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Southwest Vacation Rentals

(3270 rentals)
Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 2 miles to Clam Pass

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Location, location and everything you could ask for at this beautiful, centrally located condo in the most convenient location in all of Naples. Truly a gem, this condo enjoys tranquil western facing sunset views and quiet nature where you can watch golfers putt on the green at the Quail Run Golf Course....

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Featured review

"March in Emerald Greens"

My husband and I just returned from spending the month of March in this condo.The unit itself is clean and stocked with everything you would need. The location is perfect and the sunsets off the lanai are...

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$115
avg per night
New
Bradenton Condo
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Escape to your luxurious coastal retreat overlooking the shimmering waters of Palma Sola Bay. This coveted 3rd-floor, 3 bedroom, 2.5 bathroom, turnkey-furnished condo offers the perfect blend of comfort, style, and serenity, with two private balconies capturing sunrise over the pond and golden Gulf sunsets...

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$169
avg per night
Punta Gorda House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Pool

About this property

QUINTESSENTIAL FURNISHED RENTAL IN SW FLORIDA* WATERFRONT WITH DOCK * HEATED POOL AND SPA * 2-BEDROOMS, 2-BATH WITH CARPORT * WATER VIEWS * TOTALLY UPDATED * NEWER APPLIANCES * TASTEFULLY FURNISHED * IDEALLY LOCATEDTurnkey Furnished Seasonal Rental in Punta Gorda Isles with Deeded Dock...

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$133
avg per night
Cape Coral House
Sleeps 10, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Sunshine Cove welcomes you to beautiful SW Florida! Our home is centrally located, close to restaurants, shopping, beaches, eco preserves, & so much more! Relax in our spacious lanai & enjoy our heated pool with a removable safety fence. Come hang out in our garage game room & play air hockey,...

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Featured review

"Sunshine Cove was a beautiful home and a great place to relax, in a quiet neighborhood!"

The home was exactly as shown! The kitchen was well stocked to meet our every need. The pool and lanai were amazing and perfect for evening swims for our grandchildren! Would stay here again!

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$145
avg per night
Fort Myers Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 5 miles to Ft Myers

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Summer and fall dates available!Not too early to book for 2027!Enjoy this private, end unit, 2 bed 2 bath, 2nd floor condo in beautiful Fort Myers. We are ready to welcome you for your getaway! We allow weekly, monthly, or seasonal rentals. Book Direct to save on platform fees! Discounts apply...

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Featured review

"Great location"

We enjoyed every minute of our stay! The Condo was clean and inviting! There's a covered Lanai to sit on which was great at night and morning coffee. Short drive to Fort Myers beach and walking distance...

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$109
avg per night

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Bonita Springs House
Sleeps 1, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

!!**AVAILABLE SEASON 2026!! ***Spacious 3 Bedroom + Den and 3 Full Baths home with Heated Pool & Spa on an oversized lot. This property is close to shopping, restaurants, beaches and wonderful historic Bonita Springs. Enjoy new kitchen upgrades to satisfy your inner chef. Take part in the tranquil...

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$117
avg per night
Bradenton House
Sleeps 8, 3 bedrooms, 2 bathrooms
104 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Escape to sunny Florida and enjoy your own private retreat in Bradenton. This beautifully remodeled 3-bedroom bungalow combines the comfort of home with the fun of a vacation getaway — featuring a private saltwater pool, spacious indoor living areas, a family-friendly game room, and a convenient...

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$178
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Unwind in this bright and breezy 2-bedroom, 2-bath condo just steps from the beach. Sip your morning coffee on the private balcony with peekaboo Gulf views, then head straight to the sand, shops, and dining — all just minutes away.Perfect for couples, families, or friends, this coastal retreat...

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$217
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Welcome to your beachfront escape at Fisherman's Cove on beautiful Turtle Beach, Siesta Key.This colorful and inviting first-floor condo comfortably accommodates up to six guests and offers the convenience of direct beach access just steps from your private lanai. Relax in the comfortable patio...

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$238
avg per night
Rotonda West Bungalow
Sleeps 6, 3 bedrooms, 2 bathrooms
14 reviews

Distance to beach: 5 miles to Englewood Lemon Bay

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Heron's Way is perfect spot for relaxing holiday, yet close to the best beaches, golf courses, nature trails and shopping malls in the South West. It is situated in a tree lined road, on a freshwater canal which attracts an abundance of wildlife. Minimum of passing traffic, just the sound of birdlife...

