58,368 properties available

Located in Captiva, Florida, United States. 2 Spacious Villas, Free Parking, Beach and Pool The ultimate vacation spot! Enjoy access to the abundance of resort amenities on this property: from great pools and tennis courts to poolside chairs and towels provided at no extra charge! This property, which boasts a genuine old Florida feel, is surrounded by a 330-acre wildlife preserve, where dolphins and manatees are regular guests. Here you’ll find everything you need to live that dreamy island life. Fill your days with kayaking, sailing, boating, bicycling, golf, and tennis. Enjoy epic fishing, world-famous shelling, or just strolling along the spectacular 2.5-mile stretch of private pristine beach. ATTENTION: PLEASE BE ADVISED THAT A MANDATORY RESORT FEE of $25 PER EACH PERSON OVER 13 YEARS OLD PER NIGHT PLUS TAX WILL BE CHARGED UPON ARRIVAL. ALSO, A MANDATORY SERVICE CHARGE OF 12% OF THE NIGHTLY RATE, PLUS TAX, WILL BE COLLECTED UPON ARRIVAL. The listing is distributed and managed by RoomPicks AccommodationsPLEASE NOTE: These a

Located in Captiva, Florida, United States. 3 Bedroom Villa on South Seas Resort, Captiva Island, Florida Feel right at home overlooking the bay in this 2 floor villa. Eat breakfast watching dolphins and manatees on your private lanai overlooking the bay.Large Kitchen, great room, large dining area (seats 8 easily), and half bath on top level. Large screened porch on top level also has dining furniture. First floor includes master bedroom with walk in closet and large full bath, second bedroom with 2 twin beds, large closet, and attached full bath with shower/tub, and third bedroom with double bed and closet. All bedrooms have TV's. Your own washer/dryer also on entrance level. Also large covered garage on ground level below unit. Walk down steps from master bedroom to private area with hot tub (shared by 4 units only) and grill (only shared with one other unit).Kayak from your back yard into bay. Walk across narrow road to pool and beach of Gulf of Mexico. Beach is never crowded (even at spring break!) b/c is only for resort

Located in Captiva, Florida, United States. Get Ready for Adventures! 2 Elegant Villa Units, Pools, Beach Access, Restaurant The ultimate vacation spot! Enjoy access to the abundance of resort amenities on this property: from great pools and tennis courts to poolside chairs and towels provided at no extra charge! This property, which boasts a genuine old Florida feel, is surrounded by a 330-acre wildlife preserve, where dolphins and manatees are regular guests. Here you’ll find everything you need to live that dreamy island life. Fill your days with kayaking, sailing, boating, bicycling, golf, and tennis. Enjoy epic fishing, world-famous shelling, or just strolling along the spectacular 2.5-mile stretch of private pristine beach. ATTENTION: PLEASE BE ADVISED THAT A MANDATORY RESORT FEE of $25 PER EACH PERSON OVER 13 YEARS OLD PER NIGHT PLUS TAX WILL BE CHARGED UPON ARRIVAL. ALSO, A MANDATORY SERVICE CHARGE OF 12% OF THE NIGHTLY RATE, PLUS TAX, WILL BE COLLECTED UPON ARRIVAL. The listing is distributed and managed by RoomPicks A

Located in Captiva, Florida, United States. Captiva Cottage #3 Bayfront 1 Bedroom / 1 Bath Cottage "New and Beautiful coming soon !! Currently under construction for a fresh and stunning new look" Captiva Cottages are eight vacation cottages on landscaped grounds, right on the water facing Pine Island Sound. Relax among peaceful, natural beauty and enjoy the shared pool. The cottages are ground-level for easy access, and the shops, restaurants, and activities of the Captiva Village are about one minute’s walk. These cottages are undoubtedly the best value on Captiva Island, offering an outstanding waterfront location and clean, comfortable interiors at a bargain price. They are perfect for extended-stay couples, naturalists, and larger families and groups (rent several cottages).Smart TVs ( 50 inches or larger) are located in both the living room and bedroom of the cottage!Captiva Cottages provides beach towels, beach chairs, and a beach umbrella for your day at the beach! Parking is limited to one car. The dock is now available

