL) After sustaining hurricane damage, this charming ...
From $675 per night (USD)
VRBO
$Mango Bay – Luxury 4BR w\/ Heated Pool, Spa & Game Room$
From $800 per night (USD)
Expedia
Mango Bay – Luxury 4BR w\/ Heated Pool, Spa & Game Room
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Mango Bay! On Anna Maria Island (Holmes Beach, FL) 3,000 sqft of a Beautifully Restored Island Home with Poo ...
From $800 per night (USD)
Expedia
From $878 per night (USD)
VRBO
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 $878 per night (USD)
VRBO
From $374 per night (USD)
Expedia
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 Sunday ...
From $374 per night (USD)
Expedia
From $389 per night (USD)
VRBO
Cute & cozy getaway at north end of Anna Maria Island. 5-min walk to the beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located at the quiet North end of Anna Maria Island, this charming 2-bedroom, 1-bath villa is a short walk to beautiful ...
From $389 per night (USD)
VRBO
From $1078 per night (USD)
Expedia
Golf Cart, Salty Shamrock by SeaBreeze Vacation
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be ov ...
From $1078 per night (USD)
Expedia
From $404 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 $404 per night (USD)
VRBO
From $372 per night (USD)
Expedia
AM I Dreaming: Heated Pool, Family Friendly Home, 3-min walk to beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The vacation you have imagined finally becomes a reality. AM I dreaming is a bright and charming 3 bedroom, 2 bathroom c ...
From $372 per night (USD)
Expedia
From $518 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 $518 per night (USD)
VRBO
$217 84th - Anna Maria Island- Private home 3 Bedroom\/ 2 Bath with private...$
From $254 per night (USD)
Expedia
217 84th - Anna Maria Island- Private home 3 Bedroom\/ 2 Bath with private...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
217 84th Street - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC#20-000113 Private Poo ...
From $254 per night (USD)
Expedia
$Sand Of Times-Beautiful 6 bedrooms with private pool\/spa with a water slide$
From $1127 per night (USD)
VRBO
Sand Of Times-Beautiful 6 bedrooms with private pool\/spa with a water slide
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Sands of Time 6908 Holmes Blvd Holmes Beach, FL 34217 Sands of Time is a newly built 6 bedroom, 4.5 bathroom vacation ...
From $1127 per night (USD)
VRBO
From $1094 per night (USD)
Expedia
Pool*Hot Tub*Tiki Bar*Pickleball Court*Dock
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 $1094 per night (USD)
Expedia
From $447 per night (USD)
VRBO
Bay Breeze Cottages #3
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the ...
From $447 per night (USD)
VRBO
From $829 per night (USD)
Expedia
Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
If you are looking to enjoy Anna Maria Island in a beautiful home, look no further than "Sunny Side of the Beach" on 66t ...
From $829 per night (USD)
Expedia
From $525 per night (USD)
VRBO
Cuddlefish Cove: Heated Pool, rooftop deck, gorgeous views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Cuddlefish Cove Your flip flops have found a new retreat by the beach! Stay for a week or a month at this dazzling Key W ...
From $525 per night (USD)
VRBO
$Island Walk 313 - Anna Maria Island - Townhouse 3 Bedroom\/ 2 .5 Bath with...$
From $403 per night (USD)
Expedia
Island Walk 313 - Anna Maria Island - Townhouse 3 Bedroom\/ 2 .5 Bath with...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Island Walk 313 - Anna Maria Island - Townhouse - 3 Bedroom/ 2 .5 Bath, maximum occupancy of 6 people. VRC16-000052 ...
From $403 per night (USD)
Expedia
$Bimini Bay Breeze: Canal Front | Close to Beach and Pine St. | Pool\/Spa |$
From $1313 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 $1313 per night (USD)
VRBO
From $385 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
Serenity Cove by Anna Maria Life Vacation Rentals 606 N. Shore Drive, #5, Anna Maria, FL 34216 What You'll Love About T ...
From $385 per night (USD)
Expedia
From $1090 per night (USD)
VRBO
Silver Surf- A stunning family home 2 blocks from the beach.