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Featured review

"Another Wonderful Stay!"

Another Wonderful Stay!Just returned from a fantastic 2-week stay at this beautiful Florida villa—our third time visiting, and it never disappoints! The villa was spotless and extremely comfortable,...

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$173
avg per night
Fort Myers Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Two bedroom, two bath, non-smoking Heritage Pointe condo on the third floor with beautiful and relaxing lake views on the screened in lanai to enjoy a cup of coffee or glass of wine. Elevator access. Heritage Pointe has a wonderful clubhouse where there are many scheduled activities, heated resort style...

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Featured review

"Excellent condo rental"

This condo at Heritage Pointe has all you need for a comfortable 2 months stay. There is a well equipped kitchen and a comfortable lounge with a large television, a sofa and two reclining chairs. The...

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$68
avg per night
Sarasota Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautifully remodeled unit with spectacular gulf views from your 2nd floor lanai. Bamboo and tile floors throughout and an updated kitchen fully equipped with granite countertops. Freshly painted with two new remodeled bathrooms. Upgraded Internet XFINITY bundled with three flat screen Smart TV's...

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$238
avg per night
Rotonda West House
Sleeps 6, 3 bedrooms, 2 bathrooms
19 reviews

Distance to beach: 9 miles to Boca Grande, Englewood Beach & Manasota Key

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Fully loaded...includes beach chairs, umbrellas, coolers, beach towels, grill...just bring your clothes, food, drinks and sunscreen!BEAUTIFUL AND CLEAN 2,100 sq. ft. home in Rotonda West INTERNET & CABLE TV MOVIES AND GAMES available HEATED POOL w/built-in pool bench PRIVATE WOODED BACKYARD LANAI...

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Featured review

"A Perfect Florida Escape — We’ll Definitely Be Back!"

Making our arrangements with Linda could not have been easier. She was very friendly and helpful and made us comfortable with the transaction from the very start. The moment we arrived, the home itself...

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$181
avg per night
Bonita Springs Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 5 miles to Bonita Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Quiet property located in Bonita Bay gated community overlooking lake, golf course, and tropical preserve. Wild Pines is noted for its tranquil setting, convenience to shopping and restaurants, and unique availability for weekly rental in Bonita Bay. For these reasons and more, our Wild Pines condo has...

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Featured review

"Comfortable and relaxing"

This condo met every requirement we had for a laid-back getaway for my husband and me. The bed was comfortable, the layout was efficient, the neighbors were quiet and respectful. We enjoyed sitting by...

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$154
avg per night
New
Cape Coral House
Sleeps 9, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Swaying Palms Relaxed Comfort in SE Cape CoralGet ready to unwind at Swaying Palms, your stylish and sun-soaked getaway in the heart of SE Cape Coral. This spacious 3-bedroom, 2-bathroom pool home offers everything you need for a fun-filled family vacation, a couples' retreat, or a...

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$271
avg per night
Fort Myers Beach House
Sleeps 6, 3 bedrooms, 2.5 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The Whitehouse is a waterfront home offthe main road of Estero Boulevard. It features a large deck overlooking the pool/canal,relaxing views of Estero Bay and the canal, a privateheated oversized pool, wireless internet access, and boatdock with lift and kayak/canoe entry slip. Canoe...

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Featured review

"Very nice house for a relaxing month on FMB"

We stayed for the month of March 2025. The online description of the house was accurate. It is very nice! Living area was very comfortable. Kitchen is great and stocked with nice dishes, cooking pans and...

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$273
avg per night
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 0.5 miles to Walk to Pelican Bay private beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Experience the best of Naples living in this beautifully renovated 2-bedroom, 2-bath condominium in Serendipity at Pelican Bay for just $10,000/month in-season. Offering approximately 1,300 square feet of bright, comfortable living space, this second-floor residence features vaulted ceilings, abundant...

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$170
avg per night
Naples Villa
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 3 miles to Vanderbilt Beach

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Nicely decorated villa in Stonebridge which is a gated, private golfing community with lush landscaping and walking and bicycling paths. The owners' membership can be transferred to the tenant which gives the tenant full privileges to the Stonebridge amenities for a small transfer fee. The Club House...

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$121
avg per night
Punta Gorda Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Lease this Luxury Birkdale, 2-bedroom, and 2-bathroom, on the desired top floor of the Terrace Condominiums; located in the beautiful, secured with gated entrance at Heritage Landing.Heritage Landing is a brand-new Golf Country Club Community in the beautiful Punta Gorda, Florida. Current amenities...