Located in Captiva, Florida, United States. Your Home Away From Home! 2 Family-friendly Villas, Access to Tennis Court! The ultimate vacation spot! Enjoy access to the abundance of resort amenities on this property: from great pools and tennis courts to poolside chairs and towels provided at no extra charge! This property, which boasts a genuine old Florida feel, is surrounded by a 330-acre wildlife preserve, where dolphins and manatees are regular guests. Here you’ll find everything you need to live that dreamy island life. Fill your days with kayaking, sailing, boating, bicycling, golf, and tennis. Enjoy epic fishing, world-famous shelling, or just strolling along the spectacular 2.5-mile stretch of private pristine beach. ATTENTION: PLEASE BE ADVISED THAT A MANDATORY RESORT FEE of $25 PER EACH PERSON OVER 13 YEARS OLD PER NIGHT PLUS TAX WILL BE CHARGED UPON ARRIVAL. ALSO, A MANDATORY SERVICE CHARGE OF 12% OF THE NIGHTLY RATE, PLUS TAX, WILL BE COLLECTED UPON ARRIVAL. The listing is distributed and managed by RoomPicks Accomm

Located in Captiva, Florida, United States. Captiva Cottage #2 Bayfront 1 Bedroom / 1 Bath Cottage "New and Beautiful coming soon !! Currently under construction for a fresh and stunning new look" Captiva Cottages are eight vacation cottages on landscaped grounds, right on the water facing Pine Island Sound. Relax among peaceful, natural beauty and enjoy the shared pool. The cottages are ground-level for easy access, and the shops, restaurants, and activities of the Captiva Village are about one minute’s walk. These cottages are undoubtedly the best value on Captiva Island, offering an outstanding waterfront location and clean, comfortable interiors at a bargain price. They are perfect for extended-stay couples, naturalists, and larger families and groups (rent several cottages).Smart TVs ( 50 inches or larger) are located in both the living room and bedroom of the cottage!Captiva Cottages provides beach towels, beach chairs, and a beach umbrella for your day at the beach! Parking is limited to one car. The dock is now available

Located in Captiva, Florida, United States. Captiva Cottage # 8 Bayfront 1 Bedroom / 1 Bath Cottage "New and Beautiful coming soon !! Currently under construction for a fresh and stunning new look" Captiva Cottages are eight vacation cottages on landscaped grounds, right on the water facing Pine Island Sound. Relax among peaceful, natural beauty and enjoy the shared pool. The cottages are ground-level for easy access, and the shops, restaurants, and activities of the Captiva Village are about one minute’s walk. These cottages are undoubtedly the best value on Captiva Island, offering an outstanding waterfront location and clean, comfortable interiors at a bargain price. They are perfect for extended-stay couples, naturalists, and larger families and groups (rent several cottages).Captiva Cottage #8 is special in that it has a bright full-width porch facing the pool and the bay. Wake up to great sunrise views from your kitchen or porch, or take your coffee and enjoy the wildlife (fish, marine mammals, and abundant birds).Smart TV

Located in Anna Maria, Florida, United States. Great Beach Retreat w/Full Kitchen, Free WiFi, Shared Pool, Washer/Dryer, & More Sunrise Garden #9Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located on the bottom floor, these poolside suites are ideal for a refreshing and rejuvenating beach escapade. They are well-appointed to meet every guest's expectations no matter what! Featuring a fully-equipped kitchen with all the needed appliances and cooking essentials (no dishwasher), access to a shared swimming pool and a laundry facility, and free WiFi, a relaxing beach-cation awaits here! The front door leads out into your own patio area surrounded by lush landscaping.Let the charming hidden gem that is Anna Maria melt your stress away with its postcard-perfect beaches, easy access to deep-sea fishing and ocean adventures, and tranquility that you can only find in a small town. Restaurants surround you every way you go, so feel free to take a brea

