Anna Maria Island Listings

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Monthly Rent $5,500 - $8,000

Absolute Anna Maria-Private Beach Access-Heated Pool-Two Balconies Anna Maria Island, Florida, Listing ID: 28011

Absolute Anna Maria on Anna Maria Island is a tropical paradise offering you seven miles of the most beautiful and peaceful powdery white sand beaches found anywhere in the world. Anna Maria Island is not a place where you go to the beach; Anna Maria Island is a place where you...

  • Condo
  • 1100
  •  2
  •  2

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Gorgeous 4bd/3bath townhome with private pool at Champions Gate Resort Davenport, Florida, Listing ID: 31886

Amazing 4-bedroom, 3-bathroom Townhome at the best resort in Davenport - Champions Gate, sleeps 10 people, all furnished, free Wi-Fi, parking, private pool, BBQ Grill, bed sheets, towels, pack-n-play, highchair, all included. All guests are welcome to use all the resort...

  • Home
  • 1914
  •  4
  •  3

Amazing 4 bd/3.5 bath townhome at Regal Palms Resort Davenport, Florida, Listing ID: 31904

Beautiful 4 bedroom townhouse located in the popular Regal Palms Resort offering great amenities for adult and kids alike - featuring resort pool, lazy river, arcades and its own restaurant. This home has been upgraded recently. Please be aware there is $20 per home per night...

  • House
  • 1856
  •  4
  •  3 1/2

Gorgeous 4bd house with private pool, recently upgraded! Davenport, Florida, Listing ID: 31905

4 Bedroom / 3 Bath – 1,960 sq ft (183 sq meters) Lake Berkley Chic is a ground floor 4-bedroom vacation home located in Lake Berkley Resort in Kissimmee, FL. Within 10 minutes of Walt Disney World, this home is perfect to unwind during your visit to Central Florida. Your...

  • House
  • 1960
  •  4
  •  3
Monthly Rent $2,280 - $2,880

BOAT-FRIENDLY! 3BR Home Sleeps 10 w/Screened HEATED Pool, Pvt Beach Access/Gazebo, Boat Dock Across St., Foosball Table Fort Myers Beach, Florida, Listing ID: 31910

Top Reasons to Book Beach Paradise Getaway: * Private Heated Pool with Screen Enclosure * Completely Renovated * Foosball Table in Entertainment Area * Shared Bay Access with Small Fishing Pier and Tiki Hut Across the Street * 351 Yards to Deeded Beach Access (5 Minute...

  • House
  • 1472
  •  3
  •  2

Downtown Naples paradise Steps from the beach Fully renovated Naples, Florida, Listing ID: 31931

This is Olde Naples living at its best. Steps from 3rd street, walking distance to famous 5th Ave and two blocks from the beach! Available for seasonal or annual rent furnished or unfurnished. Completely renovated. Brand new floors, kitchen, appliances and bathroom. New...

  • Condo
  • 600
  •  1
  •  1
Details No Image Available

$Multi-Month Discount!

Monthly Rent $10,500 - $15,000

2,200 SF 4BR/2BA home with heated pool & lanai, dual living rooms, kids' room with bunk beds, and huge backyard Marco Island, Florida, Listing ID: 31949

Welcome to your perfect Marco Island retreat! This exceptional 2,200 SF 4-bedroom, 2-bathroom single-family home sits on a spacious triple lot, a rarity on Marco Island, ensuring ample privacy and room to unwind. Step inside and discover the luxury of two separate living...

  • House
  • 2200
  •  4
  •  2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $3,800

Midcentury Bungalow in Downtown Orlando. Orlando, Florida, Listing ID: 31960

This warm and clean house is remodeled to the original period it was built. A walk back in time makes this home perfect for reflection and creativity. The living room, kitchen, laundry room, dining area, office space and bathroom are entirely redone to blend midcentury accents...

