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Florida Rentals with Private Pool

(3573 rentals)
Kissimmee Villa
Sleeps 14, 7 bedrooms, 5 bathrooms
6 reviews

Distance to park: 7 miles to Disney Magic Kingdom

Key Amenities

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

About this property

* Gated and Guarded Resort 7 -10 minutes to Disney * Stunning Lake Views from Enclosed Pool Deck * Pool with 24 Hour Spa on Over ride - Handrails * Lots of Baby Equipment - Free to Use * 2 Lounges - Leather sofas * Game Room Disney Themed -Air conditioned - Slate Bed Pool Table *New Gaming Station...

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Featured review

"Great place to stay"

Our family of 10 rented this property. The host was unbelievable and assisted us every step of the way. The property is clean and neat with everything you could need. Its location is excellent for the parks....

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$270
avg per night
Santa Rosa Beach House
Sleeps 16, 4 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Long to Sea is a 4-story home featuring 4 bedrooms and 6 baths located conveniently near the white sand beaches of Seagrove! It’s just a 4-minute walk to a deeded beach access and includes a 6-seat golf cart to make your journey around 30A a little more adventurous! The home has a private pool and...

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$601
avg per night
Panama City Beach Condo
Sleeps 10, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

***PLEASE USE PROPERTY LINK IN HOST BIO FOR RATES, QUOTES, AND DIRECT BOOKING***.You may use the “contact host” form on this site for other general inquiries.We are private condominium owners and not a management company. We pride ourselves in providing nothing short of a spectacular...

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Featured review

"Great condo"

Great condo with amazing views, comfortable furnishings and a wonderful host!!! We will certainly stay here again.

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$277
avg per night
Port Charlotte House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 4 miles to Port Charlotte Beach Park

Key Amenities

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

About this property

Approx. 1,400 square feet, living room with open kitchen, 3 bedrooms with walk-in closets (1 bedroom with a king-size double bed, 1 bedroom with 2 Twin/XL single beds, 1 bedroom with 2 Twin single beds), 2 bathrooms (thereof one with shower, one with shower & tub combination), 1 kitchen, 1 laundry...

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Featured review

"Vacation comfort"

Our stay at Meehan was very enjoyable. The house met all our needs for the month of our stay. The kitchen was well stocked and there were plenty of towels. All the appliances worked well and each bedroom...

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$130
avg per night
Santa Rosa Beach House
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

Key Amenities

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

About this property

BLISSFUL STAY 30A — PRIME LOCATION. ELEVATED STYLE. NOT YOUR AVERAGE RENTAL. Experience 30A living at Blissful Stay 30A — a designer retreat in Blue Mountain Beach created for families, friends, couples, and unforgettable memories. Sleeps 8.BLISSFUL STAY 30A — PRIME LOCATION. ELEVATED...

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Featured review

"Beautiful home"

I recently had the pleasure of staying at this stunning home in Florida, and I can honestly say it was perfect in every way. From the moment I arrived, I was struck by how beautifully maintained and thoughtfully...

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$616
avg per night

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Indian Shores Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Freshly stocked 3 bedroom, 2 full bath condo located directly on the Gulf of Mexico. Our unit is on the top (5th) floor with views of both the Gulf of Mexico and Intracoastal Waterway. Fully air-conditioned unit sleeps 8 people comfortably. Fully tiled, no carpet!.The unit contains a full size washer...

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Featured review

"Good Family condo"

Great family condo. Owner was very friendly and easy to get a hold of when needed. Great views of both the ocean and intercoastal waterways.

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$363
avg per night
Special Offer
Fort Lauderdale Villa
Sleeps 20, 7 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This majestic Mediterranean-style waterfront villa, nestled in the heart of Fort Lauderdale, is the epitome of the 'Venice of America.' The expansive backyard along a 270-ft dock features a heated pool, outdoor kitchen and bar, a tiki-covered patio, array of lounging areas alongside spaces...

