58,368 properties available

Located in Holmes Beach, Florida, United States. Holmes Beach private home - 2 blocks to the beach! Just a stone's throw from the Gulf, this clean and comfortable 2 bedroom / 2 bathroom cottage is the perfect place to get away and enjoy "Island" life. Quiet peaceful island location, and less than 3/10 of a mile to the beach. Lovely oak kitchen for the cook in the family. One car garage with full size washer and dryer. Sit back and catch up on your favorite shows or movies on the large, flat screen t. v. Master bedroom features a roomy king size bed, while the guest room has 2 twins as well as a Queen sleeper in the living room. Enjoy the large screened patio, and the beautiful green yard. Prices shown are based on four person occupancy. Additional persons staying in the unit may be considered additional occupants and subject to additional rental fees being charged and/or application and approval process if the community is governed by association rules and regulations. Your rental Agent must be advised of all addit

Located in Holmes Beach, Florida, United States. Emerald Bay managed by Beach Retreats 306 (A) Clark St - Holmes Beach - FL 34217VRC17-000006You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations made on or less than 60 days in advance of check-in, your reservation is non-refundable.Written notice is required to cancel a reservation; an email from the address associated with the reservation is acceptable as written notice.For canceled reservations with a check-in date equal to or less than 60 days away: We will open the property back up to the rental market and if the property re-rents we will refund the guests the rental rate minus the $495 processing fee and any price differential.If Guest needs to shorten their stay or change to a different property, the normal cancellation policy applies. No changes are permitted during the stay.

Located in Holmes Beach, Florida, United States. 1.5 Blocks to Gulf Beaches, Private Heated Pool - No Bad Days No Bad Days by Anna Maria Island AccommodationsHome in Holmes Beach, FL VRC18-000057Welcome to No Bad Days, an inviting ground-level vacation home that is just a three-minute walk to the sugar-white sands of Holmes Beach! This four-bedroom, three-bath getaway has a stunning backyard, complete with a dazzling pool featuring a built-in table and a soothing in-ground spa. Lounge on the patio's sunbeds, fire up the BBQ grill for al fresco feasts and rinse off under the outdoor shower before dining at the outdoor table.Highlights • Less than a 5-minute walk to the beach• New pool with in-ground spa• BBQ grill• Outdoor shower• Near Anna Maria Island trolley stopIn the kitchen, you'll find modern stainless steel appliances, sleek granite countertops, and convenient island seating for relaxed dining experiences. Meal prep becomes a pleasure in this fully equipped space. There are two stunning bedrooms, each suitable as a luxurious p

Located in Holmes Beach, Florida, United States. Bluetique: 5 BR, 4.5 BA House in Holmes Beach, Sleeps 10 Bluetique is the perfect place for an extended getaway! The large lot provides plenty of space indoors and out. Bluetique's private pool and spa are surrounded by tropical foliage creating a serene space to take dip or soak in the sun. The covered outdoor dining area by the pool is a great place to enjoy al fresco meals. The home comes equipped with an interior elevator making the property accessible for the entire group. The large fully equipped kitchen opens up to the dining and living rooms with large sliding doors providing access to an oversized outdoor balcony. Take the spiral staircase to the roof top to enjoy incredible views of Bimini Bay, Tampa Bay, and the Gulf of Mexico. Bluetique boasts 4 ensuite bedrooms with king beds and 1 queen bedroom.Please note: Garage is not available for guest use.*Please note: 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with yo

