Anna Maria Rentals
From $1178 per night (USD)VRBO
North Shore Beach House: Tranquil 4BR Retreat with Pool, Spa, & Walk to Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to North Shore Beach House, your serene sanctuary on the North End of Anna Maria Island. This stunning 4-bedroom, ...
From $1178 per night (USD)VRBO
From $620 per night (USD)VRBO
Bean Point Beach Cottage -North End of Island beautiful white sand and sunsets!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bean Point Beach. Vacation at Anna Maria Island with the most beautiful white sands beach and crystal clear emerald gree ...
From $620 per night (USD)VRBO
From $626 per night (USD)VRBO
Anna Maria island 3 bedroom, private pool and pet friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Coconut Bayou is a 3 bedroom, 3.5 bath Key West style beauty with all the comforts you may think of. Just a few minutes ...
From $626 per night (USD)VRBO
From $871 per night (USD)Expedia
Mia Bella walk to beach on canal 2 king suites AMI private dock/pool villa
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Create unforgettable memories at Mia Bella located on Hammock Road, just north of Pine Avenue, in a *premier deep water ...
From $871 per night (USD)Expedia
From $1260 per night (USD)VRBO
Luxury Home with Pathway to the Beach! Secluded Pool and Spa!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Coastal Couture by AMI Locals Home in Anna Maria, Florida VR21-000085 Welcome to Coastal Couture! This luxurious mul ...
From $1260 per night (USD)VRBO
From $581 per night (USD)Expedia
Mermaid House Rooftop deck, Gulf views, beautiful home, steps to the sand!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
If you love this rental but are not getting a quote with the dates you've selected contact us so we can check the avail ...
From $581 per night (USD)Expedia
From $191 per night (USD)VRBO
Dog-friendly family home with WiFi, central AC, private W/D - close to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
21 Palms Unit A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $191 per night (USD)VRBO
From $1082 per night (USD)Expedia
Our Great Escape by Duncan Real Estate
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful luxury pool home is one of a kind in a secluded prestigious North end location directly on the canal with ...
From $1082 per night (USD)Expedia
From $808 per night (USD)VRBO
AMI Luxury! Spa Suite, Pool & Walkability
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Crush by Anna Maria Island Accommodations 111 Cedar Ave, Anna Maria, Florida VR21-000015 Welcome to Blue Crus ...
From $808 per night (USD)VRBO
From $2267 per night (USD)Expedia
Luxury Beachfront on the Sand of Gulf of Mexico
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Photos Updated January 2025! Sunnyside Escape is a newly built luxury home situated on the famous white sand gulf beach ...
From $2267 per night (USD)Expedia
From $1169 per night (USD)VRBO
Beachfront Bliss – 4 King Bedrooms, Golf Cart & Shuffleboard
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Luxury 4-King Bedroom Beachfront Home with Golf Cart & Shuffleboard Wake up to the sound of waves and end your day with ...
From $1169 per night (USD)VRBO
From $347 per night (USD)Expedia
Angel Fish Cottage, Sweet 2 BR 1 B, Private Pool, Steps to Gulf and Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Newly Renovated Angel Fish Cottage with new flooring, beds and furniture. Located on the north, quiet end of Anna Maria ...
From $347 per night (USD)Expedia
From $368 per night (USD)VRBO
Caribbean Reef! Cozy Pool Home Near Gulf!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Caribbean Reef by AMI Locals Holmes Beach Villa with Private Pool, Patio, and Steps to the Beach VRC18-000084 Welco ...
From $368 per night (USD)VRBO
From $687 per night (USD)Expedia
Canalfront Home, Saltwater Pool, Near Beaches and Shopping - Sunrise Shore
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Sunrise Shore by AMI Locals 300 North Shore Dr, Unit A (North), Anna Maria, FL 34216 VPR16-000431 Welcome to Sunrise S ...
From $687 per night (USD)Expedia
From $749 per night (USD)VRBO
Luxury Home with Private Pool and Spa! Short Walk to Beach! - Mojito Splash
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Mojito Splash by AMI Locals Holmes Beach Luxury Waterfront Home with Pool and Outdoor Entertaining VRC18-000068 Welco ...