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
The minute you walk in the front door at Silver Surf you'll be convinced that you're about to experience the very best o ...
From $1090 per night (USD)
VRBO
From $1577 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 $1577 per night (USD)
Expedia
Click For Pricing
VRBO
Beach Bay Serenity: Pine Ave canal front pool home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If you enjoy salt air and sea breezes, morning coffee on your patio, walking miles and miles of white sandy beach and sw ...
Click For Pricing
VRBO
From $392 per night (USD)
Expedia
Bay Breeze Cottages #2
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 $392 per night (USD)
Expedia
$AMI Peppertree Paradise - Steps to Beach, Private Pool, Coastal Retreat w\/ Outdoor Oasis$
From $641 per night (USD)
VRBO
AMI Peppertree Paradise - Steps to Beach, Private Pool, Coastal Retreat w\/ Outdoor Oasis
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to AMI Peppertree Paradise! On Anna Maria Island (Anna Maria, FL) Enjoy a sun-soaked getaway at AMI Peppertree ...
From $641 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Seaside Beach House 203 | Gulf-Front Escape with Panoramic Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
VRC20-000296 Wake up to breathtaking Gulf views and fall asleep to the sound of the waves at Seaside Beach House 203, a ...
From $388 per night (USD)
Expedia
From $190 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 $190 per night (USD)
VRBO
From $533 per night (USD)
Expedia
Private Dock - Manatee Lookout by SeaBreeze Vacation
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Manatee Lookout is a charming 3 bedroom/3 bath home with a private heated pool located on the sought after north end of ...
From $533 per night (USD)
Expedia
From $602 per night (USD)
VRBO
Florida Breeze: Pool home in perfect central location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Florida Breeze is the perfect vacation rental for your next trip to Anna Maria Island! The location with the short walk ...
From $602 per night (USD)
VRBO
From $318 per night (USD)
Expedia
Sea Spray 3: *Steps to the beach *Close to shops, restaurants *Quiet street
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
***Photos Updated April 2025*** The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna ...
From $318 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Sea Spray 4: *Heated Pool *Pet-Friendly *Steps to beach *Shops, dining close
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*** Photos Updated April 2025*** The Sea Spray Cottages are an adorable group of Units located in the North End of Anna ...
From $469 per night (USD)
VRBO
$Turtle Nest! New Holiday House w\/ Pool, Wifi, and Access to the Beach$
From $586 per night (USD)
Expedia
Turtle Nest! New Holiday House w\/ Pool, Wifi, and Access to the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Remodeled in 2025, this comfortable and tastefully furnished home offers everything you need for a relaxed vacation with ...
From $586 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Home with Private Outdoor Living Space, Community Pool - Sea La Vie
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea La Vie by AMI Locals Condo in Holmes Beach, Florida VRC21-000203 Welcome to Sea La Vie! This three-bedroom, three- ...
From $295 per night (USD)
VRBO
From $2637 per night (USD)
Expedia
Sundowner Beach: Luxury Gulf-front, stunning views
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 $2637 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Sea Spray 1: *Pet-friendly *Steps to the beach *Close to shops, restaurants
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
***Photos Updated April 2025*** The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna ...
From $284 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Sea Spray 2: *Pet-friendly *Steps to the beach *Close to shops, restaurants
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
***Photos Updated April 2025*** The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna ...
From $277 per night (USD)
Expedia
From $779 per night (USD)
VRBO
North Shore Very Walkable to AMI fun & close to the Beach, Stunning Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Discover island paradise at North Shore located on the *premier corner* of North Shore & Palmetto in Anna Maria, only 2 ...
From $779 per night (USD)
VRBO
From $574 per night (USD)
Expedia
Charming Private Home, Private Pool and Spa. Fenced Yard, Updates Throughout
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Seahorse Cottage by AMI Locals Home in Holmes, Beach Florida VRC16-000110 Enjoy a luxury vacation with friends and fami ...