Located in Anna Maria, Florida, United States. 4 FREE BIKES for new fall stays Sep 3-Nov 16 FALL SPECIAL: 4 FREE bikes for reservations *booked after 8/20/24* for stays *arriving between 9/3/24 and 11/16/24*. (Provided by our friends at Beach Bums at 427 Pine Ave, Anna Maria, FL 34216. Guests will need to pick up and drop off bikes.)Looking to escape to a beautiful tropical oasis? This is the place for you! Refreshed with gorgeous coastal decor in the Fall of 2023 and located on the North end of Anna Maria Island, Island Oasis offers 2 bedrooms and 2 baths for your vacation getaway. The master bedroom includes a king bed, private ensuite with walk-in shower, and beautiful French doors that open onto the patio. The adjacent second bedroom includes a queen bed. In the living room you will find a pull-out couch. Take in the sun on the back patio or cool off in the beautiful lagoon-style pool. Make your way up the winding outdoor staircase to take in the beautiful views on the elevated deck. Island Oasis has a private dock to store you

Located in Holmes Beach, Florida, United States. 4 FREE BIKES for new fall stays Sep 3-Nov 16 FALL SPECIAL: 4 FREE bikes for reservations *booked after 8/20/24* for stays *arriving between 9/3/24 and 11/16/24*. (Provided by our friends at Beach Bums at 427 Pine Ave, Anna Maria, FL 34216. Guests will need to pick up and drop off bikes.)Welcome to The Aquamarine, your luxurious retreat for the perfect getaway! This stunning 5-bedroom, 4.5-bathroom vacation home is designed to provide the ultimate blend of comfort, entertainment, and tranquility for up to 10 guests.As you step into The Aquamarine, you'll be greeted by an inviting open floor plan in the main living area, seamlessly connected to a rear balcony overlooking the lush foliage surrounding the heated pool. The pool area boasts a secluded outdoor lounge, perfect for unwinding in the sun or enjoying a refreshing dip in the pool.For those who enjoy a little friendly competition, The Aquamarine offers a two-hole putting green conveniently located next to the pool and lounge area. T

Located in Holmes Beach, Florida, United States. Family friendly, 2 bd, sleeps 6 with wonderful pool. Close to the beach Walk to the beach (5 min walk) or laze by the backyard pool! Or jump on the free island trolley and see the sights.Inquire for monthly rates.Discover the charm of Anna Maria Island from our centrally located Holmes Beach home! This well-appointed 1/2 duplex accommodates up to 6 guests, making it ideal for family vacations, couples' getaways, or trips with friends. The master bedroom boasts a king-sized bed and an en-suite bathroom with a shower, while the second bedroom features a comfortable queen bed. The hall bathroom offers a tub/shower combination. For additional guests, there's a sleeper sofa in the living room.What You'll Love About This Home:Location! 2.5 Blocks to the Beach!2 Bedrooms / 2 Bathrooms1 King/ 1 Queen & Pull Out SofaShared Heated Pool Outdoor ShowerOutdoor Umbrella Patio Seating for 4Pool Loungers & Adirondack ChairsGas BBQ GrillParking for 2 CarsThe fully equipped kitchen includes a coffee ma

Located in Holmes Beach, Florida, United States. Da Beach House: 2 Blocks to Beach, Pool & Spa by Anna Maria Life Vacation Rentals 304 66th St, Holmes Beach, FL 34217What You'll Love About This Home:Location! 2 Blocks to the Beach!2 Bed / 2 Bath2 King Beds, 2 Queen Sofa SleepersPrivate Heated Pool & SpaPool Loungers & Adirondack Chairs2 HammocksPatio Dining Table for 4Screened LanaiGas GrillProfessional Linen Service, Washer & DryerComplimentary WIFIBeach Towels, Beach Chairs, Beach Wagon, CoolersDog Friendly (with fee - see notes below)Parking for 3 CarsDetails:Located a quick walk to the shimmering sand and sparkling clear waters of the beaches of Anna Maria, Da Beach House is a single level vacation retreat. Enjoy the island breezes and relax in paradise.The kitchen, living and dining areas provide space for everyone to relax and enjoy vacation together. The Great Room offers a second gathering room with an additional dining table seating four. Our home is your holiday home away from home.. The master bedroom features a king-size