From $749 per night (USD)VRBO
From $402 per night (USD)Expedia
Hav'Anna Holiday: 2 Blocks to Beach! North End! Private Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Hav'Anna Holiday by Anna Maria Life Vacation Rentals 211 Periwinkle, Anna Maria, FL 34217 What You'll Love About This H ...
From $402 per night (USD)Expedia
From $871 per night (USD)VRBO
Park n Chill: North End, Steps to Beach, West of Gulf, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Park n Chill by Anna Maria Life Vacation Rentals 117 Park Ave, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $871 per night (USD)VRBO
From $1507 per night (USD)Expedia
Large Canal Front Family Rental on Anna Maria with Pool, Dock & Mini Golf!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
Serenity Beach by AMI Locals Home in Anna Maria, Florida VR16-000464 Welcome to Serenity Beach! This stunning canal-f ...
From $1507 per night (USD)Expedia
From $819 per night (USD)VRBO
Brand New Putting Green! Close to beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Marlin by AMI Locals Home in Anna Maria, FL Highlights • 10-minute walk from the Beach • Private Pool and Hot Tub ...
From $819 per night (USD)VRBO
From $510 per night (USD)Expedia
Beautiful Bungalow with Private Pool and Spa, just Steps to the Beach! - Mermaid
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Mermaids Watch by Anna Maria Island Accommodations 207 69th Street, Unit A, Holmes Beach, Florida VRC18-000086 Welcome ...
From $510 per night (USD)Expedia
From $282 per night (USD)VRBO
Best location on the island. Private dock, steps to Anna Maria Beach and Pier
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
From our private dock you can watch the sunset, drop a fishing line, watch manatees, or launch your paddle board or kaya ...
From $282 per night (USD)VRBO
From $334 per night (USD)Expedia
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay-
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Newly Renovated Boathouse Cottage is ready to welcome guests. New flooring, new beds, new furniture. Located on the we ...
From $334 per night (USD)Expedia
From $440 per night (USD)VRBO
2 MIN WALK TO GULF BEACHES, LG HEATED POOL, XLG LANAI - GAS GRILL and More
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Whispering Palms Villa at North Beach Village is a bright and sunny, tastefully decorated beach style townhouse located ...
From $440 per night (USD)VRBO
From $454 per night (USD)Expedia
Beautiful Bungalow with Private Pool! Close to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Day Break Bungalow by AMI Locals Anna Maria Island Luxury Vacation Home VRC19-000140 Experience the ultimate beachsid ...
From $454 per night (USD)Expedia
From $335 per night (USD)VRBO
Big Seader in Anna Maria
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
**ASK ABOUT LAST-MINUTE DEALS! Enjoy a simple, old-fashioned seaside vacation in this adorable duplex west of Gulf Driv ...
From $335 per night (USD)VRBO
From $617 per night (USD)Expedia
Canal-front Gem w/ Pool & Hot Tub in Anna Maria
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to the sandy shores of Anna Maria Island at ‘Easy Breezy’, a recently renovated canalfront vacation rental cottag ...
From $617 per night (USD)Expedia
From $1137 per night (USD)VRBO
Summer Discounts! Steps from the Beach! Walk to Bean Point! Pool/spa! Golf Cart
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Have the best of both worlds with the bay & the gulf beaches at this new 4 bed/3.5 bath luxury home. Enjoy the quiet, l ...
From $1137 per night (USD)VRBO
From $1398 per night (USD)Expedia
Three Little Birds - Luxury Gulf-View Home w/ Heated Pool & Steps to Bean Point
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Three Little Birds! On Anna Maria Island (Anna Maria, FL) Experience Three Little Birds – A Luxurious Coasta ...
From $1398 per night (USD)Expedia
From $379 per night (USD)VRBO
Private pool, 3 bedroom on Anna Maria Island, only minutes to the beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The comfort in Egret's Landing is stunning. The home is fully equipped with everything you need like a full kitchen with ...
From $379 per night (USD)VRBO
From $431 per night (USD)Expedia
3 bedroom on Pine in Anna Maria Island, private pool and PET friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Seashell is 3 bedroom 2 bath second story condo that is set up like a single family home. It features wood floors, a kin ...
