Resort holiday rentals in Anna Maria Island

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Top-rated resort stays in Anna Maria Island

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Guest favourite

Private room in Ruskin

4.83 out of 5 average rating, 36 reviews

Little Harbor Hideaway

Welcome to Little Harbor Hideaway! Enjoy the Beach, 2 pools,Hot Tub & Kayaking on Cabbage Creek. We also have 2 restaurants on property. * New PickleBall courts & CornHole boards Our Unit has a very nice king bed as well as a sectional couch with pull out full bed. This unit has a full refrigerator and also has a built in flat top electric stove. 50in Sony Smart TV for Netflix etc +cable New A/C in late 2023 This is a 2nd FL unit w/ large Balcony new Washer & Dryer in common area near steps.

Guest favourite

Private room in Dunedin

4.95 out of 5 average rating, 44 reviews

Best of Beso ADA Deluxe 1BR/2BA Water View Suite

Stay in the heart of it all at this one-of-a-kind, unique double unit condo boasting a view, with 2 balconies, 2 bathrooms and a private bedroom suite. This upscale, tropical oasis is located right off the Gulf of Mexico’s St. Joseph Sound! ENJOY Beso Del Sol Resort’s Waterfront Pool Deck & Marker 8 Tiki Bar, Spectacular Sunsets, Docks, Complimentary Fishing Poles & Bikes. Boat Slips are also available. A Beautiful Venue, perfect for any occasion, is conveniently located on property for rent.

Superhost

Private room in Indian Rocks Beach

4.81 out of 5 average rating, 26 reviews

Two Bedroom Suite With Waterpark Passes

Beautifully renovated unit located in the Marker 33 Harbourside Condos. On the property is the well known Splash Harbour Waterpark. You have full access to the resort that offers 18 hole mini golf($7.95), swimming pool, hot tub, 3 bars and full service restaurant. It is close to the beach, family-friendly activities, and nightlife. You’ll love my place because of the views and the location. My place is good for couples, solo adventurers, business travelers, families (with kids), and big groups.

Guest favourite

Private room in Anna Maria

4.99 out of 5 average rating, 68 reviews

Blue Dolphin AMI Jacaranda Lower 2b/1b

Location!!! North end of Anna Maria Island . Steps to the Bean Point Beach and everything you need for your perfect AMI 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. The Ibis unit features a private patio area with a gas grill specific to this unit. Unit has a queen, 2 twin beds. Parking is limited to two cars. MAX Occupancy - 4 people including children of any age.

Superhost

Private room in Sarasota

4.68 out of 5 average rating, 22 reviews

Condo Retreat Near IMG Academy & White Beach sand

Discover serenity in Sarasota Waterfront, your ideal escape. Situated with great convenience, just off US-41, we're perfectly located near downtown Sarasota and Sarasota Bradenton International Airport. Our prime location brings you within arm's reach of the stunning white sand beaches and clear waters of Siesta Key, Lido Key and Anna Maria Island. Our accommodations feature captivating views of Sarasota Bay's tranquil waterfront, where breathtaking sunsets and marina scenes!!

Guest favourite

Private room in Nokomis

4.76 out of 5 average rating, 17 reviews

Waterfront One Room Bungalow with Private Beach -7

Just 15 feet from the Venice Inlet, this waterfront studio has just been remodeled with queen tempurpedic bed, waterfront patio, and roll-in showers with rain shower head. Enjoy a kitchenette and french doors facing the Water on this Beach to Bay property. The private Gulf beach of Casey Key is just 200 feet from your door. Casey Key Resort provides a unique experience on Casey Key -- With Gulf Front beach on one side of the property and Venice Inlet waterfront on the other!

Guest favourite

Private room in Ruskin

4.85 out of 5 average rating, 192 reviews

Sunset on the beach

See the sunset from your balcony overlooking Tampa Bay and the St. Petersburg skyline in this cozy room that sleeps 3. Enjoy two heated swimming pools, a hot tub, fitness center and tennis and pickleball courts. There is also a small game room available. There is a small children's playground and outdoor basketball court as well as cornhole and shuffleboard areas. The unit is exactly like a hotel room complete with full size refrigerator, Keurig, microwave and toaster.

Guest favourite

Private room in Holmes Beach

4.93 out of 5 average rating, 29 reviews

The Lady/Studio 21

Palm Tree Villas offers a portfolio of eight unique 1950's resort rooms ranging from small studios to three bedroom villas with three bathrooms. We would love to host you for a wonderful quaint island getaway vacation. Conveniently close to the trolley line for a quick bite at many great eating spots around the island and close enough to walk to the beach in a few minutes. Park your car and enjoy the island. This offering is an extremely private popular studio.

Private room in Indian Rocks Beach

4.71 out of 5 average rating, 38 reviews

Waterfront Two Bedroom Suite With Waterpark Passes

Located directly on the Intracoastal Waterway we are a short walk to the beach. Take a dip in our heated garden pool and hot tub. Enjoy the all new Splash Harbour Water Park. There is also an onsite 50 slip marina with boat rentals and fishing charters, an 18-hole miniature golf course, game room, fitness center & gift shop. We are ideal for couples, solo adventurers, business travelers, families and large groups.

Guest favourite

Private room in Treasure Island

4.95 out of 5 average rating, 42 reviews

Treasure Island Beachfront Resort with pool

Amazing beach views from your vacation condo unit and from your private balcony. Newly refreshed privately owned condo at the Island Inn Beach Resort in Treasure Island Florida. Treasure Island is next to St. Pete Beach, south of John's Pass, Madeira Beach, Indian Rocks and Clearwater beaches. Pool bar, heated pool on beach, kitchen with two burner hot plate, pots, pans, coffee maker, microwave and more.

Guest favourite

Private room in Siesta Key

4.97 out of 5 average rating, 36 reviews

The Nook, with heated pool.

The Inn is conveniently located on Siesta Key directly across the street from the Beach. Its guests enjoy beach access right across the road ( access #9 ). Siesta Village is also just a 5-minute walk from the Inn. If walking is not an option there is a trolley that is free of charge to ride and get around the Key. We have 6 Cottages in total that range from a one bedroom units to a two bedroom units.

Superhost

Hotel room in Nokomis

4.84 out of 5 average rating, 64 reviews

Ocean Front Apartment

We are a family friendly resort located directly on the Gulf of Mexico and the Inter-coastal Waterway on picturesque Casey Key Florida. Our well equipped guest rooms are available for daily and weekly rentals. Here you can enjoy a serene and quiet tropical paradise on a wide, sandy private beach with breath taking sunsets over the Gulf waters.