Book Direct & Save - No Booking Fees
Key Amenities
About this property
Waterfront Pool Retreat + Dock & Boat Lift + Golf Cart | Beach BlissWelcome to Beach Bliss, your waterfront escape on Anna Maria Island — where relaxed luxury, boating adventures, and effortless island living come together for an unforgettable stay.This beautifully designed 4-bedroom,...
Key Amenities
About this property
Casa Amiga by Beach Retreats Vacation Rentals 144 Crescent Dr. Anna Maria, FL 34216 City of Anna Maria | 4 Bedrooms | 4.5 Bathrooms | Sleeps 10 | Heated Pool + Jacuzzi | Rooftop Deck | Shared DockLuxury Island Living Near Bean Point Welcome to Casa Amiga, a beautifully designed 4-bedroom, 4.5-bath...
Key Amenities
About this property
Bayfront Pool Retreat + Walk to Pine Ave + Golf Cart | TripletailWelcome to Tripletail, your bayfront escape on the coveted north end of Anna Maria Island — where peaceful waterfront views, walkability to Pine Avenue, and resort-style outdoor living come together for an unforgettable stay.Perfectly...
Featured review
Beautiful, outstanding home with unbelievable views from every window! The water is right outside your door. Plus there's a hot tub out back and a pool out front. It was a very memorable trip that I'll...
Key Amenities
About this property
Crosswind Cottage 312 A 61st Street, Holmes Beach, FL 34217 VRC19-000277 3 Bedrooms | 2.5 Bathrooms | Sleeps 10 | Heated Pool | Game Room | Elevator This home can park up to 3 vehicles Elevator Quiet hours at 10p-7a: please respect neighborsWelcome to Crosswind Cottage, a spacious island...
Featured review
Very nice house, everything worked. Two things that were not so wonderful- The pool gets barely any sun coverage daily. There is NO easy way to walk to the ocean. Houses block off and no entry unless...
Key Amenities
About this property
Location, Location, LocationStaying near the Holmes Beach public beach means you get the best of the island without the hassle:Easy, stress-free beach access (no long walks or parking) Nearby public amenities like restrooms, showers & lifeguards Walk to restaurants, cafes & beach...
Why Choose FloridaRentals.com?
No Booking or Service Fees
Save up to 25% compared to other websites - no hidden costs.
Connect Directly with Hosts
Book with confidence and get the best rates.
Florida's #1 Vacation Rental Site
Trusted by millions - your go-to for the perfect Florida getaway.
Key Amenities
About this property
Just Beachy – Your Luxury Island Retreat on Anna Maria Island 128 49th Street Holmes Beach FL 34217 VRC21-000019 4 Bedrooms + nanny suite | 6 Bathrooms | Sleeps 10 | Heated Pool & Hot Tub | This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighborsEscape...
Featured review
We spent Thanksgiving week at Sunset and Sand and it delivered on all our expectations. The home is clean, beautifully decorated and functional. The kids absolutely loved the heated pool and Spa and Its...
Key Amenities
About this property
Vitamin Sea by Beach Retreats Vacation Rentals 146 Crescent Dr, Anna Maria, FL 34216Welcome to Vitamin Sea, a stunning 5-bedroom, 5-bath luxury retreat located on the coveted north end of Anna Maria Island, just a 10-minute stroll to Bean Point Beach. With a private dock, heated saltwater pool and...
Featured review
Vitamin Sea exceeded all expectations for our week's vacation for our family of 12. Location was perfect for daily visits to both sides of the island. House is stunning and fully equipped for swimming,...
Key Amenities
About this property
Shangri-La | Gated Bean Point Estate — Anna Maria Island’s Most Coveted LocationWelcome to Shangri-La, a rare and extraordinary beachfront estate perched on the exclusive tip of Anna Maria Island at Bean Point — widely considered the island’s most breathtaking and sought-after...
Key Amenities
About this property
Oasis by the Beach by Beach Retreats Vacation Rentals 202 69th St, Holmes Beach, FL 34217 VRC17-000120 5 Bedrooms | 4 Bathrooms | Sleeps 10 | Heated Pool & Hot Tub This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Book with confidence: No cancellation...
Featured review
Another family and ourselves rented the property. We found it very clean and equipped to a high standard. The pool and jacuzzi were great and well used especially by the kids. The management company were...
Key Amenities
About this property
Surf Side Beach House – Gulf Views Hosted by Beach Retreats Vacation Rentals 6605 Gulf Drive, Holmes Beach, FL 34217 VRC19-00290 4 Bedrooms | 4.5 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Welcome...
Featured review
The property was great, and worked really well with our family-which includes a 4 year old and a 9 month old, so having the bedrooms in different areas and private baths, made everything much easier. Centrally...
Key Amenities
About this property
Luxury Coastal Retreat + Elevator + Complimentary Golf Cart | Serendipity DeuxWhere luxury meets effortless island living, you’ll find Serendipity Deux — a beautifully designed 4-bedroom retreat offering refined interiors, premium beach access, and an unbeatable Anna Maria Island location.From...