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$3,353
avg per night
Cape Coral Villa
Sleeps 10, 5 bedrooms, 5.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Riverfront home in the Yacht Club area of Cape Coral. New construction 2024. Resort style swimming pool. Dolphin sightings.HIGHLIGHTS:On the river Bright and open indoor and outdoor spaces New construction, modern style, completed in July 2024 Southern rear exposure Gulf access Boat dock...

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Featured review

"Just amazing"

Fantastic brand new and private property right on the river, which leaves nothing to be desired.We have already booked again for next year - top location!

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$783
avg per night
Marco Island House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Magnificent Vacation Home with long water views, pool, and spa with western exposure. Escape to the ultimate waterfront. Getaway on beautiful Marco Island! Discover the serenity of this stunning vacation rental home at the end of a tranquil canal, with fantastic water views from every angle, both inside...

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$539
avg per night
Navarre House
Sleeps 20, 6 bedrooms, 6 bathrooms

Key Amenities

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

About this property

Ultimate luxury on the gulf with your own private balcony pool. A new construction with the state of art kitchen. More windows that you can imagine. View of the water from every room and ceilings that soar to 15 feet. Bring all your family, bring your friends. There is room to sleep 20. Two refrigerators,...

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$894
avg per night
Kissimmee House
Sleeps 6, 4 bedrooms, 3 bathrooms
17 reviews

Key Amenities

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

About this property

Close to the Attractions but away from the crowds. 4 bedroom/3 bath single story home on "lake". Ducks, Sandhill Cranes, sometimes a falcon, turtles. King, king, and 4 twin beds, TV in all bedrooms, WiFi, FREE US, Canada and US Territory phone calls. Fully furnished. Not suitable for...

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Featured review

"Unreal stay"

We had a great week and it was everything they said it was. Stayed in the location before and we will definitely book again.

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$125
avg per night
Marathon House
Sleeps 14, 6 bedrooms, 5 bathrooms
4 reviews

Distance to beach: 0.1 miles to Sombrero Beach

Key Amenities

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

About this property

Waterfront 6 Bedrooms , 5 Baths, canal views. On the HIGHLY sought after Sombrero Beach !!!(We rent weekly only, and our Check-in is on a Saturday and Check-out is on a Saturday dates only so we can optimize our months.)Our houses are safe and clean because we disinfect them with the highest...

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Featured review

"The house was perfect for our fishing trip."

The house was very clean, and location could not be better. The house was more amazing than the pictures showed. The outside tiki hut, (2) barbeque grills and pool made a perfect end to a day of fishing....

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$1,318
avg per night
Largo House
Sleeps 11, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Welcome home! We have put lots of love to make this home the best version of what we would want in a vacation home. The home is completely updated and centrally located to allow you to enjoy multiple beaches during your vacation. It is only a 5 minute drive to Indian rocks beach, 13 min to Clearwater...

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$659
avg per night
Indian Shores Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
12 reviews

Key Amenities

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

About this property

Direct beachfront! Spacious 3 Bedroom 2 bath with fantastic views of the sand and water from your balcony. It's hard to get any closer to the sand and water than from THIS balcony! Panoramic views and gorgeous sunsets. Within walking distance to restaurants, entertainment and shops. Not a high-rise,...

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Featured review

"Sisters Trip"

My 4 sisters, my sister-in-law, and I took this trip together. We had a fantastic time. The condo was perfect, the beach was gorgeous, and we made wonderful memories together. Couldn't have asked for a...

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$480
avg per night
Cape Coral Villa
Sleeps 8, 4 bedrooms, 4 bathrooms
6 reviews

Key Amenities

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

About this property

Experience the fascination of a private luxury villa, with personalized and high end standard. The Villa Sanibel Shell invites you with its luxurious decor, as well as the noble Travertine-floor, to dream, relax and feel at ease. The Villa has an alarm system, individually controlled air-conditioning...

