Anna Maria Rentals
- From $2529 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 $2529 per night (USD)VRBO
- From $1396 per night (USD)
Expedia
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)Expedia
- From $1749 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 $1749 per night (USD)VRBO
- From $644 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 $644 per night (USD)Expedia
- From $487 per night (USD)
VRBO
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 $487 per night (USD)VRBO
- From $1116 per night (USD)
Expedia
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 $1116 per night (USD)Expedia
- 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 $520 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 $520 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 $199 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 $199 per night (USD)Expedia
- From $299 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 $299 per night (USD)VRBO
- From $648 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 $648 per night (USD)Expedia
- 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 $771 per night (USD)
Expedia
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 $771 per night (USD)Expedia
- From $393 per night (USD)
VRBO
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)VRBO
- From $588 per night (USD)
Expedia
A Ray Of Sunshine- Amazing property private basketball court pool\/spa on a canal
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A Ray of Sunshine 232 Chilson Avenue Anna Maria Island, FL 34216 AT A GLANCE Newly remodeled professionally decorated ...
From $588 per night (USD)Expedia
- From $985 per night (USD)
VRBO
Anapauo Beachhouse: Million dollar views of Tampa Bay!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Anapauo Beachhouse! Pronounced ahn-ap-ow’-o, it is a Greek word meaning to give rest, refresh, recover and co ...
From $985 per night (USD)VRBO
- From $392 per night (USD)
Expedia
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 $392 per night (USD)Expedia
- From $452 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 $452 per night (USD)VRBO
- From $576 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 $576 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 $944 per night (USD)
VRBO
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 $944 per night (USD)VRBO
- From $1221 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 Less than a 5-minute walk from the pristine Gulf beaches Highlights: - ...
From $1221 per night (USD)Expedia
- From $298 per night (USD)
VRBO
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)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 $389 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 $389 per night (USD)VRBO
- From $1292 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 $1292 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 $438 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 $438 per night (USD)Expedia
- From $395 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 $395 per night (USD)VRBO
- From $525 per night (USD)
Expedia
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 $525 per night (USD)Expedia
- From $290 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 $290 per night (USD)VRBO
- From $300 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 $300 per night (USD)Expedia
- From $891 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 $891 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 $368 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 $368 per night (USD)VRBO
- From $926 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 $926 per night (USD)Expedia
- From $299 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 $299 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 $460 per night (USD)
VRBO
Manatee Lookout by SeaBreeze Vacation
- 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 $460 per night (USD)VRBO
- From $297 per night (USD)
Expedia
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 $297 per night (USD)Expedia
- From $414 per night (USD)
VRBO
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 $414 per night (USD)VRBO
- From $3453 per night (USD)
Expedia
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 $3453 per night (USD)Expedia
- From $302 per night (USD)
VRBO
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 $302 per night (USD)VRBO
- From $735 per night (USD)
Expedia
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 $735 per night (USD)Expedia
- From $269 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
746 Jacaranda Rd., Anna Maria, FL 34216 What You'll Love About This Home: Location! Located on the North End of Anna ...
From $269 per night (USD)VRBO
- From $770 per night (USD)
Expedia
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 $770 per night (USD)Expedia
- From $843 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
220 Chilson Ave., Anna Maria, FL 34216 What You'll Love About This Home: Location! North End, 2 Blocks to the Beach & ...
From $843 per night (USD)VRBO
- From $469 per night (USD)
Expedia
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 $469 per night (USD)Expedia
- From $1772 per night (USD)
VRBO
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 $1772 per night (USD)VRBO
- From $321 per night (USD)
Expedia
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 $321 per night (USD)Expedia
- From $674 per night (USD)
VRBO
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 $674 per night (USD)VRBO
- From $478 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 $478 per night (USD)Expedia
- From $1590 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 $1590 per night (USD)VRBO
- From $1386 per night (USD)
Expedia
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 $1386 per night (USD)Expedia
- From $358 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 $358 per night (USD)VRBO
- From $357 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 $357 per night (USD)Expedia
- From $235 per night (USD)
VRBO
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 $235 per night (USD)VRBO
- From $700 per night (USD)
Expedia
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 $700 per night (USD)Expedia
- From $475 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 $475 per night (USD)VRBO
- From $248 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 $248 per night (USD)Expedia
- From $519 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 $519 per night (USD)VRBO
- From $1619 per night (USD)
Expedia
Beaches and Dreams: 4 BR, 4.5 BA House in Anna Maria, Sleeps 8
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Ultimate Beach Front Paradise on Anna Maria Island at Beaches & Dreams where the stunning panoramic views ...