Key Amenities
About this property
True Beachfront Escape + Elevator + Hot Tub + Golf Cart | Serendipity Anna MariaWelcome to Serendipity, your pet-friendly beachfront sanctuary on the coveted north end of Anna Maria Island — where quiet mornings, spectacular sunsets, and the rhythm of the Gulf create the perfect island escape.Perfectly...
Key Amenities
About this property
Turtle's Bay by Beach Retreats Vacation Rentals 306 Clark Dr Unit B, Holmes Beach, Anna Maria Island VRC17-000006 3 Bedrooms | 3.5 Bathrooms | Sleeps 6 | Heated Pool ​​​​​​​ Pet Friendly This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighborsDog...
Featured review
Visiting Anna Maria Island was amazing!! The weather was beautiful and the home was beautiful too!! I would definitely come back to visit this area.
Key Amenities
About this property
110 11th Street South - Bradenton Beach - FL 34217No cancellation fees! Cancel 60+ days before arrival → Full refund Cancel within 60 days → No refund Extended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable $500 deposit due at booking; balance due 60...
Featured review
The house was beautiful, lots of space to spread out with a family of 12. Location was perfect, beach on one side and bay on the other. Had everything we needed for cooking, pool, and relaxing. Pool was...
Key Amenities
About this property
Beachfront Luxury + Pool Deck + Complimentary Golf Cart | Cloud 9Welcome to Cloud 9, a stunning beachfront retreat where modern luxury meets relaxed coastal living. Perfectly positioned on the quiet north end of Anna Maria Island, this beautifully designed 5-bedroom home offers everything your group...
Featured review
This home was perfect for our family vacation- great views, clean, well stocked, we will definitely be back! Thank you!
Key Amenities
About this property
Private Pool Oasis + Beach Volleyball Court + INCLUDED Golf Cart | Fanta-SeaEscape to Fanta-Sea, your private tropical retreat on the coveted north end of Anna Maria Island — where backyard fun, beachside relaxation, and effortless island exploring come together.Step through your back gate...
Key Amenities
About this property
Welcome to Breathe Inn, your island escape where the sea breeze is plentiful and the relaxation comes naturally. This beautifully renovated 5-bedroom, 3.5-bath duplex with 2 kitchens invites you to exhale and settle into vacation mode. With two fully private units under one roof, it's the perfect...
Featured review
Wonderful property and perfect for families with kids. The house was clean, well appointed with everything you could possibly need, and comfortable for everyone. The pool was always clean and well maintained....
Key Amenities
About this property
306 67th Street Unit B Holmes Beach, FL 34217 VRC Caribbean Surf by Beach Retreats Vacation RentalsHolmes Beach, Anna Maria Island 3 Bedrooms | 2 Bathrooms | Sleeps 6 | Private Heated Pool | Pet-FriendlyYour Anna Maria Island Bungalow Retreat Welcome to Caribbean Surf, a bright and inviting...
Featured review
The home has recently been redone, very comfortable and accomodating with a nice sitting deck and new pool. We had a short walk to a beach access and the location allowed us to visit the north island area...
Key Amenities
About this property
Absolutely beautiful monthly rental in highly sought after Holmes Beach on Anna Maria Island. If you are interested in dates blocked on the calendar, please message me. This 100% updated home has everything from a large heated pool, outdoor shower, lush mature landscaping, completely furnished inside...
Featured review
WOW! I can not say enough about the wonderful stay we had. The house was beautiful and stocked with everything a family would need and the location is perfect. Short walk to beach and Pine St. restaurants...
Key Amenities
About this property
Sandcastle – Beachside Escape with Heated Pool, Golf Cart & Island Adventure Gear3 Bedrooms | 2.5 Bathrooms | Heated Pool | Golf Cart | Bikes | Paddle Boards | Kayaks | Steps to the BeachWelcome to Sandcastle, your perfect Anna Maria Island beach retreat. Ideally located just across...
Distance to beach: 50 feet to across the street
Key Amenities
About this property
Key Lime Cottage | Hot Tub + Fenced Yard + Golf Cart | North Shore Retreat 3 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet Friendly | Private Hot Tub | 6-Passenger Golf CartWelcome to Key Lime Cottage, a charming north-end escape tucked along coveted North Shore Drive on Anna Maria Island. Just a short...
Key Amenities
About this property
Beachfront boho escape on Anna Maria Island NEW heated Gulfside pool + hot tub with sunset views 4BR layout with private cottage for extra space & privacy Steps to the sand + paddle boards, bikes & INCLUDED 6-passenger golf cart Serene north-end location — the island retreat guests...
Key Amenities
About this property
Please reach out for a quote or if you have any questions, we respond quickly. Welcome to Sol Y Mar! This bright, newly refreshed 3 Bedroom beach house oasis features the perfect mix of modern decor mixed with touches of mid-century inspired furnishings and original terrazzo floors. Guest will love the...
Key Amenities
About this property
VRC 107 78th street Holmes Beach 34217To Book Directly please visit: /chasing-wavesIf you are looking for something other than a 7 night stay, please give our office a call and we will do our very best to accommodate you! Beach Retreats Reservations Team:“You are vacationing in...