From $431 per night (USD)Expedia
From $495 per night (USD)VRBO
Steps to the beach! PRIVATE HEATED POOL w covered lanai. Central location.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Two minute walk to beach access at the end of our street! PRIVATE heated pool. Air conditioned 2 bedroom 2 bath home. P ...
From $495 per night (USD)VRBO
From $508 per night (USD)Expedia
Two minute walk to beach! PRIVATE HEATED POOL w covered lanai. Great location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Two minute walk to beach access at the end of our street! PRIVATE heated pool. Air conditioned 2 bedroom 2 bath home. P ...
From $508 per night (USD)Expedia
From $3226 per night (USD)VRBO
Beachfront Home | Pool + Spa | Games | Ocean Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the exclusive Beachfront Bliss - a custom-built luxury vacation home nestled directly on a sandy beach. This ...
From $3226 per night (USD)VRBO
From $1285 per night (USD)Expedia
Paradise Blu by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Paradise Blu! Your luxury vacation awaits in this newly built 4 bedroom, 4.5 bath treasure. Perched in the mo ...
From $1285 per night (USD)Expedia
From $1000 per night (USD)VRBO
Beach Escape! Luxury Home with Pool, Spa, Rooftop Deck and Walk to Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Beach Escape by AMI Locals 789 Jacaranda Rd, Anna Maria, FL, 34216 VR18-000090 Welcome to Beach Escape, a five bedr ...
From $1000 per night (USD)VRBO
From $673 per night (USD)Expedia
1 block to the beach! Adorable bungalow with Pool and Spa, great for families!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Highlights • 3-minute walk from the Beach • 2-minute walk from Pine Ave • Private Pool and Hot Tub • Dog friendly w ...
From $673 per night (USD)Expedia
From $337 per night (USD)VRBO
Hidden Oasis - DIRECT BEACHFRONT DUPLEX - 1BR/1BA Anna Maria - By Island Real Es
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Hidden Oasis is beautiful 1-bedroom 1-bathroom duplex that’s perfect for an island stay. The décor will make you feel ri ...
From $337 per night (USD)VRBO
From $493 per night (USD)Expedia
BEST LOCATION! NORTH END OF ANNA MARIA, FL , STEPS TO BEACH & DINING - UNIT A
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Location, Location, Location! The home located on the very desirable quiet north end of Anna Maria, Florida . This charm ...
From $493 per night (USD)Expedia
From $882 per night (USD)VRBO
Luana Breeze close to AMI beach. Pool, Spa, Tiki Hut.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to "Luana Breeze" located at 208 68th Street, Holmes Beach. Find ease and relaxation the moment you arrive, this ...
From $882 per night (USD)VRBO
From $374 per night (USD)Expedia
Briney Breezes - Old Florida living with modern comforts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
308 TARPON ST. BRINEY BREEZES This three bedroom, three bath dream home is the perfect way to experience all that Anna M ...
From $374 per night (USD)Expedia
From $425 per night (USD)VRBO
Eclectic North end AMI home with Private pool on Canal!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Right on the water with canal access in the back yard. Private swimming pool overlooks the water.and Ample Parking for y ...
From $425 per night (USD)VRBO
From $247 per night (USD)Expedia
Updated bayside condo with heated pool - across the street from the beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
South Bay Inn 1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $247 per night (USD)Expedia
From $523 per night (USD)VRBO
Beautifully Remodeled Home with Private Pool and Spa! Near beach & shopping!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Last Resort by AMI Locals Holmes Beach Waterfront Retreat with Pool & Hot Tub VRC19-000160 Welcome to Last Resort, th ...
From $523 per night (USD)VRBO
From $628 per night (USD)Expedia
Blue Heron Beach House: Canal-front pool home near Pine Ave.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Blue Heron Beach House! This beautiful, newly renovated home is located in the heart of Anna Maria on a deep ...
From $628 per night (USD)Expedia
From $753 per night (USD)VRBO
Funky Beach Farmhouse: Beautiful Bay views, heated pool, hot tub, lounge area
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
We invite you to come enjoy your vacation at the Funky Beach Farmhouse! This professionally decorated beach house is sur ...
From $753 per night (USD)VRBO
From $564 per night (USD)Expedia
Coconut Cottage by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Coconut Cottage! This beautiful 3-bedroom, 2-bathroom cottage has 1,620 square feet of elevated living space ...