Located in Holmes Beach, Florida, United States. On Turtle Time - Beautifully Updated w/Heated Pool, Covered Porches, Walk to Beach! Welcome to On Turtle Time!On Anna Maria Island (Holmes Beach, Florida)Beautifully Recently Updated Ground Level Home w/ Private Pool in Holmes Beach, 6-8 min walk to beachHIGHLIGHTS:- Kitchen, Dining, Living w/ Queen Sleeper Sofa & TV- 1 King Bedroom, En-Suite Full Bathroom w/ walk in shower- 2 Twin Bedroom *can be converted into king with advance request- Hall Full Bathroom w/ tub shower combination- Multiple Covered Porches- Heated Pool w/ plenty of sunshineKitchen:Stove/Oven, Dishwasher, Microwave, Refrigerator, Garbage Disposal, Coffeemaker (12 cup), Keurig, Blender, Crock Pot, Toaster, KitchenwarePool Area:Heated Private Pool w/ Table & Chairs, Outdoor Seating & Dining, Grill, Outdoor ShowerLaundry:Washer/DryerParking:1-2 Cars in Driveway/GravelAmenities:A/C, Heat, Cable Television, Wireless Internet, Linens, Towels, Games, Toys, Hair Dryer, Iron/Ironing Board*Beach Gear Equipment (Provided by VayK

Located in Holmes Beach, Florida, United States. Spacious 3 bedroom town home on Anna Maria Island, community pool. For your relaxing and family fun, Anna Maria Island vacation, check out this spacious beautiful 3 bedroom, 2.5 bath town home. Coastal furnished and surrounded by tropical landscape with 2 balconies and a community pool. Enjoy wonderful sunrises and make memories to last a life time!When you arrive at the North Beach Village complex, you'll find this end unit conveniently located just a short walk from gulf beaches and the Holmes Beach town center. Shopping and dining within walking distance, but parking for two vehicles in the garage makes it easy to take the whole family across Anna Maria Island. When you aren't busy exploring Holmes Beach, head over to the heated shared pool for a swim, or lounge on one of the patios with a good book. The ground floor patio is brand new with a cozy fire pit. Inside, this vacation rental offers coastal furnishings and entertainment via the flat screen TV and free WiFi. The fully equip

Located in Holmes Beach, Florida, United States. Luxury home with pool, spa, ping pong, and foosball! Blissful Paradise by AMI LocalsHome in Holmes Beach, FLHighlights:• Heated pool with spa• Foosball and ping pong tables• Chef inspired kitchen with stainless steel appliances • Gas grillHome Layout:Bedroom #1-King BedBedroom #2-King BedBedroom #3-King BedBedroom #4-Twin over Full BunkA beautiful, newly constructed 4 bedroom, 4.5 bathroom home located in Holmes Beach of Anna Maria is the perfect tropical home away from home for your next family beach vacation. An open layout with soaring, vaulted ceilings, coastal furnishings, state of the art stainless steel appliances in your chef inspired kitchen, foosball and ping pong tables, and the large, heated pool w/ spa is just incredible for relaxing after a sun filled day! Only a short walk west and you will arrive to the most pristine, sugary sanded Gulf Beaches. Miles of coastline to discover from sunrise to legendary sunsets and the calm, emerald, green waters are amazing for swimming

Located in Holmes Beach, Florida, United States. Home with Private Pool and Spa. Outdoor TV, Grill - Palms By The Bay Palms By The Bay by Anna Maria Vacations Home in Holmes Beach, FL 34217 VRC16-000361 Welcome to Palms By The Bay! This beautiful home features three bedrooms and three bathrooms, and is located just a short walk away from the stunning Gulf beaches. Spend your days soaking up the sunshine on the sugary white sand, and then retreat back to the backyard oasis for a refreshing dip in the sparkling pool or a relaxing soak in the in-ground spa. Highlights • 10-minute walk to the beach • Private pool with in-ground spa • BBQ grill • Dog friendly • Washer and dryer The living space offers plenty of room to sit back and relax, and enjoy beautiful backyard views. The dining area is the perfect place to gather for meals, and the kitchen is a chef's dream, with stunning granite countertops, custom cabinets, top-of-the-line stainless-steel appliances, and a spacious island with plenty of seating. Each of the three bedrooms plus b