Located in Anna Maria, Florida, United States. Serenity Cove: North End Cottage on Canal, Kayaks, Perfect for 2 by Anna Maria Life Vacation Rentals Serenity Cove by Anna Maria Life Vacation Rentals606 N. Shore Drive, #5, Anna Maria, FL 34216What You'll Love About This Home:Location! North End AMI Canal Home! Steps to the Gulf Beaches!1 Bedroom / 1 BathroomQueen BedBackyard Dock (shared with other 2 cottages)Kayaks - 3 Single & 2 Double (shared with other 2 cottages)'HammockGas BBQ GrillProfessional Linen Service, Washer & DryerComplimentary WIFIDog Friendly (with pet fee - see below)Beach Towels, Beach Chairs, Beach WagonParking for One CarDetails:Located on the coveted North End of AMI, our one-bedroom cottage is the quiet getaway you are looking for. Enjoy the tranquil north end of the while remaining within walking distance of the beach, shops, and restaurants.The living room in Serenity Cove captures the essence of comfort through the inclusion of two oversized recliners settled in front of a large flat-screen television. The s

Located in Anna Maria, Florida, United States. BEST LOCATION! NORTH END OF ANNA MARIA, FL STEPS TO BEACH & DINING - UPPER UNIT Location!!! North end of Anna Maria Island . Steps to the Bean Point Beach and everything you need for your perfect Anna Maria Vacation. The Blue Dolphin Inn consists of four units surrounding a free style heated pool. Rent one unit or all. Perfect for a group of extended family and friends who want their own place but still be right together as a group. Heated inground pool, steps to the Bean Point Beach. Parking is right at the front of the property and is limited to two cars. The unit features a private patio area and outdoor shower. Gas grill available by the poo area. This unit has a queen, 2 twin beds. Wifi internet, TV's in all rooms. Low traffic area makes it safe to use the bicycles to get around. Easily travel across the island on the free trolley, which runs every 20 mins and has many stops around the island. There are many places who offer bikes and golf carts for rent in the island . There ar

Located in Anna Maria, Florida, United States. Sea Song - DIRECT GULFRONT HOUSE - By Island Real Estate Vacations “Sea Song” is an adorable Anna Maria Island vacation rental cottage nestled in the flour soft sand of Bean Point to allow you to smell the salt air! Accommodating up to 6 guests, this 2 bedroom 1 bathroom home offers 2 king beds and a queen sleeper sofa.This "Old Florida" beach front cottage has been fully renovated, and is tucked away in a quiet neighborhood of the city of Anna Maria within in walking distance of fabulous Pine Avenue shopping, dining, sightseeing, and free trolley stops. During your stay near Pine Avenue be sure to enjoy sights like the Anna Maria city pier and the historic jail house. Dine on Pine Avenue any meal of the day with The Donut Experiment, Poppo’s Taqueria or The Waterfront.Anna Maria vacation rental “Sea Song” is well appointed with everything you need for a gorgeous relaxing vacation. The spacious bedrooms are decorated in cool tropical pastel colors, and the bathroom offers a tub shower

Located in Anna Maria, Florida, United States. Charming Canal front Luxury home with brand-new Pool! Dockside Paradise by AMI LocalsHome in Anna Maria, FLFeatures:• Canal front home• private pool• close to Pine Avenue for shopping and dining• Just a 4-minute walk to the Bay side beach and an easy 10-minute walk to the Gulf beachRoom Details -Primary Bedroom: King bed, shares hallway bathroom with shower/tub combination-Second Bedroom: King bed, ensuite bathroom with walk-in shower and outdoor pool access door-Sunroom off the kitchen: Twin Day Bed with Trundle-Queen sleeper sofa Dockside Paradise is a perfect canal front retreat centrally located in Anna Maria! Completely updated and fully outfitted, Dockside Paradise is decorated in a fun beachy style! The new pool was just added to this beautiful home's private backyard space and you will spend a lot of your vacation out here, enjoying the Florida sunshine and just relaxing. The home and dock are perfect for fishing. Dockside Paradise has everything you need for an amazing Anna M