From $1619 per night (USD)Expedia
- Click For Pricing
Expedia
North Pointe | Bright and cozy north end home, heated pool, steps to Bean Point!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
❗ Check-in and checkout days are typically Monday or Friday—with some exceptions for holidays and certain times of the ...
Click For PricingExpedia
- From $460 per night (USD)
Expedia
Canal-front home with private dock, covered lanai with heated pool and grill
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Coconut Tree Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $460 per night (USD)Expedia
- From $468 per night (USD)
VRBO
Dog-friendly house w\/ heated private lagoon pool - two blocks from the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
LaRaya Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $468 per night (USD)VRBO
- From $401 per night (USD)
Expedia
Dog-friendly house with heated private pool, island views & nearby beach access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Shell House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $401 per night (USD)Expedia
- From $324 per night (USD)
VRBO
Beautiful cottage w\/ heated private pool - walk to beach, dining, Bayfront Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Harmony House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $324 per night (USD)VRBO
- From $477 per night (USD)
Expedia
Beautiful, well-maintained home w\/ heated private pool - walk to beach & dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sundance Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $477 per night (USD)Expedia
- From $409 per night (USD)
VRBO
Old Florida-style cottage w\/ private heated pool - walk to the beach - dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Mangrove Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $409 per night (USD)VRBO
- From $436 per night (USD)
Expedia
High-end home w\/ heated private pool\/spa, courtyard, & floor-to-ceiling windows
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Dream Maker Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $436 per night (USD)Expedia
- From $669 per night (USD)
VRBO
Canalfront Island Gem with Private Heated Pool, Dock, Ping-Pong, & Putting Green
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Mermaid Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $669 per night (USD)VRBO
- From $112 per night (USD)
Expedia
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Anna Maria's Finest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $112 per night (USD)Expedia
- From $366 per night (USD)
VRBO
Charming gulf-front home right on the beach - stunning views, dogs welcome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Dolphin Watch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $366 per night (USD)VRBO
- From $255 per night (USD)
Expedia
Waterfront dog-friendly bungalow w\/ bay views - watch for dolphins from deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Grant's View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $255 per night (USD)Expedia
- From $688 per night (USD)
VRBO
Incredible, spacious home with a private heated pool - close to the beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Le Paradis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $688 per night (USD)VRBO
- From $364 per night (USD)
Expedia
Canalfront home w\/ WiFi, heated pool, dock & lanai - 2 blocks to the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Heavenly Holly Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $364 per night (USD)Expedia
- From $759 per night (USD)
VRBO
Breezy canalfront home w\/ heated pool & dock - 3 blocks to Bean Point Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Paradise Pointe Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $759 per night (USD)VRBO
- From $393 per night (USD)
Expedia
Adorable Cottage with Heated Pool - Fantastic Location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Buttonwood Cottage by AMI Locals Home in Anna Maria, Florida Full of old Florida charm and recently restored, we welcom ...
From $393 per night (USD)Expedia
- From $1293 per night (USD)
VRBO
Gulf Front Home with Amazing Views!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Happy Ours by AMI Locals Home in Anna Maria, FL Highlights: • Gulf Front • Back porch with grill • Updated kitchen feat ...
From $1293 per night (USD)VRBO
- From $958 per night (USD)
Expedia
Enjoy \"Endless Summer\" at this awesome luxury beach house with your family!
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 14
Endless Summer by Anna Maria Island Locals Home in Anna Maria, FL Just one street over from Pine Ave Highlights: - Bea ...
From $958 per night (USD)Expedia
- From $1272 per night (USD)
VRBO
Serendipity Gulfront- gulf beach front
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Gulf Beach Front 3 bedroom/3 bathroom home and separate 1/1 cottage Sunset's from your back deck and morning shell sear ...
