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Florida Gulf Coast Vacation Rentals

(3600 rentals)
Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 100 yards to Naples beach - mile and miles of public beaches

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Luxury gated beachfront community in Naples, Florida Newly remodeled! 3 Bedrooms - 1 King, 1 Queen, 2 Twin XL 2 bathrooms Full kitchen Washer/DryerWestshore at Naples Cay is the finest of Naples Florida rentals. This end unit condo is in beautiful condition with updated furnishings of top quality....

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Featured review

"Beautiful rental"

This condo had everything and more than you could ask for on a rental. The location to the beach was phenomenal. You had of you were both the bay and the gulf and it had all the beach toys you could ever...

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$741
avg per night
Naples House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to The Cambier Cottage, a charming vacation home nestled in the heart of Olde Naples, Florida. This delightful retreat seamlessly combines comfort, convenience, and artistic flair. Expertly handcrafted by a talented local Naples artist, every corner of this three-bedroom, three-bathroom haven...

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$877
avg per night
Clearwater Apartment
Sleeps 8, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

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

About this property

A one of a kind Luxury Oasis in the heart of Clearwater!Pamper yourself in this spacious and spectacular unit, professionally curated with modern design décor and finishes. Relax and reset by the resort style pool situated in the gated communities multi-million dollar club house. Enjoy all...

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Featured review

"The Cleanest, Most Welcoming Stay with Incredible Hosts"

We had the absolute best time staying at Natasha and Fabio’s Florida property for a weekend getaway! From the moment we arrived, we were blown away by how clean and well-stocked the condo was. It truly...

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$205
avg per night
Bonita Springs House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

A beautiful detached home in a gated golf course community with 24/7 security. Wonderful community filled with welcoming neighbours. Hunters Ridge has a large community pool including tennis courts pickle ball bocce ball walking and bike trails. Workout rooms planned community events and a restaurant...

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Featured review

"Hunters Ridge"

Great location and very nice property. Gated and nice amenities, good location overall for community and this rental. Walking distance to pool and clubhouse.Nice layout, with primary suite separated...

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$167
avg per night
North Port House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

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

About this property

Accommodations: House - 3 Bedrooms - 2 Baths - (Sleeps 6)Beautifully designed private home in North Port, tastefully decorated and furnished, ADT Alarm System, for protection.Our home will make you feel at home the minute you enter through the door. It has everything you need, each bedroom has...

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Featured review

"beautiful home for relaxing and finding great things to do within a short drive"

this home has been very well maintained and the owners style shows in every room the location is wonderful for relaxing while being close to beaches and great shopping the pool is very well cared...

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$226
avg per night

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Gulfport House
Sleeps 6, 2 bedrooms, 1 bathroom
4 reviews

Key Amenities

  • Air conditioning
  • WiFi

About this property

Laidback charm and the simplicity of life at the beach are what you’ll find at Tyn and Marty’s Beach Cottage, located in Gulfport’s Waterfront District. With 2 queen-size bedrooms, 1 bath, a deck overlooking its spacious yard, and an Old Florida vibe that feels like childhood summers,...

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Featured review

"Great cottage, great location, great service!"

Stayed in Tyn & Marty’s Cottage for the first week of May, 2024. The house was very comfortable for the two of us but would easily accommodate more guests. Great outside space to relax in the shade...

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$211
avg per night
Naples Condo
Sleeps 8, 4 bedrooms, 3 bathrooms

Distance to beach: 100 yards to Vanderbilt Beach

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Gorgeous Golden Gate Estates single family home is available for Season, 2024! This spacious new home has 4 bedrooms, den, 3.5 baths, and has stunning upgrades everywhere you look! Start with the curb appeal and lush landscaping, then go inside where you will find a light and bright open floor plan with...

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$467
avg per night
New
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

This well appointed condo on Anna Maria is ready for rent! Everything you need is here for you. Pack some clothes and come to the beach! The condo is fully stocked with pots and pans and virtually any kitchen appliance you will need. We include house towels, beach towels, a washer and dryer and two TV's....

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$285
avg per night
Cape Coral Villa
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Pet friendly
  • WiFi

About this property

Welcome to Villa Emerald, your ultimate retreat in Cape Coral, where sunshine and relaxation meet luxurious amenities. This beautiful Gulf-access home boasts a spacious layout with 3 well-appointed bedrooms and 2 modern bathrooms, ideal for families, friends, or groups looking to escape to a slice of...