From $564 per night (USD)Expedia
From $266 per night (USD)VRBO
Stylish bayside condo with WiFi & pool - close to the beach & restaurants
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
South Bay Inn 3 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $266 per night (USD)VRBO
From $579 per night (USD)VRBO
Beach House w/ pool on the north end of AMI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming 3 bedroom elevated home with a private pool at 123 Hammock Road in Anna Maria which is only 2 short blocks to t ...
From $579 per night (USD)VRBO
From $921 per night (USD)VRBO
Anna Maria Northshore beauty W/ Private Pool. 1 block from Anna Maria Beach!!!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Enjoy The Good Life! In our unforgettable Beach Home. The property was built to standards for guests who demand the very ...
From $921 per night (USD)VRBO
From $596 per night (USD)Expedia
Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 110 is ...
From $596 per night (USD)Expedia
From $520 per night (USD)VRBO
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 109G is ...
From $520 per night (USD)VRBO
From $563 per night (USD)Expedia
Adorable Cottage moments to beach w/ pool, beach gear, bikes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Escape to Cotta ...
From $563 per night (USD)Expedia
From $501 per night (USD)VRBO
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 110B is ...
From $501 per night (USD)VRBO
From $546 per night (USD)Expedia
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Sassy Seagull C ...
From $546 per night (USD)Expedia
From $398 per night (USD)VRBO
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 107A is ...
From $398 per night (USD)VRBO
From $406 per night (USD)Expedia
Anna Maria Beach Cottage 109A -Old-Florida beach cottage, steps to the beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 109A i ...
From $406 per night (USD)Expedia
From $373 per night (USD)VRBO
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 107G is ...
From $373 per night (USD)VRBO
From $539 per night (USD)Expedia
Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 110A i ...
From $539 per night (USD)Expedia
From $641 per night (USD)VRBO
Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Flirty Flaming ...
From $641 per night (USD)VRBO
From $541 per night (USD)Expedia
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below! Cottage 110G is ...
From $541 per night (USD)Expedia
Click For PricingVRBO
Newly Updated Condo with Pool, Near the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea You Soon by AMI Locals Holmes Beach Luxury Condo Near Beach and Trolley VRC22-000162 Welcome to Sea You Soon, a b ...
Click For PricingVRBO
From $675 per night (USD)Expedia
Charming cottage with heated pool, tropical landscaping in prime location.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Starfish Cottage has been recently renovated while maintaining all the charm of an old Florida Key West style bungal ...
From $675 per night (USD)Expedia
From $176 per night (USD)VRBO
Ground-floor duplex with fast WiFi, central AC & grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
21 Palms Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $176 per night (USD)VRBO
From $290 per night (USD)Expedia
Beach House Anna Maria Island, FL - 1 block to beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this beautiful home in North Beach Village on Anna Maria Island, where coastal charm and exceptional privacy ...
From $290 per night (USD)Expedia
From $366 per night (USD)VRBO
Dog-friendly home with amazing backyard, pool, spa, putting green & game room
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Getaway on Gladiolus Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $366 per night (USD)VRBO
From $1307 per night (USD)Expedia
Impressive Luxury Home steps to the Beach! Great Pool and Spa! - Grande Haven
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 16
Grande Haven by AMI Locals Home in Anna Maria, Florida VR18-000049 Highlights • 2-minute walk to the beach • Private ...
From $1307 per night (USD)Expedia
From $284 per night (USD)VRBO
Coconut Bayou by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Bayou 5C! With a prime location the north side of Pine Avenue on Anna Maria Island. The Bayou 5C is the ...
From $284 per night (USD)VRBO
From $506 per night (USD)Expedia
Beach Pearl - Private Pool Home - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Just a short stroll from Gulf of Mexico beaches, Anna Maria vacation rental “Beach Pearl” offers a luxurious getaway exp ...
From $506 per night (USD)Expedia
From $1525 per night (USD)VRBO
Tern Key - Luxury Canal-Front Home w/ Heated Pool, Spa, Dock & Near Bean Point
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Tern Key! On Anna Maria Island (Anna Maria, FL) Experience Tern Key – A Luxury Canal-Front Retreat with Heat ...