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$77
avg per night
Fort Myers Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful apartment in a very quiet neighborhood. We have pickle ball and tennis courts, two pools (one is heated), volleyball and basketball court. Outdoor grill areas. It is a pet friendly community and 2 pets per apartment are allowed. We have Bingo nights, family days and pool parties.

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$76
avg per night
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Vanderbilt beach

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Experience relaxed, resort-style living in this bright 2BR/2BA second-floor condo in Ventanas at Tiburón at $8,500/month in season. The open-concept great room and spacious kitchen are perfect for entertaining, while both bedrooms feature en-suite baths. Step out onto the large, screened lanai...

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$169
avg per night
Punta Gorda Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Available and with special pricing for 2027….Don’t wait - book direct with the owner!!Resort style living awaits you at Lennar's Heritage Landing Golf and Country Club in Punta Gorda, FL. This recently built 2nd floor condo is fully furnished with 2br/2ba and enjoys spectacular views...

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Featured review

"Paradise"

We throughly enjoyed our stay. The condo was outstanding and the area was fantastic. The amenities were great and all the people we met. I would definitely recommend Heritage Landing to anyone looking for...

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$84
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Welcome to a bit of heaven!A gorgeous gulf-front vacation awaits you as you come and enjoy this enchanting condo! Located directly on beautiful Turtle Beach in Siesta Key and just steps away outside your door. There is no other resort complex like this that is so close to the beach!As you travel...

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$238
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Bougie Bay, a beautiful renovated ground-floor condo located in the sought-after Runaway Bay community. This unit is just steps across the street from the breathtaking Gulf beaches of Anna Maria Island. This bright and stylish 2-bedroom, 2-bathroom unit has been completely updated with modern furnishings,...

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$129
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Indulge in the ultimate beach escape to “Mary’s Place” located on Los Cedros, a *premier location* just north of Pine Avenue in the city of Anna Maria. Mary’s Place is a very short walk to the gorgeous, white sandy beaches of Anna Maria Island. This *ultimate beach house* has been...

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$424
avg per night
Naples House
Sleeps 6, 3 bedrooms, 2.5 bathrooms
4 reviews

Distance to beach: 14 miles to Marco Island or Naples

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Our home "Pelican" is brand new and has just been finished and finally furnished in September 2015. It offers 3 bedrooms (sleeps 6) plus a den, 2.5 baths and a private heated pool on a total living area of 2233 sq ft . It is furnished to a high standard and fully equipped with all the essentials...

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Featured review

"Perfect home for South Naples"

Nice big home with a screened in pool. Close to Marco Island and just a short drive to Naples Center. Jurgen, the owner, is great and so accommodating!

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$171
avg per night
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 6 miles to 5th ave

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This is a ground floor condo, 2 bedroom, 2 bath fully furnished with over sized garage located in Falling Waters which is centrally located between Marco Island and downtown Naples.Falling Waters Beach Resort has two pools, two tennis courts and one boccie court. One pool is a heated 600 foot lazy...

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Featured review

"I do not understand??"

Hallo We are 2 persons and want a Apartment with 1 or 2 bedrooms about Naples fore middle Januar for 4 /6 weeks. What can you offer fore us? Best regards Birte and Eckhard Schmidt Bremen Germany

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$67
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Top Reasons to Book Crazy Mermaid • Waterfront canal views throughout the home • Private pool (heated upon request for additional fee) • Private dock for relaxing or fishing • Screened porch overlooking pool & water • Spacious 4BR layout for groups & families •...

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Featured review

"Two Thumbs Up"

This place was so fun and worked great for our family. Plenty of beds, lots of room to hang, and provided just about everything you needed. The pool and dock were a fun extra! We plan to come back!!

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$226
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

A211 is gorgeous, newly renovated with brand new kitchen, appliances and cabinets, living room, dining room and bathrooms (all with new walls, ceilings, doors and tiled floors). Also available is a new in-unit large capacity washer and dryer. The kitchen is fully equipped with many of the comforts of...

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$238
avg per night
Cape Coral House
Sleeps 8, 3 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 25 miles to Fort Myers Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Property Highlights: • Heated solar pool overlooking the canal (cost included) • Private dock & boat lift – bring your boat! • Covered poolside lanai w/ customizable string lights • Arcade + game room (fun for kids & adults!) • 3 bedrooms / 2 baths with new...