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$265
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Sunset Landings Unit 5 is a spacious 2 bedroom/2.5 bath townhome with amazing views of the Gulf of Mexico. With just a few steps across the street, you can enjoy the white sandy beaches and numerous fishing piers. There are no buildings to obstruct your view of the beach!This beautiful townhouse sleeps...

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$281
avg per night
Fort Myers Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy a relaxing stay at Vickie's Hide Away at the South End of Fort Myers Beach. Just a 10 minute walk to the beach or drive to the parking lot and shorten your trip to 5 minutes. Don't want to go to the beach, the heated pool is located at the other end of the building. The Neighborhood consists...

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Featured review

"Our Stay"

Vickie's hideaway If you do not book you are crazy Our stay was great.The condo has everything you need to relax and enjoy the beach and pool. We met so many nice people while staying at the condo. Bill...

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$383
avg per night
St. Petersburg House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Enjoythis fully renovated place in St Petersburg. This house is very close to the beaches, Skyway bridge, St Pete Downtown, Malls. In case you want to have your morning coffee just walking by the water, you are also very close to St. Pete Pier. if you just need to stay home and rest, you can stay at home...

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$120
avg per night
Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

THIS UNIT IS AVAILABLE FOR JAN/FEB/MARCH/APRIL of 2025This beautiful 3 bedroom 2 bath condo is professionally decorated and immaculately kept to perfection. The bedrooms are equipped with a King bed in the master bedroom, and Queen beds in the guest bedrooms. The Great Room features a 60" Television,...

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Featured review

"Dunes"

Wonderful condo. Comfortable, clean, great location. Love everything about this place and the Dunes

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$468
avg per night
Indian Shores Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Private pool
  • WiFi

About this property

ALERT: Beach Cottages Pool and Pool Deck is closed and anticipated to re-open by the end of December. We will have access to a pool 1 block north of us (3 minute walk). This timeline is subject to change without notice.Step into paradise with this beautifully updated ocean view condo at Beach Cottages,...

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$343
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

If you are ready to put your "heels in the sand", look no further. Manna-Tee Beach House is the perfect vacation spot for relaxation on Anna Maria Island. This beautiful 3 bedroom/2.5 bath home located on Holmes Beach on Anna Maria Island has all the amenities for you. Top-of-the-line finishes...

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$380
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 2nd 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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$179
avg per night
Madeira Beach Condo
Sleeps 8, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 2 yards to We are DIRECT OCEANFRONT, 2 steps down to sand!!!

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

These are WEEKLY VACATION RENTALS, if you desire multiple weeks please use weekly pricing schedule, we do NOT do monthly rates. For avail and other questions, best to call us vs email- phone is best as availability changes constantly.Welcome to our warm and welcoming Sea Breeze of Madeira condo...

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Featured review

"Great Vacation Condo"

The condo was spacious, clean, & had an amazing view. Pool was great! Unfortunately, washer & dryer weren’t in the condo but on another floor of the complex. The beach was beautiful & pretty quiet. A...

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$323
avg per night
Special Offer
Sarasota Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 2 miles to Siesta Key

Key Amenities

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

About this property

THERE IS AVAILABILITY FOR JANUARY 2026 DUE TO A CANCELLATION. Stunning 2 bedroom 2 bathroom FIRST floor condo in Ashton Lakes. An assigned carport is steps away from the front door. No worries about climbing any stairs. This beautiful 1356 square foot jewel has a newer kitchen with hardwood cabinets...

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Featured review

"Wonderful location, very clean, landlord thought of everything"

I would highly recommend staying at this condo as it had everything one would need to make their stay enjoyable. The location is wonderful and the condo is on the first floor which helped facilitate carrying...

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$150
avg per night
Marco Island Condo
Sleeps 4, 2 bedrooms, 3 bathrooms

Distance to beach: 1 miles to South Beach

Key Amenities

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

About this property

Escape to Marco Island in this updated 2-bedroom, 3-bathroom townhouse-style bright beautiful renovated condo. Located on the desirable south end, just steps from South Beach, this 1,075 sq. ft. two-story condo is part of Huron Cove, a quiet 10-unit community with a heated pool, boat docks, and canal...

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$316
avg per night
Clearwater House
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to our 2BR/1BA home, only 10-minute drive from Clearwater Beach. Your stay includes access to fantastic shared amenities a refreshing pool to cool off, a cozy fire pit for evening gatherings, a barbecue area for delicious meals, and even mini golf for some friendly competition. It's the ideal...