Located in Holmes Beach, Florida, United States. Beach Place... An island treasure. No CAR Needed. You can walk or bike to beach, restaurants, shopping and more. 2 blocks to beach. Perfect area. Need no CAR. Beautifully maintained two-bedroom vacation rental on gorgeous Anna Maria Island. Secluded beaches, shopping, restaurants, golf, fishing and relaxation. Apartment includes full kitchen, 50' flat screen TV in living room, flat screen TV also in one of the two bedrooms, shower & bathtub combination in the bathroom. A private patio area in side yard for outside dinning. Small grill available. Also has an outside shower to rinse off the sand from the beach. There are beach chairs, noodles and umbrellas for your use. WIFI connection included. The apartment has driveway parking. There is easy access to free trolley transportation around the island. The trolley stop is at the corner of this block. This is also one of the golf cart access streets. You will be in a lovely quiet area ideal for walking and biking and only 2 blocks fro

Located in Holmes Beach, Florida, United States. Island Vibe 1: Close to Beach with Private Heated Pool Welcome to Island Vibe 1, a renovated 3-bedroom, 2-bathroom home with private, heated pool and lots of lush tropical landscaping! Located in Holmes Beach, this lovely property is convenient to the beach and in a very quiet Holmes Beach residential neighborhood. It has one shared wall with the unit next door. From here, it's just a short walk to the many shops and restaurants of downtown Holmes Beach, as well as the Island’s only dog park. This beautiful property will sleep 6 people with 1 King bed, 1 Queen bed, and 2 Twin beds. Plus, there is a pullout couch in the living room! You can park up to 3 cars here: 1 in the garage, and 2 in the driveway. In the backyard, you'll find a large open deck and a covered, shaded area overlooking the pool. You can even enjoy drinks at the swim-up tiki table in the pool! We've added solar string lights on the upper and lower patio for enjoying the outdoors during those great Florida evenings.You'

Located in Holmes Beach, Florida, United States. Perfect family vacation home with pool, lounge, and ping pong! Coconut Cottage by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217VRC16-000159Welcome to Coconut Cottage, a beautiful vacation rental with a sparkling pool that is just a quick walk to the stunning turquoise Gulf waters of Holmes Beach! This three bedroom and two and half bath dream home is packed with amenities including a PlayStation 4, Ping Pong Table, and has a stunning backyard perfect for making lifetime memories with friends and families.Highlights• Less than a 5-minute walk from the beach • Private pool • Game room with PlayStation 4 and Ping Pong• Veranda This coastal home has an inviting living room, a fully equipped kitchen with stainless steel appliances, a dining room, and a stunning veranda. The primary bedroom offers the ultimate relaxation spot with access to the veranda, where you'll find plush seating and a beautiful tropical setting with sparkling pool views. The spa-like ensuite bathroo

Located in Holmes Beach, Florida, United States. Turtle's Bay managed by Beach Retreats 306 Clark drive (B) Holmes Beach, FL 34217VRC17-000009Dog Friendly! Beautiful open concept home. 3 king bedrooms with en suites and a den with 2 single bunk beds make this property perfect for multi-generational or multi-family vacations. This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relaxing by the heated pool in your own backyard oasis. This house has every luxury you could want, Flat-screen TV's, stainless steel appliances, beautiful 'wood' tile floors, quartz countertops, free phone/cable/wireless Internet Take the free trolley to Bean Point, or historic Bridge St. Have a bite at Chateau Anna Maria, or the Beach Bistro or grab a burger and enjoy the game at Skinny's. Go paddle boarding or kayaking in the crystal clear blue waters in the Gulf Of Mexico.​​​​​​​We might be only 7 miles long but Anna Maria has everything you could possibly need for your perfectb