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  • 1300
  •  3
  •  1

Bahia Lakes Retreat. Spacious Modern Home in a Quiet Friendly Community, with outdoor Grill and Seating. Community pool. Ruskin, Florida, Listing ID: 33317

Step into your dream home, a spacious and inviting two-story house that offers the perfect blend of comfort and convenience. The first floor features a stunning master suite, providing a tranquil retreat for relaxation. Furnished with a California King-sized bed, a nightstand...

  • House
  • 2180
  •  4
  •  3 1/2

Beautiful Gulf Front / Beach Front Longboat Key Condominium Longboat Key, Florida, Listing ID: 33432

This beachfront condo in Longboat Key is a 2 bedroom, 2 bath unit on the 6th floor of the Arbomar Condominiums. An open concept floor plan includes a galley kitchen with SubZero appliances, dining room, and living room that exits to a spacious lanai overlooking the Gulf of...

  • Condo
  • 1200
  •  2
  •  2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $22,000

New construction Pool home with 4 bedrooms and 3 bath close to the beach! Walk or ride to white sandy beaches. Naples, Florida, Listing ID: 33454

New construction close to the beach POOL AND SPA entire house. This 4 bedroom 3 bath home is equipped and turnkey ready for your stay. All you need is your suitcase. The lanai includes an outdoor kitchen with grill, and television. Watch the big game while lounging in the pool....

  • House
  • 1988
  •  4
  •  3
Details No Image Available

$Multi-Month Discount!

Monthly Rent $7,500 - $8,000

Naples 3-bedroom home for seasonal rental Naples, Florida, Listing ID: 33464

Imagine yourself spending winter in this serene, recently renovated 3-bedroom + office home in the prestigious Veronawalk community. This peaceful retreat is perfectly situated on the community's edge, offering privacy with no neighbors behind. Enjoy the expansive heated pool,...

  • Home
  • 1995
  •  3
  •  2 1/2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $3,500

Begin and end each day with views of the Gulf of Mexico Naples, Florida, Listing ID: 33475

Brand new A/C! Fully enclosed garage! Begin and end each day with views of the Gulf of Mexico from this 1481 square foot 2 Bed/2 Bath, renovated, unit in Tower Pointe of Arbor Trace, a highly coveted Senior Living Community. The highly functional kitchen with modern updated...

  • Condo
  • 1481
  •  2
  •  2

2 bd/ 2 ba Completely updated with Marina views and water views to the West Tarpon Springs, Florida, Listing ID: 33493

Screened in Lanai overlooking marina. Upgraded throughout. No carpet. Open kitchen with granite countertops. Drawer pull outs. Appliances purchased 2/2024. Washer and dryer full size in unit. Large walk-in closet in master with closet organizers. Master has 2 sinks, drawers. 2...

  • Condo
  • 1065
  •  2
  •  2
Monthly Rent $3,750 - $5,100

Mermaid Wishes Englewood, Florida, Listing ID: 33509

This beautifully furnished home in Englewood has an open floor plan and well-equipped kitchen. The open design allows you to stay connected to family while cooking or use the grill on the lanai to make dinner. The table in the dining area seats six. The master bedroom with...

  • House
  • 1800
  •  3
  •  2
Monthly Rent $1,950

Upscale Brand New 500 Sq Foot Home 25 Minutes from Disney Orlando, Florida, Listing ID: 33567

Please email me if you want to see pictures; the website was malfunctioning. We are in the city of Orlando in a wonderful, quiet neighborhood. It is only one mile away from the grocery stores, shopping, restaurants, and the delicious 1908 Bakery. 25 minutes from Disney...

  • House
  • 500
  •  1
  •  1
Details No Image Available

$Multi-Month Discount!