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$109
avg per night
Anna Maria Island House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Key Amenities

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

About this property

Casa Amiga by Beach Retreats Vacation Rentals 144 Crescent Dr. Anna Maria, FL 34216 City of Anna Maria | 4 Bedrooms | 4.5 Bathrooms | Sleeps 10 | Heated Pool + Jacuzzi | Rooftop Deck | Shared DockLuxury Island Living Near Bean Point Welcome to Casa Amiga, a beautifully designed 4-bedroom, 4.5-bath...

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$896
avg per night
Citrus Springs Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 10 miles to Crystal River

Key Amenities

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

About this property

Simple pleasures, no frills, and affordable – this pristine and uncomplicated space provides everything you need for a comfortable stay. Perfect for snowbirds spending the winter amid the “old Florida” charms of Citrus Springs, and you can bring your doggy! Relax in peace in a quiet...

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Last Minute Deal
Fort Myers Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 25 feet to Fort Myers Beach

Key Amenities

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

About this property

Amenities Update December 2025: The calendar reflects accurate availability. Due to permit delays, the beachfront pool will not reopen until early 2026 and pricing is discounted through January 2026. Beach supplies are provided including a beach buggy, beach chairs, coolers, umbrellas and beach towels....

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Featured review

"Picture Perfect Condo"

Great Condo... Very clean, fully stocked. Looks just like the pictures. Love the location. Very nicely kept grounds. We would come back in a heartbeat. Michelle and the condo management staff are responsive...

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$389
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner

About this property

Views from every window 2 Bedroom/2 Bathroom (no one living above) corner end unit with access to a rooftop deck directly above this sunny and bright unobstructed panoramic view of Sarasota Bay with deeded beach access to one of the most pristine stretches of pearly white Gulf of Mexico sand directly...

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Featured review

"HBC"

Lovely place with a great view of the bay. Well set up with all of the things you need. Owner very accomodating

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$200
avg per night
New
Longboat Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Pet friendly
  • Private pool

About this property

NEW LISTING! Welcome to Bay Dream Believer, your luxurious bayfront escape on beautiful Longboat Key! This bright and beautifully upgraded condo offers breathtaking views of Sarasota Bay through massive picture windows and an enclosed patio that lets you soak in the scenery year-round. Located just across...

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$262
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Please note that surrounding units may still be undergoing improvements. The shuffleboard, club house, and fitness center are currently unavailable until further notice. For updates, please contact SeaBreeze Vacation at .Come relax and enjoy this stunning 2 bedroom/2 bathroom, second level, recently...

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$268
avg per night
New
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Please note that surrounding units may still be undergoing improvements. The shuffleboard, club house, and fitness center are currently unavailable until further notice. For updates, please contact SeaBreeze Vacation at .This cozy and beautifully updated 2-bedroom, 2-bath condo offers a bright, open...

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$269
avg per night
Indian Rocks Beach House
Sleeps 8, 4 bedrooms, 2 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

**Due to damages from Hurricane Helene, 'Mi Casa' is not available for rental. If you have a reservation, please contact Robin Robertson. All records were lost and we have no way of contacting you.**Welcome to 'Mi Casa', our 2 story renovated vacation retreat on Indian Rocks...

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Featured review

"Lovely beach cottage!"

We enjoyed MiCasa for a Thanksgiving celebration with friends. We were all coming from out of state to enjoy the beach. MiCasa is very comfortable and had all the comforts of home. The beds were comfortable,...

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$314
avg per night
Naples Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This spacious condo is the perfect home base for your trip to Naples. Enjoy all the amenities of the Cypress Woods Country Club and a short drive to gorgeous, warm beaches. Naples boasts a lively downtown with lots of shopping, restaurants and beautifully maintained streets for strolls in the evening....

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Featured review

"Comfortable large codo."

This condo is in a gated golf community. We transferred the golf membership and golfed and used their fitness facility. The condo had everything we needed. Two negatives. The noise from highway 75 when...

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$147
avg per night
Naples Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

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

About this property

La Dolce Vita..savour the Naples sweet life in Coral Falls. Newly finished luxury VP flooring in living and bedrooms. Imagine sipping coffee in the morning or wine in the evening on the luxurious lanai with a view of the tranquil preserve. Let it relax you before and after spending time at the pool and...

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Featured review

"Completely met our expectations."

This condo was just perfect for my husband and me. Although it was so close to major roads and shopping amenities, it was very quiet, looking over palm trees, a patio area with covered over picnic tables,...