From $1272 per night (USD)VRBO
- From $636 per night (USD)
Expedia
Water views- 4 bedroom\/2 bath
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Sky by Serendipity is a unique, elevated island home with 4 bedrooms and 2 bathrooms. Conveniently located on the north ...
From $636 per night (USD)Expedia
- From $1449 per night (USD)
VRBO
TripleTail- beachfront 4\/4
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
4 bedroom 4 bath Beach Front Home with Panoramic views of the Ocean and Skyway Bridge. Watch dolphins swim and play in y ...
From $1449 per night (USD)VRBO
- From $595 per night (USD)
Expedia
Point's Hideaway - Beautiful Home w\/Stunning Sunset\/Water Views on Bean Point! Pool, Bar, Foosball!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Point's Hideaway! On Anna Maria Island (Anna Maria, FL) HIGHLIGHTS: - Kitchen, Dining, Living w/ TV - 1 King ...
From $595 per night (USD)Expedia
- From $847 per night (USD)
VRBO
Luxury home, close to the beach! Pool and Spa, great for families!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Freckled Fin by AMI Locals Home in Anna Maria, Florida VR19-000006 Welcome to Freckled Fin, a fun and luxurious vacati ...
From $847 per night (USD)VRBO
- From $720 per night (USD)
Expedia
Canal front home with a pool and boat dock!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • Canalfront with dock • 5-minute walk to the beach • Private pool • Putting green • Pool Table and Ping Po ...
From $720 per night (USD)Expedia
- From $951 per night (USD)
VRBO
Historic 1924 Luxury Beach Home with Large Heated Pool 3 Houses to Beach
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Sand Castle located just a few steps from the Gulf beaches of Anna Maria Island. Built in 1924, the Castl ...
From $951 per night (USD)VRBO
- Click For Pricing
Expedia
Starfish Cottage the largest of a cluster of 3 properties sharing a free form pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Idyllic Holiday Properties is a small friendly holiday company offering an honest and efficient service for our privatel ...
Click For PricingExpedia
- From $385 per night (USD)
VRBO
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
OHasis Getaway is a true oasis on both the outside and inside! When you step into our vacation rental, your eyes are im ...
From $385 per night (USD)VRBO
- From $404 per night (USD)
Expedia
C-View by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
C-View is the perfect island getaway for your family vacation. Conveniently located within walking distance to Anna Mari ...
From $404 per night (USD)Expedia
- From $406 per night (USD)
VRBO
Colorful beach cottage w\/ heated private pool & grill area - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sea's The Day Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $406 per night (USD)VRBO
- From $440 per night (USD)
Expedia
Waterfront home near beaches with private heated pool, spa, and more
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Surrounded By Sea Breezes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $440 per night (USD)Expedia
- From $332 per night (USD)
VRBO
Sunny dog-friendly cottage with spacious patio and grill, steps from the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Seashell Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $332 per night (USD)VRBO
- From $493 per night (USD)
Expedia
La Cocolia in Anna Maria
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Need a GREAT AMI GETAWAY? Just steps from the bayfront park in the City of Anna Maria is a charming island beach house ...
From $493 per night (USD)Expedia
- Click For Pricing
VRBO
Whispering Pines: AMI North End, Steps to Beach, Dog Friendly by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
213 Spruce Ave., Anna Maria, FL 34216 What you'll love about this home: Location! On the North End of Anna Maria & 3 h ...
Click For PricingVRBO
- From $543 per night (USD)
Expedia
North End of Anna Maria Island with Spectacular Views from the Primary EnSuite
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Moon Shadow South's location can't be beat with views of Passage Key in Tampa Bay from the Primary Ensuite. You are just ...
From $543 per night (USD)Expedia
- From $275 per night (USD)
VRBO
Seas The Day: North End Canal Front, Fishing Dock & Kayaks by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
522 Bayview Place, Anna Maria, FL 34216 What You'll Love About This Home: Location - North End on a Canal with Private ...
From $275 per night (USD)VRBO
- From $918 per night (USD)
Expedia
My Private Beach: Waterfront Pool Home on the Bay by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
826A South Bay Blvd., Anna Maria, FL 34216 What You'll Love About This Home: Location! Your own private sandy beach on ...
From $918 per night (USD)Expedia