Monthly Rent $2,800 - $3,200

One bedroom condo over looking the intercoastal and a five minute walk to sunset beach and Caddy's Beach bar!! Treasure Island, Florida, Listing ID: 33588

This comfortable 1-bedroom, 1-bathroom is located on the intercostal waterway, with easy access to the beach. It is tastefully decorated throughout with a newly remodeled bathroom and fully equipped kitchen. There is a washer and dryer inside for your use, has a private balcony...

  • Condo
  • 750
  •  1
  •  1
Monthly Rent $2,400

Completely remodeled condo! Bonita Springs, Florida, Listing ID: 33589

Nestled between S Tamiami Trail 41 and Old 41 Road, with access to all things Florida you also find perfect seclusion and privacy in this gem! Just minutes from shopping, grocery, and restaurants but also the beach and there are many to choose from. Completely remodeled unit,...

  • Condo
  • 0719
  •  1
  •  1
Details No Image Available

$Multi-Month Discount!

Lake View Dream Villa is a detached 5 bedroom ,2 story Villa with private swimming pool overlooking the Lake. Davenport, Florida, Listing ID: 33593

Lake View Dream Villa is a 2 storey Villa with a stunning private swimming pool overlooking the Lake . Vaulted ceilings and full sitting room full kitchen Breakfast bar and Full formal dining area 5 bedrooms including a King master suite and a Queen master suite on the...

  • Villa
  • 2400
  •  5
  •  3
Details No Image Available

$Multi-Month Discount!

Monthly Rent $3,900

Looking for a cozy and modern place to call home just minutes from the beach? Estero, Florida, Listing ID: 33613

Experience Bonita Springs/Estero in this bright refreshed 2-bedroom 2-bathroom condo with gorgeous views of the lake. Located in a stunning private gated community just 19 minutes from Fort Meyers airport, and 13 miles from the beach, you can enjoy the...

  • Condo
  • 1192
  •  2
  •  2
Monthly Rent $3,500

WELCOME TO YOUR BEACHFRONT DREAM CONDO Madeira Beach, Florida, Listing ID: 33618

WELCOME TO YOUR BEACHFRONT DREAM CONDO, with amazing views, directly on the Gulf of Mexico. Imagine waking to the soothing symphony of waves, from your large bedroom balcony. This condo offers two large bedrooms, each with their own bath & walk-in closets. Every corner of this...

  • Condo
  • 1100
  •  2
  •  2
Monthly Rent $5,500

Vacation Home Near Beach with all amenities. Fully remodeled home in a perfect location. Largo, Florida, Listing ID: 33622

The space has 3 bedrooms with solid core doors which are a great sound barrier. The house has been fully renovated and pool was recently built. We also created an outdoor dining lounge area for you to enjoy. Guest will not have access to our garage since it is used for storage...

  • Home
  • 1700
  •  3
  •  2
Monthly Rent $90,309,033

FLORIDA WEST COAST HIGH SEASON SPECIAL! GOLF AND BEACH LOVER'S DELIGHT SPACIOUS LARGE END UNIT 2BD/2Bath w/Den FAB VIEWS Bradenton, Florida, Listing ID: 33629

FLORIDA WEST COAST HIGH SEASON SPECIAL! GOLF AND BEACH LOVER'S DELIGHT! SPACIOUS LARGE END UNIT 2BD/2BATH w/Den SWEEPING SUNSET VIEWS MINUTES FROM ANNA MARIA ISLAND BEACHES 100 STEPS FROM PINEBROOK GOLF CLUB PRO SHOP FULL SEPARATE MASTER AND GUEST SUITES LARGE WALK IN...

  • Condo
  • 1575
  •  2
  •  2
Monthly Rent $5,673 - $7,750

3-bedroom, 2.5-bath Port Charlotte vacation rental. Fully furnished with private fence and pool, and mini orchard. PORT CHARLOTTE, Florida, Listing ID: 33635

A Charming European style home that you will be able to relax and enjoy as your home away from home. This home is tucked into a residential neighborhood, with a Privacy fence, pool and mini- orchard for your enjoyment. This sunny, one-level space positions you just minutes...