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Featured review

"Great vacation home in Cape Coral"

We spent 5 weeks at Villa Sanibel Shell this year. We have been visiting Cape Coral for the past 9 years. We enjoyed this vacation home the most of any we have stayed at. The home is well stocked especially...

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$325
avg per night
New
Seminole House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Come enjoy this beautiful waterfront home close to Madeira Beach. This home has three bedrooms two baths and a two car garage. Swimming pool and fenced in backyard. Pet friendly home close to shopping and Seminole City Center.

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$439
avg per night
Bonita Springs House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

For DIRECT BOOKINGS, Click to HOST and Visit Website !!!!!Beautiful Décor', Live on the Quiet Pool, Play on the Resort PoolThis Bonita Village Beauty offers 2 Bedrooms, 2 Baths, 2 Pools, 2 Beaches, Chickee and Peloton Equipped Fitness Center!You'll enjoy the look and feel...

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$441
avg per night
Naples Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 6 miles to Marco Island Beach

Key Amenities

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

About this property

Welcome to one of the most desirable locations in all of Naples! Centrally located to Marco Island, Naples Beach, downtown Naples and 5th Avenue. Immaculate, extremely clean, and peaceful - Your paradise vacation awaits at Coral Falls in Lely Resort! Relax from your private top floor balcony with beautiful...

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Featured review

"Family of Three"

This 4th floor condo with an elevator was absolutely amazing. It had everything you could possibly want. The furniture was all new. The condo was immaculately clean. Wonderful view of the pool and hot...

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$288
avg per night
Cape Coral House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Single-story home, step-free access, freshly renovated with new tile flooring throughout (no carpet), all new interior dimmable lights, all new exterior Govee LED Lights (Lanai string lights, Coach Lights, Pool Light), new paint, tons of Florida- inspired decorations and new high quality furniture.Primary...

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$236
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated PoolLocated right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent BeachVILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village...

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Featured review

"Great location!"

The location of this rental was perfect. We were able to walk into the village to shop and eat within a few minutes. Drive time to local attractions was minimal.

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$222
avg per night
Sarasota House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Experience Sarasota's most walkable neighborhood from this stunning 3BR/3BA modern coastal haven with private pool. Discover the perfect blend of luxury and convenience at The Palmetto House. This completely renovated modern coastal cottage puts you in the heart of Arlington Park, Sarasota's...

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$382
avg per night
Cape Coral Villa
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This beautiful vacation villa will enchant you with its special charm.The location is excellent, directly on the canal in the south east of Cape Coral and offers enough space for 6 people. With its heated pool, 3 bedrooms & 2 bathrooms, this villa leaves nothing to be desired. The entire villa...

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$204
avg per night
Special Offer
Naples House
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

We offer short-term and mid-term stays. This listing has amazing month-to-month rates, weekly stays, month-long stays…..Ask us for details!Listing Description of you dream Vacation Your Way vacation home:️ Bedrooms Bedroom 1: King, TV, closet, dresser ️ Bedroom 2: Queen, TV, dresser,...

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Featured review

"This place was such a relaxing and fun place to be!"

This place was such a relaxing and fun place to be. The backyard was definitely the highlight, with the SwimSpa, tiki bar, fire pit, and even an outdoor kitchen, we spent most of our time outside. Inside,...

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$300
avg per night
Panama City Beach Condo
Sleeps 4, 1 bedroom, 1 bathroom
28 reviews

Key Amenities

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

About this property

Enjoy complimentary full beach service with your vacation stay from March 1st to October 31st – a value of over $200 for a one-week stay, included for free!Discover our lovely beachfront condo, perfect for couples, individual explorers, or small families desiring a serene beach getaway with...

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$125
avg per night
Panama City Beach Condo
Sleeps 8, 3 bedrooms, 2.5 bathrooms
56 reviews

Key Amenities

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

About this property

We offer you this beautiful beach front property located at the Shores of Panama. This 23-story gulf front luxury resort is loaded with amenities including a full spa, 13,965 square foot gulf front pool & hot tub, heated indoor pool and hot tub, covered parking on-site, fitness center, 2 tiki bars...