Located in Anna Maria, Florida, United States. Home with Pool and Spa, tropical backyard! Near the beach - Feelin' Beachy Feelin’ Beachy by AMI LocalsHome in Holmes Beach, FloridaVRC20-000140Let the good times roll at Feelin' Beachy, a stunning four-bedroom and four-and-a-half-bathroom home with a luxurious backyard featuring a sparkling pool, an in-ground spa, and there are two covered patio areas with plenty of outdoor seating! Highlights• Private Pool and In-ground Spa• Less than a 5-minute walk to the beach• Near Anna Maria Island Trolley Stop• Foosball Table• Dog Friendly No detail was missed when designing Feelin' Beachy; there is natural light from the large windows throughout the home. The kitchen has stunning backsplash, stainless steel appliances, a wine fridge, and island seating. There is a comfy seating area and a formal dining room with a modern table. Through the sliding glass doors in the poolside deck with a complete dining set. Follow the stairs to the third floor to the spectacular primary bedroom featuring an

Located in Anna Maria, Florida, United States. Salty Pirate - Luxury Canal Front Home w/Water View, Pool/Spa, Bikes, Kayaks, Toys! Welcome to Salty Pirate!On Anna Maria Island (Anna Maria, FL)2512 sq. ft.Need more room? Reserve the sister 4 bedroom home next door, Seaswept Mermaid (#1850215), to stay at The Pirate and His Mermaid homes for a total of 8 bedrooms!HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV, Plenty of Outdoor Deck spaces- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower, Double Vanity, & Soaking Tub- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower- 1 Queen Bedroom w/ TV, En-Suite Full Bathroom w/ Shower- 1 Triple Bunk Room & Queen Bedroom w/ TV & Xbox- Bonus Game Room off Pool/Patio Area & Backyard w/Ping Pong Table, Games, Bikes, Extra Fridge, Kayak, SUP BoardKitchen:Stove, Oven, Dishwasher, Microwave, Refrigerator w/ Ice Maker & Water, Garbage Disposal, Coffeemaker (12 cup), Blender, Crock Pot, Toaster, Kitchenware, Wine Cooler, KeurigPool Area:Heated Private Pool w/ Spa, Table &

Located in Holmes Beach, Florida, United States. Close to Beach with Private Saltwater Pool - Casa Azul Casa Azul by Anna Maria Island LocalsHome in Holmes Beach, FLVRC21-000108 Casa Azul is a stunning vacation home nestled in the heart of Anna Maria Island, offering three beautiful bedrooms and three bathrooms for the ultimate beach getaway. The lush tropical landscaping surrounding the saltwater pool creates a serene oasis, complete with lounge chairs, outdoor dining, and a BBQ grill for alfresco meals. Highlights • Less than a 10-minute walk to the beach • Saltwater pool • BBQ grill • Balconies • Near restaurants Inside, coastal vibes blend seamlessly with high-end furnishings, creating a relaxing ambiance throughout. The well-appointed kitchen, coffee bar, and dining area provide everything needed for hosting family gatherings. The primary bedroom offers a tranquil retreat with its secluded balcony and ensuite bathroom with a walk-in shower, while the second bedroom boasts luxury amenities and a private ensuite. The third bedroo

