
Holiday resort rentals near Anna Maria Island
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Top-rated resort rentals near Anna Maria Island
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Best of Beso Suite Water View ADA 2Balcony/1BR/2BA
Stay in the heart of it all at this one-of-a-kind, unique double unit condo, which boasts views from 2 balconies, has 2 full bathrooms & a private bedroom suite. This upscale, tropical oasis is located right off the Gulf of Mexico’s St. Joseph Sound! RELAX & ENJOY the jacuzzi, dolphin watching & barbecuing, from Beso Del Sol Resort’s Waterfront Guest Pool Deck. Bask in the splendor of Delightful Dunedin’s Premier Resort’s Spectacular Sunset with a complimentary shot from Marker 8 Tiki Bar!

#3-TwinPalms-King Studio Suite
The Studio Suite at our Siesta Key hotel sleeps 1-2. Each room features a king-sized bed, 42-inch TV, dining table as well as a fully stocked stainless steel kitchenette. Perfect for couples or solo travelers. All of our rooms have recently been updated to be as attractive as they are comfortable. The King Studio Suites are furnished in a stylish seaside decor, including a comfortable patio with chairs and umbrella to relax and enjoy the wonderful weather that South Florida has to offer.

Sand Castle Penthouse @CedarCove
The newly renovated Sand Castle Penthouse at Cedar Cove Resort has it all. From the private balcony with panoramic view of the Gulf of Mexico and the private beach, to a full kitchen. This 2br / 2ba penthouse was completely rebooted in 2022 with new floors, furniture and a new luxury spa bathroom in the primary bedroom The second bedroom has a queen size bed with access to another full bathroom from the great room. A queen size sofa bed allows for up to six guests comfortably.

The Sable/Villa#23 (1bed-1bath)
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 with many great eating spots around and close enough to walk to the beach. This offering is an extremely popular 2 bedroom fully equipped condo with dining and living area and a private backyard patio with barbecue grill.

Beachfront Traditional
Located in the Shells building. Enjoy breathtaking sunset views from your large picture window which overlooks Treasure Island’s wide sandy beaches along the Gulf of Mexico. This 297 Sq. Ft. beachfront guest room features (2) Queen Pillow Top Beds. Other features include: * 55” LCD Flat Panel TV * Mini Refrigerator * Microwave * Coffee Maker * Toaster * AM/FM Clock Radio * Hairdryer * Iron, Ironing Board * Electronic Safe * Ceiling Fan * Beach Towels

Adorable Affordable Beach Efficiency
A Beach Adventure Awaits You..Come Play Or Relax @ the Coral Resort Clearwater Beach, Fl This small , lovely island is all water, beaches, restaurants and fun. NO CAR NEEDED. Bike or walk the beach. Visit: Winter the dolphin is right here... White sand will surround you on all these public beaches . Free parking/ internet. Managers onsite. 24 hr Fishing Pier on site. Rent jetski/boats in walking distance. YOLO Note: Unit A5 is a second floor/no elevator.

The Nest, 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 individual Cottages in total that range from a one bedroom units to a three bedroom units.

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.

"The Coconut" at Palm Tree Villas Resort
Enjoy a short stroll to the beaches from the Coconut Villa. We offer a one night stay or a monthly stay. Bring your bicycle and get lost exploring the island. A full kitchen is provides for home cooked meals. This is a ground floor unit that overlooks the swimming pool. One assigned parking space , guest parking available see "Other details to note" on this listing for more info. Holmes Beach VRC24-000021

Suite 1 - Rod and Reel Resort
2 Guests - Queen Bed; Marble European Oversized Shower, Dual Wardrobe and Built-in TV, Keurig Coffee Maker, Hairdryer, Outdoor Refrigerator for Drinks, Complimentary Toiletries, Complimentary Coffee and Condiments, Beach Towels, Spa Robes Secure WI-FI, and Cable Rm Temp Control, Fan, Dual Dark/Light Shades, and Complimentary Bicycles.

Clearwater Beach Collection King Bed 6th Floor B
Relax in comfort in this Mediterranean styled guestroom. During down time enjoy your favorite programs on a flat screen HDTV, or stay connected with friends and family with complimentary wireless internet access. Other amenities important for a comfortable stay include a coffee maker, hair dryer, iron and ironing board.
Popular amenities for resort rentals near Anna Maria Island
Family-friendly resort rentals

The Lookout, with heated pool

Siesta Key Cabana pool side

Grand Suite 6

Suite 4

The Majestic Villa #25

The Nook, with heated pool.

Suite 3

#2-TwinPalms-King Studio Suite
Resort rentals with a pool

The Coconut Villa #22

The Sable at Palm Tree Villas Resort

The Royal Villa #21

Suite 5

Beach house W/Heated Pool across street from beach

Suite 2

The Foxtail/Studio24

Suite 7
Resort rentals with a gym

Bluegreen At Tradewinds - Gulf Front Studio

Bluegreen At Tradewinds - Gulf Front Studio

Bluegreen At Tradewinds - Gulf Front Studio

Tradewinds - Studio Boulevard View

Bluegreen At Tradewinds - Gulf Front Studio

little harbor #305

Tradewinds - Gulf Front Studio

Little Harbor Hideout
Other resort holiday rentals

Bluegreen At Tradewinds - Gulf Front Studio

Tradewinds - Standard Studio Boulevard View

Bluegreen At Tradewinds - Gulf Front Studio

Bluegreen At Tradewinds - Gulf Front Studio

Bluegreen At Tradewinds - Gulf Front Studio

Bluegreen At Tradewinds - Gulf Front Studio

Bluegreen At Tradewinds - Gulf Front Studio

The Queen Villa #20
Quick stats about resort rentals near Anna Maria Island

Total holiday rentals
Explore 30 holiday rentals in Anna Maria Island

Nightly prices starting at
Anna Maria Island holiday rentals start at £118 per night before taxes and fees

Verified guest reviews
Over 250 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Anna Maria Island holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Anna Maria Island rentals

4.9 Average rating
Anna Maria Island stays are highly rated by guests – averaging 4.9 out of 5!
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- Siesta Beach
- Raymond James Stadium
- Crescent Beach
- Busch Gardens Tampa Bay
- John's Pass
- Bean Point Beach
- Coquina Beach
- Turtle Beach
- Anna Maria Island Beach
- Vinoy Park
- Lido Key Beach
- Amalie Arena
- Caspersen Beach
- Tiny House Siesta
- Dunedin Beach
- Cortez Beach
- Sand Key Beach
- Tampa Convention Center
- Jannus Live
- St Pete Beach
- Anna Maria Public Beach
- Hard Rock Casino
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club