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$257
avg per night
Gulfport House
Sleeps 7, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 1 miles to Gulfport Beach

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Peach Hideaway is a 3BR/2BA, pet-friendly beauty in Gulfport, featuring a heated swimming pool that’s a big hit with guests.Walk to Gulfport’s beaches, restaurants, pier, and more, then come back to your bug-free pool with a screen enclosure. Nighttime lights and pool heating (76-78...

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Featured review

"Just Peachy"

Perfect for my family of three and two additional guests for a few days. Spacious, well decorated property with everything you need to be comfortable. The pool is immaculate and the outdoor lights makes...

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$273
avg per night
Fort Myers Beach Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 0.0 miles to We have private deeded beach access across street

Key Amenities

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

About this property

Penthouse 2-bedroom/2 baths condo on top 6th floor of low rise on Fort Myers Beach situated along a canal overlooking boats & beautiful sunsets, this property features a king bed in master suite, 1 full bed and 1 twin bed in guest bedroom along with living room queen sofa bed and power recliner for...

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$160
avg per night
Cape Coral House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Villa Surfsidethis gorgeous, modern vacation home is located in the desirable SW area of Cape Coral and features Gulf Access. Villa Surfside is located on a quiet but centrally located street, walking distance to Surfside Shops. Did anyone say Starbucks for breakfast? Not to worry, it...

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$348
avg per night
Naples Condo
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Spacious 3 bdrm/3 bath condo in fabulous Vanderbilt beach location, just a 5 minutes walk from the beach. Watch beautiful sunsets from your lanai on the fourth floor of Regatta. This is a gated community with Resort style amenities, including a beautiful landscaped waterfall pool, a lap pool, a hot tub,...

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Featured review

"Excellent Regatta Rental"

Greatly enjoyed our recent stay at this spacious rental at the Regatta. Perfectly situated within a very short walk to Vanderbilt Beach and an easy drive to restaurants and shops. The unit has just been...

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$489
avg per night
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

This beautiful condo is located in the extremely desirable active Huntington Lakes, which is just minutes from all of the amazing shops, restaurants and the BEACH! This 2-bedroom condo, is fully FURNISHED and stocked with everything that is needed. It is a gated community with plenty of activities such...

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$117
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

Discover island paradise at “Magnolia” located on Magnolia Ave., a *premier residential street* just south of Pine Ave. in Anna Maria. Magnolia is just 2 blocks from the gorgeous, white sandy beaches of Anna Maria Island, 1 ½ blocks from the charming Ginny & Jane E’s Café,...

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$609
avg per night
New
Cape Coral House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to The Villa Enterprise! Our stunning location right on Memory Lake is the perfect spot for a relaxing getaway. With an electric heated pool and spa, as well as a large patio for entertaining or simply soaking up the sunshine, you'll never want to leave. The electric fireplace, equipped for...

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$211
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 800 feet to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Brand New Condo, completely renovated. 2 Bedroom, 2 Bath large condo with granite kitchen and baths. Tile deck flooring. Full water views from our 6th floor location. See all the way to end of Anna Marie on clear day. Ringling bridge, downtown Sarasota, Lido and Bird Key views. King bed in master...

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$183
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to "Beach Escape" on beautiful Anna Maria Island. Appropriately named, this Mediterranean-inspired beach house offers all the charm and luxury you expect from a memorable vacation on AMI.Find ease and relaxation the moment you arrive, this charming multi-level home is nestled among...

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Featured review

"Escape to Paradise"

Everything was Perfect. The only thing I would change is to Stay Longer! Everything was wonderful. Location was perfect, the Beach, the Pool and the Restaurants.

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$495
avg per night
Cape Coral House
Sleeps 6, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

Just pack your clothes, sit back and enjoy your vacation in this 3 bedroom 3 bathroom home plus den located on a fresh water canal. This beautiful villa is located in a quiet residential neighborhood and features a grand open floor plan with sliding glass doors which open to the spacious lanai and electrically...

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Featured review

"Cape Coral"

This house was a wonderful place to vacation. Lots of room, beautiful view. I would recommend it to anyone.

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$200
avg per night
Babcock Ranch Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • WiFi

About this property

Welcome To Babcock National Golf & Country Club ~ Welcome to Paradise! Rent 3 Months During Season 2026 and get month of APRIL FOR FREE !!! (Book Jan, Feb & March 2026, Receive Month of April at no additional charge)This 1st Floor Terrace Condo offers guests 2 Bedrooms & 2 Bathrooms,...