Located in Anna Maria, Florida, United States. 4 Bed / 4 Bath with Stunning Views of Bimini Bay ! You will love Bimini Bay Vue, its breathtaking, unobstructed 180-degree angle views of Bimini Bay are stunning. Completely renovated in 2022 this 4 bedroom and 4 bathroom ground view home is the ideal location for you to enjoy your family vacation. Complete with a large open-concept common area off of the kitchen which allows for dining and spacious living. One has the option of eating inside or outside under the pergola with a full view of Bimini Bay. Choose to relax by the saltwater pool, fish on the dock, watch the birds and fish, practice putting on the green, watch the boats go by, and lose yourself in our spectacular sunsets. There are shaded and sun-soaked areas. Each of the 4 bedrooms has its flat screen tv and bathroom. There are 3 king bedrooms and a bunk room complete with 2 single over double bunk beds. The home sleeps up to 8 people. Bimini Bay Vue home is tucked away in a quiet neighborhood at the end of Tarpon St., just

Located in Anna Maria, Florida, United States. Zen Gardens in Anna Maria *3 Night Minimum stays are allowed during low season, please refer to the rate table for the specific date ranges* Welcome to Zen Gardens on beautiful AMI. BIG NEWS: a brand new, full sized pool and spa was installed and is ready for your use. Zen Gardens is located just north of Pine Ave - and 1 house from the beach - in the City of Anna Maria. This property offers a beachy bohemian vibe and has all you need for a memorable stay on Anna Maria Island. This ground level cottage has been professionally decorated and updated for your enjoyment. Leave your car parked - the City of Anna Maria is very walkable. Zen Gardens is Located only a few flip flop steps away from the gorgeous white sand gulf beaches and the many shops and restaurants on Pine Avenue. If you want to explore Anna Maria Island, our Islands free trolley service is close by! This charming Zen cottage offers 3 Bedrooms and 2 Bathrooms. The master suite f

Located in Anna Maria, Florida, United States. Experience Family Fun at Blue Pearl: Steps from Beaches, Shops, and Dining! Blue Pearl By AMI LocalsHome in Anna Maria VR19-000007Discover paradise at Blue Pearl! This beautiful three-bedroom, three-bath home with a private suite is perfect for family gatherings. Located near famous Pine Avenue, enjoy easy access to shops, restaurants, and attractions like Rod N Reel Pier and AMI City Pier. Plus, you’re just a short walk from pristine Gulf beaches, ideal for soaking up the sun and taking in coastal views! Highlights • 7-minute walk to the Beach • 3-minutes to Dining and Shopping • Private Pool with In-Ground Spa • Separate Private Suite • Outdoor Dining and Grill • Washer and Dryer • Dog friendly with approval and additional fee Your Backyard Oasis Awaits! Indulge in sunny afternoons in your private backyard retreat, featuring a sparkling pool and spa surrounded by lush greenery. Unwind on comfortable outdoor seating, fire up the BBQ grill for delicious cookouts, and gather around the