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Featured review

"Perfect Pelican Neighborhood Retreat"

Though I didn’t stay here myself (I sold the property to these amazing hosts), I can vouch for their flawless setup. Every detail screams thoughtfulness—from plush comforts to top-notch entertainment...

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$230
avg per night
Naples House
Sleeps 11, 4 bedrooms, 4 bathrooms

Distance to beach: 0.3 miles to Vanderbilt Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This property has over 200 5 star reviews on other well known vacation websites. We are advertising this property here as an alternative to the other vacation websites.Closest To Beach Main House & Separate Villa 4 Bdrm , Huge Pool. Walk To Beach Best Value In Naples: We are local year round...

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$269
avg per night
Sarasota Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This 2nd floor unit has been completely remodeled with sophistication. Spend your vacation with a superb Gulf View while reclining on new leather and wicker furnishings and watching the large flat screen wall mounted TV. Gorgeous tile throughout and a brand new kitchen with stainless appliances and...

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$238
avg per night
Bradenton House
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

NEW MANAGEMENT!!! Tucked away in sought-after Northwest Bradenton, this cheerful canal-front retreat is all about easy Florida living—where sunny days, calm waters, and laid-back coastal vibes come together. With a private dock, direct Gulf access, and peaceful water views right out back, it’s...

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$197
avg per night
Naples House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

New and Renovated home with all new furniture 2 large living rooms TV and Internet 4 bedrooms with 6 beds A huge swimming pool and outdoor furniture Full kitchen Laundry Garage for vehicle parking Clubhouse close with a swimming pool, hot tub, and fitness center Close to Dunkin Donuts,...

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$264
avg per night
Anna Maria Island Apartment
Sleeps 3, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to “Barefoot Mermaid 4” a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft to white powder sand beaches of the Gulf of Mexico and less than a few flip flop...

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Featured review

"Perfect location."

Perfect 1-bedroom apartment, only a steps away from the beach! Perfect location within walking distance to everything on Pine Street.

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$209
avg per night
Cape Coral House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Cozy SW Cape Coral Retreat with Pool, Hot Tub & Garden View - Sleeps 6 | 3 Bedrooms | 2 Bathrooms- 1 King Bed + 2 Queen Beds- TVs in Master & Living Room- Family-friendly with baby crib & high chair- Utilities includedWelcome to your relaxing getaway in one of the most...

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$225
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • WiFi

About this property

Welcome to "A Wave From It All" – your perfect retreat on Holmes Beach, Anna Maria Island, FL. Nestled within a charming triplex, our end unit offers front-row views of the Gulf of Mexico, ensuring a truly unforgettable stay. With its unbeatable location, spacious accommodations,...

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$225
avg per night
Punta Gorda Villa
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

A True Gem at Heritage Landing - Luxurious 1st Floor Veranda Experience the epitome of Florida living in this stunning 2-bedroom + den, 2-bath veranda, complete with a social membership. This spacious home seamlessly blends elegance with comfort, offering an unparalleled lifestyle in one of the most...

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Featured review

"A wonderful, beautifully decorated condo At Heritage Landing."

A wonderful, beautifully decorated condo at Heritage Landing. We enjoyed all of the amenities and loved our stay!

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$109
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
97 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • WiFi

About this property

True Beachfront Escape + Elevator + Hot Tub + Golf Cart | Serendipity Anna MariaWelcome to Serendipity, your pet-friendly beachfront sanctuary on the coveted north end of Anna Maria Island — where quiet mornings, spectacular sunsets, and the rhythm of the Gulf create the perfect island escape.Perfectly...

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$1,052
avg per night
Naples House
Sleeps 6, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Luxury 3 bedroom, 3 bathroom home on an over-size corner plot right on the golf course. 15 five-star reviews on VRBO, this account I've just transferred to Florida rentals. 3 samples of the reviews are quoted.Enjoy a quiet sun-downer on the large patio with swimming pool and Spa ,sun-loungers,...

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Featured review

"Beautiful, private home in paradise!"

We rented this spectacular home in March of 2019 and again in March of 2021. We have rented other homes in Lely Resort, but nothing compares to this one. The location is perfect--close to the amazing...

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$330
avg per night
Cape Coral Villa
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Moondance Villa – Waterfront Bliss in Cape Coral ??? Highlights- Sleeps 6 | 3 Bedrooms | 3 Bathrooms- Private heated pool with canal views- Waterfront patio & tropical garden- Outdoor bar, lounge & multiple TVs- Pool table, BBQ grill & outdoor dining- Fully equipped...