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$160
avg per night
Largo House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 5 miles to Indian Rocks Beach

Key Amenities

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

About this property

If there's a place that captures the essence of relaxation, it's our bright, spa-like oasis. Just minutes from the beach, with a sparkling clean hot tub, and a huge backyard with a smokeless firepit, our home has everything you need to have a relaxing getaway. The interior is bright with lush...

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$165
avg per night
Anna Maria Island Apartment
Sleeps 4, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to “Barefoot Mermaid 1” 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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$339
avg per night
Indian Shores Condo
Sleeps 4, 1 bedroom, 1 bathroom
16 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Fabulous Beach Condo! DIRECT WATERFRONT!! Enjoy our Newly Renovated 1 bedroom, 1 bathroom fully appointed kitchen. Located RIGHT ON the intra coastal and across the street from the Beautiful Gulf of Mexico!! 1st Floor and out the door to relax on the private patio and watch the boats go by and catch...

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Featured review

"Sand castle 2"

Recently stayed at the Sand Castle 2 condominiums. It was a great stay. Right across the street from Caddy’s at Indian Shores and a short drive to anything you were hoping to do while you were in Florida...

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$221
avg per night
Punta Gorda Villa
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Just steps away from the largest deep-water Marina in southwest Florida, the Fitness, Racquet & Pool Club and an on-site waterfront restaurant, our Seabrook in the South Villa, located in the Resort at Burnt Store Marina, is where you have your chance to enjoy the Florida lifestyle that everyone dreams...

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$127
avg per night
Naples House
Sleeps 12, 6 bedrooms, 7.5 bathrooms

Key Amenities

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

About this property

This home is truly what living in Olde Naples is all about! A spacious home great for entertaining, enjoy the outdoors on the verandah or out by the pool, walk to the beach, and easily enjoy Fifth Ave and Third street shopping, dining and entertainment! Open & bright, loaded w/upgrades! Absolutely...

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$1,975
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Amazing views from the living room and primary bedroom of this 2 bedroom/2.5 bathroom. Take a drink outside and sit on your private balcony and watch the incredible sunsets. This beautiful condo sits right on the beach in Holmes Beach. After a day on the beach, take a dip in the community pool or sit...

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$500
avg per night
Indian Shores Condo
Sleeps 4, 1 bedroom, 1 bathroom
57 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Settle into waterfront living at Barefoot Beach Resort, a ground-floor condo with a rare private patio directly on the Intracoastal. Enjoy coffee, cocktails, and dolphin watching right from your own outdoor space.This 750 sq. ft. unit includes a full kitchen, pool access just steps away, and private...

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Featured review

"Beautiful view bay front condo"

This was a beautifully decorated condo with beautiful views of the bay. Everything we needed was provided, such as beach supplies, towels, kitchen was fully stocked with everything you need. The condo...

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$204
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Create unforgettable memories at “Crescent Palms”. This *perfect island house* has been fully renovated in 2025. Crescent Palms is centrally located, just north of Pine Avenue in Anna Maria. This home is steps away from the gorgeous white sandy beaches of Bayfront Park, having captivating...

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Featured review

"Peaceful and relaxing family trip"

We were looking for a quiet spot for the family and hit the bullseye at Max and Denise's place on Northern Anna Maria island. Centrally located, 3 blocks either way, between the Gulf of Mexico or Tampa...

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$580
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
15 reviews

Key Amenities

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

About this property

Roomy 2 bedroom, 2 full bath condo in prime Siesta Key location. Comfortably furnished living room, dining area, all linens and fully equipped kitchen included, ceiling fans in all rooms, Flat screen tv in living room with DVD player and a flat screen in the master bedroom. Master bedroom has queen-size...

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Featured review

"Comfortable unit"

The property was nice and comfortable. The children enjoyed the pool that was close to the unit. Owner promptly responds if we had questions.

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$272
avg per night
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FAQ

Location & Region Specifics

What are the main regions of the Florida Gulf Coast (e.g., Emerald Coast, Suncoast, Nature Coast)?

The main regions of the Florida Gulf Coast include the Emerald, Forgotten, Nature, Sun, Cultural, Lee Island, and Paradise Coasts.

Which Gulf Coast towns are best known for their beautiful beaches?

Venice, Fort Myers, Boca Grande, Destin, and South Walton, Florida, all have beautiful beaches.

What is the difference in atmosphere between the Panhandle (e.g., Destin, Panama City Beach) and the Lower Gulf Coast (e.g., Naples, Marco Island)?