  • House
  • 2300
  •  3
  •  2 1/2
Monthly Rent $2,175

Nestled in the park-like community of Golden Gate, Aqua Bay Apartments is conveniently located minutes to I-75, Naples, Florida, Listing ID: 33637

Nestled in the park-like community of Golden Gate, Aqua Bay Apartments is conveniently located minutes to I-75, just 7 miles from the world famous beaches of Naples and a short drive to the best shopping and dining on the west coast of Florida. Aqua Bay is an apartment...

  • Apartment
  • 850
  •  1
  •  1
Details No Image Available

$Multi-Month Discount!

Monthly Rent $6,500 - $7,500

3-month or more rental discounts available. Cape Coral, Florida, Listing ID: 33639

Beautifully newly built home with heated pool and spa and canal with gulf access. House located close to beautiful Burnt Store Marina (2 miles from home). Fish from your own dock! Open area game-room/entertainment area with pool table, chess ping pong, foosball, smart TV,...

  • House
  • 3760
  •  4
  •  3

2 bed/2 bath Fort Myers Beach Oceanfront Condo Fort Myers Beach, Florida, Listing ID: 33658

This exquisite 4th Floor, 2 bed/2 bath unit at the sought after THE PALMS of Bay Beach complex, is so tastefully decorated with beautiful contemporary furnishings it will absolutely WOW you the moment you walk through the door. The pictures and video are definitely proof. The...

  • Condo
  • 1024
  •  2
  •  2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $2,500

Property is located in an upscale gated ranch community. It is a guest house. It has access to a pool. Ocala, Florida, Listing ID: 33662

House located in an upscale gated ranch community. Property is 5 acres with beautiful landscaping with green lush land. There is 4.5 miles long walking/biking/horse trail within walking distance. Tenant will have access to a large swimming few feet in distance from the house.

  • Home
  • 1500
  •  2
  •  2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $4,600

Luxury Updated Reunion Resort Condo. Pool view from Terrace. 15 Min from Disney. Kissimmee, Florida, Listing ID: 33914

Decorated in a Hollywood Studio style design, this newly renovated condo is located in Reunion Resort near 3 signature golf courses ( Nicklaus, Palmer and Watson) The condo is furnished with high end appliances, granite countertops, high ceilings and a wraparound covered patio....

  • Condo
  • 1450
  •  3
  •  2
Monthly Rent $3,450 - $5,400

Land's End 4-404 Bay Front - Premier Treasure Island, Florida, Listing ID: 33972

**Please note that due to damage from Hurricane Helene, this property temporarily has no access to the elevator, pool, or amenities. At this time, we do not have a guaranteed date for this to be accessible, though to our knowledge this should not impact 2025 stay dates. Please...

  • Condo
  • 1100
  •  2
  •  2
Monthly Rent $3,750 - $5,700

Land's End 9-404 Beach Front - Premier Treasure Island, Florida, Listing ID: 33973

**Please note that due to damage from Hurricane Helene, this property temporarily has no access to the elevator, pool, or amenities. At this time, we do not have a guaranteed date for this to be accessible, though to our knowledge this should not impact 2025 stay dates. Please...

  • Condo
  • 1100
  •  2
  •  2
Monthly Rent $3,300 - $3,750

Beach Quarters #4 Gulfport, Florida, Listing ID: 33974

Top Reasons to Book: * 173 Yards to the Gulfport Beach Recreation Area * 5 Miles to St. Pete Beach * Pet Friendly up to 20lbs. (Additional Cost Applies) * On-Site Parking and Laundry Facility * Walking Distance to many Restaurants, Art Galleries, and Boutiques * Professionally...

  • Condo
  • 600
  •  1
  •  1
Monthly Rent $2,430 - $3,270

Amadeus 7 Treasure Island, Florida, Listing ID: 33975

**Please note that due to damage from Hurricane Helene, this property temporarily has no access to the pool. At this time, we do not have a guaranteed date for this to be accessible. Please reach out with any questions. Rates lowered!** Top Reasons to Book: •Walking...