Located in Anna Maria, Florida, United States. Luxury Home with Pool, Spa, Rooftop, a block from the Beach - Paradise Bound Paradise Bound by AMI LocalsHome in Anna Maria, FloridaVR21-000036Welcome to Paradise Bound, a four bedroom and four bathroom retreat with a rooftop deck that boasts Gulf views (which is just three houses away!) and a private backyard with a sparkling pool, spa, and outdoor BBQ space. Highlights • 2-minute walk to the beach• Private pool with in-ground spa• Rooftop deck• BBQ grill• Near restaurants and shopsInside is an open floor plan with chic seating area, a smart TV, and a wet bar with a wine fridge. The kitchen is a dream with stainless steel appliances, ample cabinet space, a spacious center island complete with barstools, and easy access to the formal dining table.Take the private elevator to the third floor, where you will find the primary bedroom. This serene space is decorated with beautiful nautical touches, and you will enjoy a premium mattress, balcony access, and a private ensuite bathroom with a

Located in Anna Maria, Florida, United States. Bean Point Residence Unit A by SeaBreeze Vacation Approximately 40 steps and you'll be at the beach entrance to Anna Maria's sandy, white beach. This property offers convenient access to one of the island's main attractions. As the upper level of a two-unit home, Bean Point Residence Unit A boasts 3 bedrooms/3 bathrooms, providing ample space for families or groups of friends. The huge kitchen with granite countertops and stainless steel appliances is perfect for gatherings, with an open-concept design that flows into the dining area and family room, making it ideal for socializing and relaxing. Enjoy stunning sunset views from the balcony, offering a picturesque setting for evenings spent outdoors. The large primary bedroom features a king-size bed and a sleeper sofa, along with its own private bathroom for added comfort and convenience. Bedroom 2 offers a king-size bed while Bedroom 3 features a queen-size bed, with both rooms sharing a hallway bathroom. Washer and dryer are in a ha

Located in Anna Maria, Florida, United States. Stunning 3Bed/3 Bath, Heated Pool, FREE WiFi, Close to Beach, On Canal to... **ASK ABOUT LAST MINUTE DEALS! Welcome to paradise at Pelican Point! This stunning 3 bedroom/3 bath home has everything you need to enjoy a wonderful vacation on beautiful Anna Maria Island. Located right on a canal, you can enjoy the amazing views of the water and pool from your screened-in porch off the living room area. The inviting pool has plenty of space to relax and enjoy the spectacular Florida weather including plenty of seating, a poolside "beach" with sand, a TV, a fire pit and a shaded area to relax and enjoy. Right on the canal is a dock where you can fish or launch your kayaks. It is located close to open waters and the beaches of Anna Maria are only a few blocks away. Bringing a Boat? There are 2 humpback bridges to cross under with 6' to 7' height restrictions at low tide. Launch at Holmes Beach Boat ramp at 6398 Marina Way, Holmes Beach, FL 34217. Contact the office f

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.)Beautiful waterfront home located on the north end of Anna Maria Island. Located on North Shore Drive, approx 9 houses east of the Rod n Reel Pier and half a mile from the Historical City Pier. Anna Maria Island is a piece of old Florida. Perfect for family vacations, swimming, and watching the dolphins. 100 ft of private beach is all yours! Relax on the large back deck as you watch the waves and dolphins.This waterfront property is an ideal location that is walking distance to restaurants, the Gulf beaches quaint ice cream shops and so much more. You can rent bikes, golf carts, and other essential island equipment nearby on Pine Ave.Nice easy beach, perfect for little children. We enjoy the pine tree i

Located in Anna Maria, Florida, United States. Point's Hideaway - Beautiful Home w/Stunning Sunset/Water Views on Bean Point! Pool, Bar, Foosball! Welcome to Point's Hideaway!On Anna Maria Island (Anna Maria, FL)HIGHLIGHTS:- Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/Walk in Shower- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/Shower Tub Combo- 1 King Bedroom w/TV- Sleeper sofa (sleeps 2)- Full Bath w/Walk in Shower- Game Room w/ Wet Bar, Foosball Table, Beverage Cooler and TV- Multiple Outdoor Spaces! Screened-in porch & HUGE Rooftop Deck!- PET FRIENDLY!Kitchen:Gas Range, Oven, Dishwasher, Microwave, Refrigerator, Garbage Disposal, Coffeemaker, Blender, Crock Pot, Toaster, Kitchenware, Wine CoolerPool Area:Heated Private Pool w/ Table & Chairs, Outdoor Seating, Loungers, Gas Grill, Outdoor ShowerApproximate Pool Size:24' x 9'Laundry:Washer/DryerParking:1-2 Car Garage Cars in Garage & 1-2 Cars in DrivewayAMENITIES:A/C, Heat, Cable Television, Wireless Internet, Linens, Towels, TVs, Foosball, Toy