Located in Holmes Beach, Florida, United States. Charming Private Home, Private Pool and Spa. Fenced Yard, Updates Throughout Seahorse Cottage by AMI LocalsHome in Holmes, Beach FloridaVRC16-000110Enjoy a luxury vacation with friends and family at Seahorse Cottage, a three-bedroom and three-and-a-half-bath home. This getaway is just a quick walk to the pristine Gulf of Mexico beaches and is across the street from the free trolley stop. Take advantage of the wonderful amenities, including a private pool, hot tub, and an excellent patio with a built-in grill. Highlights• Less than a 10-minute walk to the beach• Private pool and hot tub• Anna Maria Island Trolley stop across the street• Covered patio with built-in grillEnter through the front door and be welcomed into a beautifully decorated coastal living area with two blue couches, wicker chairs, and a TV. The kitchen has basic culinary essentials, louvered cabinet doors, stainless steel appliances, countertops with breakfast bar seating, and a beachy dining room table. On the main

Located in Holmes Beach, Florida, United States. 1 Block to Beach on Private Lake Heated Pool, SPA 6937 Holmes Blvd. WE ONLY RENT FROM SATURDAY TO SATURDAY WITH A 7 NIGHT MINIMUM!!6937 Holmes Blvd, Holmes Beach, FL 34217. Google us for maps for relative location to beach and Gulf.We installed a new pool with a spa in 2016. This island home just one block from the beach offers a one of a kind setting which affordably gives you the pleasures of a spring-fed lake with dock as well as one block (3 minute walk) to the beach with a peek of the gulf. The beautiful lake is home to all types of fish ranging from Snapper, Redfish, Tarpon and Mullet. Practice your fishing skills. (Please keep in mind for all of our future enjoyment we do practice catch and release.) You will enjoy the very light and open floor plan immaculately furnished with three bedrooms and two full baths as well as an outside shower. The third bedroom includes a handsome writing desk and TV. Enjoy your morning coffee and sunrise on the beautiful awning covered back b

Located in Anna Maria, Florida, United States. Canal front home with a pool and boat dock! Highlights• Canalfront with dock• 5-minute walk to the beach • Private pool• Putting green • Pool Table and Ping Pong TableShore Bet by AMI Locals 220 Periwinkle PlzAnna MariaVR21-000037Welcome to Shore Bet, a spectacular canalfront vacation home with a private pool and dock just five minutes from the beach! This rental has three bedrooms and three bathrooms. The open modern living area has large windows that let in the bright Florida sun and gives guests a relaxing place to connect with friends and family or have a movie night. Additionally, the living space opens up to the screen-in patio with stunning views of the canal for guests to enjoy while relaxing and discussing Anna Maria Island activities. The fully equipped kitchen has plenty of space for making homemade island-inspired meals and snacks for the beach. Guests can enjoy a quick bite to eat at the kitchen island and enjoy homemade meals and the best Anna Maria Island take-out at the

Located in Holmes Beach, Florida, United States. Coco Cay - Beautiful totally remodeled 4 bedroom with private pool This beautiful, newly remodeled home is the perfect island getaway for your family vacation or group of friends with 4 bedrooms and 4 baths our Coco Cay can easily accommodate 9 people. The home provides a spacious open living area. You will notice the stainless-steel appliances, teal accents, and coastal décor as soon as you step into this island gem. Coco Cay also has a large flat screen TV, state of the art LED bathroom mirror, and whimsical artwork throughout. The game room conveniently adjacent to the kitchen with a pool table and dartboard will provide hours of entertainment for everyone of all ages. There also is a screened in patio off the living room for a quiet moment or a chance to catch up on a good book. The back yard provides a privacy fence to ensure lounging by the pool or barbeque time in a tranquil setting or in the evening you may choose to sit by the fire pit. Remember you are a short stroll down th

Located in Holmes Beach, Florida, United States. Seaside Sunset- Waterfront 2 master suites, bunkbed room, and private boat dock Waterfront home with private dock and boat slip, centrally located in beautiful Holmes Beach! Just a half mile from the beach (3.5 blocks) and walking distance to the city park with playground, tennis and pickleball courts, and boat ramp. Many highly rated restaurants, bars, and shops to choose from! Covered patio with sunset views overlooking the water where manatees and dolphins frequent. Fish cleaning station and outdoor shower make this a fisherman's paradise!