  • Condo
  • 700
  •  1
  •  2
Monthly Rent $3,000 - $4,170

Barefoot On The Shores II Indian Shores, Florida, Listing ID: 33976

**POOL CLOSURE CURRENTLY SCHEDULED FOR SEPTEMBER 4th and 5th, 2024. This could vary** Top Reasons to Book this Gorgeous Condo: * Beach Access Located Across the Street * Newly Renovated, Ground Floor Unit * All the Amenities: Well Maintained, Seasonally Heated Pool + Large...

  • Condo
  • 735
  •  1
  •  1
Monthly Rent $3,000 - $3,720

Crystal Palms 201 Treasure Island, Florida, Listing ID: 33977

**Please note that due to damage from Hurricane Helene, this property temporarily has no access to the elevator, pool, front lobby, or beach access. At this time, we do not have a guaranteed date for any of these to be accessible. Please reach out with any questions. Rates...

  • Condo
  • 925
  •  2
  •  2
Monthly Rent $ 6,330

Madeira Del Mar 205 Madeira Beach, Florida, Listing ID: 33978

**Please note that due to damage from Hurricane Helene, this property temporarily has no access to the elevators or pool. At this time, we do not have a guaranteed date for these to be accessible, but we do not anticipate any interference with 2025 stay dates. Please reach out...

  • Condo
  • 1600
  •  3
  •  3
Monthly Rent $4,800 - $6,270

Mirada Manor St Petersburg, Florida, Listing ID: 33979

Top Reasons To Book This Gorgeous Home: * Spacious 2-Story Home with Garage * Outdoor Patio and Balcony with Great Views * Bikes for Guest Use Available * Heated Pool, Large Pool Deck and Hot Tub * Close Proximity to the beach AND Ft Desoto State Park * Picturesque...

  • House
  • 1320
  •  3
  •  2
Monthly Rent $2,700 - $2,790

Royal Orleans 117 Redington Beach, Florida, Listing ID: 33980

Top Reasons to Book! • First floor unit with easy pool access! • Short and convenient walk to the sand! • Relaxing pool with sun loungers! Introducing The Royal Orleans, a charming one-bedroom, two-bath condo unit #117 that offers a tropical oasis on the first floor....

  • Condo
  • 500
  •  1
  •  2
Monthly Rent $3,450 - $5,280

Blue Beach Cottage Redington Beach, Florida, Listing ID: 33981

Top Reasons to Book This Awesome Coastal Cottage: * The Beach is Across the Street - Short, Convenient Walk * Spacious Layout, Luxurious Furnishings, Plenty of Room for All * Additional Outdoor Seating for Gathering, Dining and Relaxation * Fenced Backyard with Grill *...

  • House
  • 1350
  •  3
  •  2
Monthly Rent $4,620 - $6,120

Island Nature Retreat Fort Myers Beach, Florida, Listing ID: 33991

Top Reasons to Book this South End Home: * Canal Front Home with Private Pool * Screened in Lanai with Built-In Bar and Outdoor Furniture * Less than 1 mile to Beach Access #11 * 4.5 miles to Times Square * Professionally Managed Welcome to Island Nature Retreat,...

  • House
  • 1170
  •  2
  •  2
Monthly Rent $14,460 - $16,140

The Big Blue Fort Myers Beach, Florida, Listing ID: 33992

Top Reasons to Book this Adorable, Charming Home: * Canal Front with Relaxing Water Views * Beautiful Back Porch with Dining Space for 6 * Lush Landscaping - Perfect for Privacy * Private Boat Dock * 528 Yards to Beach Access #11 * 4 Miles from Times Square *...