Located in Holmes Beach, Florida, United States. 180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow Bay Vista at Bayside Bungalow by AMI Locals Home in Bradenton Beach, FL 34217 VR18-000088 Welcome to Bay Vista, a luxurious second-floor condo with three bedrooms and two bathrooms! This unit features 180-degree wrap-around windows, where you can watch sailboats, Florida marine life, and stunning sunrises right from the comfort of your living room. Plus, the condo offers a range of shared amenities that will further elevate your vacation experience! Highlights• Shared pool• Less than a 15-minute walk to Gulf beach• Across the street from Bay beach• Shared BBQ area• Near restaurants and boutiques There are plenty of comfortable seating options for guests to socialize or unwind in the spacious living area that perfectly captures the essence of coastal living. The fully equipped kitchen has stainless steel appliances, including an electric range and dishwasher, and an island bar. The main bedroom is a cozy an

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.)Welcome to Aloha Beaches a newly renovated custom beach destination. Kick off your shoes, turn off your phone, don’t wind your watch, leave sweaters unpacked and wear your bathing suits from breakfast to bedtime. Are we there yet? Palm trees, blue skies, balmy temperatures, a porch swing, the beach and the sun. All are included at the secluded and stylish beach hideaway: Aloha Beaches. Nestled on a north end street and only a short stroll to the sugar white beaches of Tampa Bay and Pine Ave, Aloha Beaches is comfortable and airy, decorated for relaxed vacation living and spirited entertaining.***OVERCROWDING CONSEQUENCES***Maximum occupancy of rental homes on Anna Maria Island are set by the Cities and

Located in Anna Maria, Florida, United States. Charming cottage with heated pool, tropical landscaping in prime location. The Starfish Cottage has been recently renovated while maintaining all the charm of an old Florida Key West style bungalow. Enjoy the new private heated pool with lush tropical setting. The new kitchen provides plenty of storage , a full sized refrigerator and freezer, dishwasher, range and microwave. There's also an outdoor grill. The large screened in porch features a vaulted ceiling, large ceiling fans, plenty of seating including rocking chair and swing bench. On the porch a dining table accommodates 8 and a small bistro table seats 2. Inside you'll find an open concept living space where dining area, kitchen and living room have been newly furnished with luxurious deep seat couches and lounge chairs, original hardwood floors add to the charm. Fresh linens, bath and beach towels are provided along with basic toiletries. Decor has been collected over time and obtained from local artists for a unique old Flori

Located in Anna Maria, Florida, United States. Pier Pleasure - Anna Maria at it's finest! Pool, hot tub, beach, putting green Luxury abounds in this lovely home on the north end of Anna Maria. Every inch of this home was built in a well thought out manor with elegance and comfort in mind. This magnificent and sprawling estate has four bedrooms, 4.5 bathrooms and a bonus room children to congregate and play games. The bonus room is equipped with full beds and bunks. All other bedrooms have King size beds. The home is three stories with an elevator that goes to all floors, except for the roof top deck. The ground level will grab your attention with the spacious under roof, open air gathering area. This area has plenty of comfortable seating by the gas fireplace, an eight seat dining table, large flat screen TV, putting green and completed with an amazing pool and hot tub. Moving to the second floor, you will immediately be enchanted by the gorgeous views of the Tampa Bay and Sunshine Skyway. The spacious