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$365
avg per night
Anna Maria Island Townhome
Sleeps 6, 3 bedrooms, 3.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Turtle's Bay by Beach Retreats Vacation Rentals 306 Clark Dr Unit B, Holmes Beach, Anna Maria Island VRC17-000006 3 Bedrooms | 3.5 Bathrooms | Sleeps 6 | Heated Pool ​​​​​​​ Pet Friendly This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighborsDog...

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Featured review

"Beautiful Property"

Visiting Anna Maria Island was amazing!! The weather was beautiful and the home was beautiful too!! I would definitely come back to visit this area.

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$390
avg per night
Fort Myers Beach Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to Lovers Key Beach Club, featuring 9 condos to choose from! Relax on our private beach getaway. Enjoy ocean views, with glorious sunrise and sunsets. Our condos accommodate up to four guest. With large king size beds, and pull out couches. You'll also find kitchens equipped for your cooking...

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$194
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

VRC17-000063 Welcome to “Coastal Breeze” on beautiful Anna Maria Island. This vibrant four-bedroom, three-bathroom island retreat is your perfect vacation escape on AMI. The backyard is a true highlight, featuring a private heated pool with spa, cozy and colorful seating areas, and a one-of-a-kind...

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$479
avg per night
Punta Gorda Condo
Sleeps 4, 1 bedroom, 1 bathroom
4 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

AVAILABLE, WEEKLY, BI-WEEKLY-MONTHLY......Come enjoy your Marina get-away condo in popular Burnt Store Marina. Turnkey furnished condo within a short walk to the Marina Yacht Basin with fabulous views of marina life and evening sunsets. Beautiful 1 Bedroom/1bath with tile flooring throughout, plus enclosed...

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Featured review

"Quiet condo right on the marina!"

Nice quiet location with really good restaurant across street from the condo. Condo was clean and well stocked. I will definitely stay here again.

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$125
avg per night
Marco Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 0.3 miles to 1/4 mile walk to public beach access

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Spacious 2 bedroom 2 bathroom fully furnished condo with an awesome balcony view of the pool area and ocean in the background. Cable TV in living room, master bedroom and guest bedroom. The place is equipped with a walk in kitchen, two walk-in closets, a washer and dryer, and a sleeper sofa. Can see for...

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Featured review

"Wonderful location, quiet neighborhood. View from lanai awesome. Condo neat, clean and well equipped."

The Sands is a great place to stay. Easy walk to beach, restaurants, shops, and theater. Plenty of parking space available. The grounds, pool and hot tub were well kept. Even had cute burrowing owls in...

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$120
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Top Reasons to Book: -Only 1.5 Blocks to the Beach -Private Pool with Swim-Up Tiki Table (Free Pool Heat in Cooler Months) -3 Bedrooms + Sleeper Sofa – Sleeps Up to 6 -All Bedrooms Have Ensuite Bathrooms -Fully Equipped Kitchen with Island Seating -Multiple Outdoor Spaces Including Front Deck...

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$258
avg per night
Cortez Cottage
Sleeps 5, 2 bedrooms, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner

About this property

Wake to sparkling views of Sarasota Bay from both the front and back view of this cozy light filled 2 bedroom, 1 bath vacation cottage fully furnished retreat has everything you need for a relaxing stay. Outside, gather around the firepit facing the bay-the perfect spot to enjoy sunsets, or a glass of...

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Featured review

"awesome stay"

Vicky and her family went out their way to accoadate us. We loved the house and the neighborhood. The sunsets are amazing.

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$207
avg per night
Longboat Key Condo
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Newly renovated & furnished 1/1 second floor condo with wonderful view of Bishops Bayou on the uncrowded north end of Longboat Key. Whitney Beach has a beautiful natural stretch of beach as well as many amenities including tennis / pickleball courts, swimming pools, shuffleboard & boat docks...

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$333
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
77 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Bayfront Pool Retreat + Walk to Pine Ave + Golf Cart | TripletailWelcome to Tripletail, your bayfront escape on the coveted north end of Anna Maria Island — where peaceful waterfront views, walkability to Pine Avenue, and resort-style outdoor living come together for an unforgettable stay.Perfectly...

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Featured review

"Paradise by the sea!"

Beautiful, outstanding home with unbelievable views from every window! The water is right outside your door. Plus there's a hot tub out back and a pool out front. It was a very memorable trip that I'll...

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$1,342
avg per night
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