From $574 per night (USD)
Expedia
From $622 per night (USD)
VRBO
AMI Retreat: 200 Steps to Beach, Dog Friendly Pool Home by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
AMI Retreat by Anna Maria Life Vacation Rentals 746 Jacaranda, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $622 per night (USD)
VRBO
From $1072 per night (USD)
Expedia
Bridgeview: Bay front with sweeping views, 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 $1072 per night (USD)
Expedia
From $865 per night (USD)
VRBO
Lazy Lagoon: On Canal, Pool, Boat Dock, 2 blocks to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Lazy Lagoon by Anna Maria Life Vacation Rentals 220 Chilson Ave., Anna Maria, FL 34216 What You'll Love About This Home ...
From $865 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Island Time: Gulf front condo 20 ft to the beach with shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Time 104 at Seaside Beach House is a condominium that has long been a favorite to visitors of Holmes Beach and An ...
From $386 per night (USD)
Expedia
Click For Pricing
VRBO
Resort Sixty-Six, Holmes Beach, Florida, 1 Bedroom Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
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 Pricing
VRBO
Click For Pricing
Expedia
Amazing Resort Sixty-Six, 1 Bedroom Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
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 Pricing
Expedia
$Villa Marisol: Beachfront, Mediterranean style, w\/terrace, pool, hot tub!$
From $1780 per night (USD)
VRBO
Villa Marisol: Beachfront, Mediterranean style, w\/terrace, pool, hot tub!
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 $1780 per night (USD)
VRBO
From $587 per night (USD)
Expedia
Glad Tidings: Heated pool, turfed outdoor lounge and dining area.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Photos updated March 2025! Welcome to Glad Tidings, a comfortable and well-appointed vacation home on Anna Maria Island ...
From $587 per night (USD)
Expedia
$Sunset at 714 - 4BR\/3BA - Anna Maria City - By Island Real Estate Vacations$
From $849 per night (USD)
VRBO
Sunset at 714 - 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 “Sunset at 714” in on ...
From $849 per night (USD)
VRBO
From $383 per night (USD)
Expedia
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 $383 per night (USD)
Expedia
$FantaSea - Gulf beachfront\/heated pool$
From $1888 per night (USD)
VRBO
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 $1888 per night (USD)
VRBO
From $429 per night (USD)
Expedia
Egret at Blue Lagoon on Anna Maria Island - By Island Real Estate Vacations
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just perfect! From the tasteful beachy decor to the fully appointed kitchen you won’t find more welcoming accommodations ...
From $429 per night (USD)
Expedia
From $1879 per night (USD)
VRBO
Dream Vacation Destination! 8 bd Luxury Home with stunning Views! Pool and Spa!
Bedrooms:
6
Bathrooms:
8
Sleeps:
18
Blue Bay by Anna Maria Island Accommodations Home in Anna Maria, Florida VR16-000138 Welcome to Blue Bay – Your Lux ...
From $1879 per night (USD)
VRBO
From $790 per night (USD)
Expedia
Perfect 1-bedroom Beachfront Getaway!! See the sunsets and feel the breeze!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Highlights: -large bay of windows perfectly frame the beach from the kitchen, living, and dining areas -Screened porch - ...
From $790 per night (USD)
Expedia
From $638 per night (USD)
VRBO
Home with Pool! Near Beach, Bay, and Pier! - Sweet Melissa's Beach House
Bedrooms:
3
Bathrooms:
4
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 $638 per night (USD)
VRBO
$Pete's Blue Heaven: Steps to beach w\/heated pool$
From $1041 per night (USD)
Expedia
Pete's Blue Heaven: Steps to beach w\/heated pool
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 $1041 per night (USD)
Expedia
From $722 per night (USD)
VRBO
Summer Wind- An island getaway in the perfect location.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience all the best elements of the perfect Island vacation in this well-appointed rental home. It is located just a ...
From $722 per night (USD)
VRBO
From $754 per night (USD)
Expedia
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 $754 per night (USD)
Expedia
From $972 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
Bon Ami by Anna Maria Life Vacation Rentals 804 North Bay Blvd., Anna Maria, FL 34216 What You'll Love About This Home: ...
From $972 per night (USD)
VRBO
From $343 per night (USD)
Expedia
Island Hideaway East: 5 Minute Walk to Beach, Private Pool by Anna Maria Life Vacation Rentals
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Island Hideaway East by Anna Maria Life Vacation Rentals 308B 67th St., Holmes Beach, FL 34217 What you'll love about t ...