Featured review
We had a great week in this unit and were pleased with many things it had. I would stay there again without hesitation. A FEW issues though with the unit. A fee of $69 for linens. We rented for 10 days...
Key Amenities
About this property
Welcome to Hidden Treasure Unit B! VRC25-000106 .1 Miles to Holmes Beach Shared Heated Pool Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! Fully stocked kitchen for all your favorite home-cooked meals High-speed Wi-Fi included Smart lock for Self Check-in...
Key Amenities
About this property
Welcome to Sweet Home Anna Maria! Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! Private Heated Pool & Hot Tub with Plenty of Seating for the Whole Family! Game Room with Ping Pong, Dart Board, Extra Fridge & Bathroom Every Bedroom has an Ensuite Bathroom!...
Key Amenities
About this property
2 bedroom 2 bath 1000 square feet condo with a beachfront view of the Gulf of Mexico on the quiet, peaceful Anna Maria Island. Walking distance to many restaurants and bars. 30 minutes away from the Sarasota/Bradenton airport. Free trolley to go anywhere on the island.
Featured review
Wonderful stay, quiet neighborhood, location is amazing - the beach is half a block away! Shopping including restaurants and grocery store close by, within walking distance, too. This is a great family-friendly...
Key Amenities
About this property
Welcome to Mermaid Sunset! VRC16-000276 Private Heated Pool/ Spa 200 steps to Holmes Beach Beach Chairs & Wagon Available for use 1 Mile to Pine Ave. Fishing, Shopping, Restaurants, and more High speed Wi-Fi, Smart lock for Self Check-in Pool Heat included with rental Welcome...
Key Amenities
About this property
Discover The Salty Fern, a stunning 3-bedroom, 2-bathroom house on Anna Maria Island's desirable North End. This stylish coastal retreat boasts a private pool, ideal for relaxing after a day at the beach. Enjoy easy access to pristine beaches, water activities, and the charm of Anna Maria. The space Quiet...
Key Amenities
About this property
Welcome to Mermaid Sunrise! VRC16-000276 Private Heated Pool/ Spa 200 steps to Holmes Beach Beach Chairs & Wagon Available for use 1 Mile to Pine Ave. Fishing, Shopping, Restaurants, and more High speed Wi-Fi, Smart lock for Self Check-in *Pool heat is unavailable as of 4/7/2026...
Key Amenities
About this property
Welcome to paradise- AMI VILLA! When you come to Anna Maria Island for vacation, make this charming Mediterranean beach 3 bedroom & 3 bath villa your home away from home! With much to offer, this home will have your family wanting to return to Anna Maria Island year after year.Features include: -3...
Featured review
This house is perfect for a large family. 3 bedrooms and 3 full baths. Close to the beach and provides everything you need! Chairs, umbrellas and a wagon to use to transport everything. Even an ice...
Key Amenities
About this property
Steps to Beach + Heated Pool + Putting Green + Golf Cart | WavesWelcome to Waves, your beautifully remodeled coastal retreat on Anna Maria Island — where modern luxury, effortless beach access, and resort-style outdoor living create the ultimate island escape.Perfectly positioned just across...
Key Amenities
About this property
Welcome to Hidden Treasure Unit A! VRC18-000124.1 Miles to Holmes Beach Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! Fully stocked kitchen for all your favorite home-cooked meals Shared Heated Pool High-speed Wi-Fi included Smart lock for Self Check-in...
Key Amenities
About this property
Welcome to Ocean Star! .01 Miles to Amazing Gulf Coast Beaches Private Heated Pool/Spa with Outdoor Seating & BBQ Beach Equipment Available for Use Every Bedroom Has a Private Bathroom Fully stocked kitchen for all of your favorite home-cooked meals High-speed Wi-Fi, Smart lock for Self...
Key Amenities
About this property
Beachcomber showcases spacious decking and a bright, open-concept living, dining, and kitchen area, radiating coastal luxury and charm. The main bedroom features a sumptuous king-size bed and a stylish en-suite bathroom with a soaking tub and a shower, while the second bedroom can be configured as either...
Key Amenities
About this property
Welcome to Sea Site Unit B! 100 Steps to the World Class Beaches of Anna Maria Island Close to Restaurants, Shopping, and More Private Patio for Beach Equipment and Grilling King, King, & Two Full Beds High speed Wi-Fi & Smart lock for Self-Check-inWelcome, too Sea Site Retreat Unit...
Key Amenities
About this property
Welcome to Sea Site Unit A! 100 Steps to the World Class Beaches of Anna Maria Island Close to Restaurants, Shopping, and More Water Views from Balcony King, King, & Two Full Beds High speed Wi-Fi & Smart lock for Self-Check-inWaking up to a view of the coast with your morning cup...
Key Amenities
About this property
Welcome to "Down On The Island" the perfect beach destination for your next family getaway! .01 Miles to the World Class Beaches of Anna Maria Island Nearby Park with Basketball, Playground, Kayak Launch Fully Stocked Kitchen for Home-Cooked Delights Seamless Arrival with Fast Wi-Fi...
View on map
List view