From $1525 per night (USD)VRBO
From $1006 per night (USD)Expedia
Modern Beach House with excellent location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Direct Beach Access, fully renovated beach house. Main floor master suite that walks out to large outdoor living space. ...
From $1006 per night (USD)Expedia
From $369 per night (USD)VRBO
Private Heated Pool and Close to the beach with beach gear and Dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This nicely appointed 2 bedroom, 2 bath ground floor home with Private Pool is located one very short block to the beaut ...
From $369 per night (USD)VRBO
From $1006 per night (USD)Expedia
Pink Palm: Dog-friendly, 6-bedroom, 3-min walk to beach!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Pink Palm is one of the most impressive vacation rentals on Anna Maria Island! The home is located just a half a block a ...
From $1006 per night (USD)Expedia
From $1103 per night (USD)VRBO
Still Waters Beach House- A north end tropical getaway.
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Still Waters Beach House! Come rest and be refreshed in one of the most family friendly and spacious (3600+ S ...
From $1103 per night (USD)VRBO
From $837 per night (USD)Expedia
AMI Retreat! Pool, Spa, Ping Pong and Walk to Holmes Beach
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Seas the Day by AMI Locals 7204 Palm Dr, Holmes Beach, FL, 34217 VRC22-000025 Welcome to Seas the Day, a three level ...
From $837 per night (USD)Expedia
From $486 per night (USD)VRBO
BEST LOCATION! NORTH END OF ANNA MARIA, FL , STEPS TO BEACH & DINING , UNIT B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Location, Location, Location! The home located on the very desirable quiet north end of Anna Maria, Florida . This charm ...
From $486 per night (USD)VRBO
From $579 per night (USD)Expedia
Fun in the Sun 😎 | Gulf front, steps to the sand, 4-bed with spectacular views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Recently Updated Vintage Island Beach Front home has 4 sleeping rooms and 2 bathrooms. Enjoy the charm of yesterday in t ...
From $579 per night (USD)Expedia
From $602 per night (USD)VRBO
Anna Maria Escape! Pool, Spa, and Canal Views - Our Tern
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our Tern by Anna Maria Island Accommodations 111 Tern Dr, Anna Maria, Florida 34216 VR22-000023 Welcome to Our Tern, a ...
From $602 per night (USD)VRBO
From $1733 per night (USD)Expedia
Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak, SUPs & MORE
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to the Rum Cove Experience! This magical home is a one-of-a-kind oasis 🌴 on a one-of-a-kind island located ri ...
From $1733 per night (USD)Expedia
From $707 per night (USD)VRBO
Over the Moon - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
“Over the Moon” located on the North end of Anna Maria is an adorable 3 bedroom, 2 bathroom cottage that spaciously acco ...
From $707 per night (USD)VRBO
From $417 per night (USD)Expedia
Anna Maria Home with Private Saltwater Pool, Close to Beach! - Casa Azul
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Casa Azul by AMI Locals Holmes Beach Vacation Home VRC21-000108 Welcome to Casa Azul, a breathtaking tropical retreat ...
From $417 per night (USD)Expedia
From $454 per night (USD)VRBO
Lovely island home - 1 block to Pine Street, 2 dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spring Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $454 per night (USD)VRBO
From $290 per night (USD)Expedia
Beach n It: Dog Friendly, Pool, Convenient to all of AMI by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beach n It by Anna Maria Life Vacation Rentals 410 Bay Palms Dr., Holmes Beach, FL 34217 What you'll love about this ho ...
From $290 per night (USD)Expedia
From $1278 per night (USD)VRBO
Banyan Beach: Steps to Beach, Pool, Game Room, Putting Green by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Banyan Beach by Anna Maria Life Vacation Rentals 104 Beach Ave, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $1278 per night (USD)VRBO
From $1501 per night (USD)Expedia
Snook Lookout: Canal Home, Pool, Game Room, Putting Green by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Snook Lookout by Anna Maria Life Vacation Rentals 211 Oak Ave, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $1501 per night (USD)Expedia
From $954 per night (USD)VRBO
Luxury 4-Bedroom Home Near Beach with Pool & Spa at Under The Sea, Anna Maria!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Under The Sea by AMI Locals 118 Peppertree Lane, Anna Maria, Florida VR17-000055 Welcome to Under The Sea! This stun ...