From $343 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Anna Cabana A: North End Pool Home, Short Walk To Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Anna Cabana A by Anna Maria Life Vacation Rentals 770 Jacaranda Rd., Anna Maria, FL 34216 What you'll love about this h ...
From $368 per night (USD)
VRBO
From $478 per night (USD)
Expedia
Dream luxury home on Anna Maria Island, heated private pool - pet friendly!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
This lovely new island 2 bedrooms, 2.5 baths luxury home with private heated pool is a dream. Fishful Thinking is positi ...
From $478 per night (USD)
Expedia
From $440 per night (USD)
VRBO
3 bedroom, on AMI, heated private pool, PET FRIENDLY!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The family friendly Florida vacation you need is waiting at Mykonos! This Anna Maria Island beach rental has it all. Fro ...
From $440 per night (USD)
VRBO
From $1244 per night (USD)
Expedia
Conch House - 7 Homes to the Beach - Amazing Pool Area with TV
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to the Conch House, a Charleston inspired beach house unlike any other home and without compromise in craftsmans ...
From $1244 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Cozy Retro Cottage located less then 2 blocks from the Gulf Beach - Heated Pool in Private Oasis!
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Welcome to Flip Cottage located just 1 block from the Gulf beaches of Anna Maria Island. Flip is a ground level half dup ...
From $365 per night (USD)
VRBO
$Beachfront Condo w\/ Large Balcony & Beautiful Views of Gulf of Mexico$
Click For Pricing
Expedia
Beachfront Condo w\/ Large Balcony & Beautiful Views of Gulf of Mexico
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
NOTE: the elevator at this property are currently not available. Imagine waking up every morning to a million dollar v ...
Click For Pricing
Expedia
$Decked Out - Luxury 2BR Retreat w\/ Heated Pool & Prime Location$
From $663 per night (USD)
VRBO
Decked Out - Luxury 2BR Retreat w\/ Heated Pool & Prime Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Decked Out! On Anna Maria Island (Anna Maria, FL) Experience the ultimate island retreat at Decked Out, a lu ...
From $663 per night (USD)
VRBO
From $322 per night (USD)
Expedia
AMI Sand Dollar: Dog Friendly, Private Pool, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
AMI Sand Dollar by Anna Maria Life Vacation Rentals 6403 B Holmes Blvd, Holmes Beach, FL 34217 What You'll Love About T ...
From $322 per night (USD)
Expedia
From $1182 per night (USD)
VRBO
Barefoot Bungalow:Dog Friendly, Screened Pool, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Barefoot Bungalow by Anna Maria Life Vacation Rentals 213 70th St., Holmes Beach, FL 34217 What You'll Love About This ...
From $1182 per night (USD)
VRBO
From $348 per night (USD)
Expedia
AMI Starfish: Private Pool, Dog Friendly, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AMI Starfish by Anna Maria Life Vacation Rentals 6403 A Holmes Blvd., Holmes Beach, FL 34217 What You'll Love About Thi ...
From $348 per night (USD)
Expedia
From $1117 per night (USD)
VRBO
Aloha Fern: North End Beach House, Pool by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Aloha Fern by Anna Maria Life Vacation Rentals 702 Fern, Anna Maria, FL 34216 What You'll Love About This Home: Locatio ...
From $1117 per night (USD)
VRBO
From $1948 per night (USD)
Expedia
Beaches and Dreams: Ultimate Luxury Beachfront Paradise
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to the Ultimate Beach Front Paradise on Anna Maria Island at Beaches & Dreams, where stunning panoramic bay view ...
From $1948 per night (USD)
Expedia
From $862 per night (USD)
VRBO
Beautiful New Pool Home with Gulf Views and Heated pool, steps to Bean Point!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We are excited to announce that our popular vacation rental is back on the market after a complete renovation! Everythin ...
From $862 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Island villa with heated private pool, tranquil courtyard, easy beach access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Blue Wave Villa West Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $444 per night (USD)
Expedia

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