The atmosphere in Panhandle cities tends to be lively and bustling, while in the Lower Gulf Coast cities, the atmosphere is more relaxed and casual.

Which Gulf Coast destinations are less crowded and more laid-back?

Bonita Beach, Sanibel Island, Apalachicola, and Madeira Beach are just a few areas that offer a quiet, laid-back atmosphere.

Activities & Vibe

What part of the Gulf Coast is best for families with young children?

The Sun Coast (Clearwater, St. Petersburg), the Lee Island Coast (Ft. Myers), and the Cultural Coast (Sarasota) are some of the best areas for families with young kids.

Where can I find the best shelling beaches on the Gulf Coast?

Clearwater Beach, Indian Rocks Beach, St. Pete Beach, and Treasure Island are all great spots for shelling.

Which Gulf Coast towns have the most vibrant nightlife and dining scenes?

Destin, St. Petersburg, Siesta Key Beach, and Panama City Beach all have lively nightlife and lots of restaurant options.

What are the top attractions and things to do along the Gulf Coast, besides the beach?

Some top attractions include the Dolphin and Manatee Adventure Tour in Ft. Myers, the Bird Gardens of Naples, airboat tours through the Everglades, and Weeki Wachee Springs State Park in Spring Hill.

Cost & Affordability

Which towns or cities on the Gulf Coast offer the most budget-friendly rental options?

Ft. Myers, Clearwater, St. Petersburg, Pensacola, and Sarasota all have budget-friendly options for renters.

When is the "shoulder season" or off-season for the Gulf Coast to find the best deals?

The Gulf Coast’s off-season stretches from September to November. Many owners lower their rates because rentals are in less demand. The shoulder season happens in between off- and peak season, which runs from December to April.

Are rentals typically cheaper if they are a short walk or drive from the beach versus directly on it?

Rentals that are a short distance from the beach are usually more affordable than rentals sitting directly on the sand.

What are some tips for finding affordable rentals during peak season?

One tip is to start looking for a rental early so you can reserve it several months ahead of time. Also, booking the rental for longer than a few days or one week may get you a deal on the rate.

Finding Rentals

How can I filter my search for rentals that fit a specific budget?

Enter your preferred range of rates into the search filter to narrow your results.

Are there hidden costs I should be aware of, like resort fees or parking fees?

Some potential fees include those for cleaning, damage protection, pets, etc. Carefully read the listing’s description to learn about any fees.

Is it generally cheaper to rent directly from an owner versus a property management company?

Yes, as a general rule, it’s less expensive to rent from an owner than a property management company.

What types of rentals (e.g., small condos, duplexes) are usually the most affordable?

Small condos and cottages are budget-friendly choices for renters visiting Florida’s Gulf Coast.

Property Type

What are the typical amenities included in a Gulf Coast condo rental (e.g., pool, gym, beach access)?

The typical amenities of a condo for rent on the Florida Gulf Coast include air-conditioning, a fitness room, towels, a pool, Wi-Fi, kitchen appliances, parking, a patio or deck, and beach chairs.

What is the difference between a high-rise and a low-rise condo complex, and what are the pros and cons of each?

A high-rise condo complex has ten or more stories, while a low-rise has no more than nine stories. A low-rise condo has more units on each floor. A high-rise condo has better views than a low-rise, and people on the higher floors have a quieter atmosphere. While a low-rise is more affordable, it may only have stairs and not an elevator like a high-rise.

Are condo rentals better for smaller groups and couples than full-size houses?

Renting a condo makes more sense for smaller groups and couples. A full-size house would be more expensive and likely have more space than you need.

What should I know about condo association rules before booking?

The owner of the property is likely to brief you on the condo association’s rules. An owner is responsible for any damage or issues that arise if a renter breaks a rule.

Booking & Logistics

Do most condo rentals include dedicated parking spots?

Most condo owners make parking available to renters. It may be a dedicated spot or an assigned carport where you can park. Check with the property owner for specifics on parking.

How do I find out about the specific location of a condo unit (e.g., floor number, view direction)?

A condo’s description may include the floor number and information about the view. If not, message the owner with specific questions.

Are things like beach chairs and umbrellas typically provided by the condo owner or the complex?

Beach chairs, umbrellas, and towels are typical amenities listed in an owner’s description of a condo.

Is it common for condos to have on-site management for check-in and assistance?

Yes, many condos have on-site property management for check-in and to address any issues a renter may have.