  • House
  • 1012
  •  2
  •  1 1/2
Monthly Rent $3,330 - $4,410

Aqua Oasis Fort Myers Beach, Florida, Listing ID: 33993

Top Reasons to Book Aqua Oasis: * Canal Front with Private Boat Dock * Updated, Modern Interior with High-End Touches * 438 Yards to Public Beach Access #16 * 3 Miles to Times Square * Professionally Managed Welcome to Aqua Oasis. You will love the pure beauty and...

  • House
  • 1300
  •  2
  •  2
Monthly Rent $5,310 - $6,930

Palmview Paradise Fort Myers Beach, Florida, Listing ID: 33994

Top Reasons to Book this Beautiful Canal Front Home: * Canal Front with Private Pool * Bring Your Kayak and Paddleboard * All Brand New Furnishings (2024) * YouTube on all TVs * Less than 1 mile to Beach Access #11 * 4.5 miles to Times Square * Professionally...

  • House
  • 1570
  •  3
  •  2
Monthly Rent $5,370 - $8,280

Ibis Landing Fort Myers Beach, Florida, Listing ID: 33995

Top Reasons to Book Ibis Landing: * South End Canal Front 3 Bedroom Home * Private Heated Pool and Dock * All New Furnishings as of 2024 * YouTube on All TV’s * 495 Yards to Beach Access #11 * 3.5 Miles to Times Square * Professionally Managed Come experience Ibis...

  • House
  • 1568
  •  3
  •  2
Monthly Rent $5,460 - $6,660

Flight of Albatross Fort Myers Beach, Florida, Listing ID: 33996

Top Reasons to Book Flight of Albatross: * Gorgeous Brand-New South End Home * Private Pool with Spill Over Spa and Thatched Tiki Hut * Canal Front – Bring your Kayak and Paddle Board * 0.6 Miles to Beach Access #11 * 4.2 Miles from Times Square * Professionally...

  • House
  • 2125
  •  3
  •  3
Monthly Rent $2,100 - $2,880

Sunsational Sunsets Fort Myers Beach, Florida, Listing ID: 33997

Top Reasons to Book Sunsational Sunsets: * Stunning Private Pool Overlooking the Canal * Outdoor Covered Bar with Lounge Area and Grill * Beach Essentials (Beach Chairs, Wagon, and Towels) * Pet Friendly (Under 30lbs, Additional Fee Applies) * 302 Yards to Beach Access 33...

  • House
  • 2683
  •  5
  •  4
Monthly Rent $ 3,000

MT Beach Nik #2 Fort Myers Beach, Florida, Listing ID: 33998

Top Reasons to Book at Mermaid Tales: * Shared Complex Pool with Spill Over Spa * Beach Chairs Available on First Come, First Serve Basis * Pet Friendly for Dogs Under 30lbs (For an Additional Fee) * 530 Yards to Beach Access #27 * 0.9 Miles to Times Square *...

  • Multi-Family
  • 522
  •  1
  •  1
Monthly Rent $3,360 - $4,230

Waterside Penthouse #3H1 Fort Myers Beach, Florida, Listing ID: 33999

Top Reasons to Book Waterside Penthouse #3H1: * Views of the Gulf of Mexico * Community Lagoon Style Pool and Hot Tub * Enjoy Onsite Sauna, Fitness Center, Tennis Courts, BBQ and more * 0.6 Miles to a Private Beach Access for the Community * 5.5 Miles to Times Square *...

  • Condo
  • 1405
  •  2
  •  2
Details No Image Available

$Multi-Month Discount!

Enjoy Sunset Views Over The Gulf of Mexico Marco Island, Florida, Listing ID: 34019

Enjoy sunset views over the Gulf of Mexico every night of the year from the spacious, beautifully furnished living room. Formal dining area with a beautiful built-in Buffet for entertaining. Lovely appointed kitchen offering a hooded induction range and breakfast bar. A large...

  • Condo
  • 1445
  •  2
  •  2