From $954 per night (USD)VRBO
From $907 per night (USD)Expedia
Stunning 5 Bedroom Luxury Home, Pool and Spa, Beach Views! - Coastal Queen
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Coastal Queen by AMI Locals 791 Jacaranda Rd, Anna Maria, Florida 34216 VR18-000091 Welcome to Coastal Queen, a w ...
From $907 per night (USD)Expedia
From $823 per night (USD)VRBO
Amazing home with WATERSLIDE! One Block off beach! Life is Just Beachy here!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to Just Beachy on beautiful Anna Maria Island! Have the trip of a lifetime at this beautifully appointed 6 bedro ...
From $823 per night (USD)VRBO
From $895 per night (USD)Expedia
Mainsail Beach Inn 2 Bedroom Beach Facing Unit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The furnishings and appointments in your private Holmes Beach vacation rental are elegant, fresh and bright. The two bed ...
From $895 per night (USD)Expedia
From $932 per night (USD)VRBO
Mainsail Beach Inn 2 Bedroom Beach Front Unit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The furnishings and appointments in your private Holmes Beach vacation rental are elegant, fresh and bright. The two bed ...
From $932 per night (USD)VRBO
From $1040 per night (USD)Expedia
Mainsail Beach Inn 3 Bedroom Beach Front unit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Our spacious three bedroom beachfront retreats offer up to 1,627 square feet of fully furnished living space, perfect fo ...
From $1040 per night (USD)Expedia
From $878 per night (USD)VRBO
Mainsail Beach Inn 3 Bedroom Townhouse
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The interior decor in your private Holmes Beach vacation rental is elegant, fresh and bright. These three bedroom, three ...
From $878 per night (USD)VRBO
From $1691 per night (USD)Expedia
Gulfview Estate: Beachfront luxury home with sweeping Gulf views
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Gulfview Estate, your exquisite beachfront retreat where luxury meets tranquility. This stunning 5-bedroom, 4 ...
From $1691 per night (USD)Expedia
From $259 per night (USD)VRBO
Island Escape with Pool and Balcony! Near the Beach and Dining - Two Sisters
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Two Sisters by Anna Maria Island Accommodations 6319 Gulf Dr, Holmes Beach, FL 34217 Escape to Two Sisters, an adorabl ...
From $259 per night (USD)VRBO
From $274 per night (USD)Expedia
\"La Casita\" Beautiful, Elegant Florida Cottage, 1 Minute Walk to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in beautiful tropical landscaping, this 2 bed, 2 bath beach cottage vacation rental blends simple elegance with ...
From $274 per night (USD)Expedia
From $705 per night (USD)VRBO
Mangrove Mojito: Canal, Pool, Hot Tub, Dock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Gorgeous and spacious is this 4 Bedroom/3 Bath Home in a desirable north-end location, just steps to Historic Pine Avenu ...
From $705 per night (USD)VRBO
From $761 per night (USD)VRBO
3 bed / 2 bath with heated pool and spa; private dock on canal
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to MANATEE SANCTUARY, our spacious 3 Bed / 2 Bath home with backyard canal, and private heated pool and spa (hot ...
From $761 per night (USD)VRBO
From $484 per night (USD)VRBO
Anna Maria Island Rentals - Beach Front - \"Angels Envy\" -Rod & Reel Pier Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
First, Anna Maria Island is broken up into 3 cities, Anna Maria, Holmes Beach and Bradenton Beach. The City of Anna Mar ...
From $484 per night (USD)VRBO
From $504 per night (USD)Expedia
8 Palms: Gorgeous heated pool and lounge area, with putt-putt!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
8 palms is a beautiful 3 bedroom 2 bath home on the North end of Anna Maria Island. The property is newly renovated and ...
From $504 per night (USD)Expedia
From $685 per night (USD)VRBO
Beach N Bay 206 by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Beach N Bay 206! Pool COOLING for hot summer days! A honeymooners delight or a couple's retreat! ...
From $685 per night (USD)VRBO
From $680 per night (USD)Expedia
The Sunset Place- Unbeatable location. Gorgeous Sunsets. Updated Coastal Gem
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
<p>A short distance from sailing, scuba diving, and more, this family-friendly vacation home lets you experience it all. ...
From $680 per night (USD)Expedia