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Featured review

"Shores of Panama Unit 1220"

We stayed 5 days in unit 1220 at Shores of Panama. The property is located in a great area and close to everything we needed. It took us 3 minutes to check in and I never left my vehicle. The condo is very...

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$221
avg per night
Davenport House
Sleeps 26, 9 bedrooms, 5 bathrooms
5 reviews

Distance to park: 12 miles to Disney World

Key Amenities

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

About this property

Family friendly, clean, and spacious in award winning Champions Gate resort. New poolside cinema, 9 bedrooms and plenty of closet space, this villa is absolutely perfect for multi-family groups, sport teams and golf groups. Close to Disney, Wide World of Sports, golf, shopping and dining.Relax in...

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Featured review

"Highly Recommend!"

We brought a large group and stayed for 5 nights at this lovely home. I have been bringing groups to Florida for 18 years and have never found a rental home to be so well cared for, location so perfect...

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$523
avg per night
Cape Coral Villa
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 7 miles to Yacht Club Cape Coral

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Villa Conny, a pleasant south-facing villa on a very large plot with a beautiful view of a small lake. A canoe is also available to explore the lake.Villa Conny was newly renovated and furnished in 2013 and can accommodate six people with two living rooms, three bedrooms and two bathrooms.Let...

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$210
avg per night
Cape Coral House
Sleeps 6, 3 bedrooms, 2.5 bathrooms
1 review

Distance to beach: 18 miles to Fort Myers Beach

Key Amenities

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

About this property

I've designed my home to a mid century modern feel with the goal of making it a cozy home. As a traveler myself, I enjoy meeting new people and renting places that feel like home; I would love to invite you here to share with you my home. This home will come fully furnished. There's a split...

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Featured review

"Perfect mini getaway"

We had a great time at Wendy's place. The communication was super easy and quick. The place is quiet, clean, and spacious -- looks exactly like it does in the pictures. The neighborhood is very conveniently...

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$210
avg per night
Panama City Beach House
Sleeps 16, 5 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Great Location!!! This new 5 Bedroom + Bunk Area has 3.5 Luxurious Bathrooms, Large backyard with Private Pool and pet Friendly! Beach Haven sleeps 14 in beds (Max guests 16)! It has parking for 4 cars. Just steps from the beach! Pool Coming January 1st, 2023. Heated Pool (Pool Heated for additional Fee)....

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$321
avg per night
Key Colony Beach Villa
Sleeps 10, 4 bedrooms, 4 bathrooms
14 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST! IT IS AUTOMATICALLY FIGURED INTO THE QUOTE!The Blue Turtle Villa, located in Key Colony Beach, in the Marathon area, is a gorgeous, brand new, designer decorated canal front duplex with a modern coastal feel! Each side is rented separately and has...

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$737
avg per night
Key Colony Beach Villa
Sleeps 10, 5 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 1 miles to In the Key Colony Beach walking distance

Key Amenities

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

About this property

Hey there, fishing enthusiasts and families!Looking for the perfect Florida Keys getaway? Look no further! My beautiful waterfront home in Key Colony Beach is your dream vacation spot.Imagine this: You wake up to stunning sunrises over the open water, have coffee on the wrap-around porch, and...

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Featured review

"Group Vacation"

Stayed with a group of friends from around the country. The house was very clean and well provisioned Kitchen, bedrooms, bathrooms, outdoor cooking area. Met the host and hostess, who were very pleasant....

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$1,272
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms
13 reviews

Key Amenities

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

About this property

This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the...

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Featured review

"Great Location and Spacious Condo"

We spent a wonderful month in this unit. You can see the beach from the front balcony as it's just across the street. It's very spacious with an open concept living room, kitchen and dining area. It...

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$389
avg per night
Destin House
Sleeps 14, 5 bedrooms, 5.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Sterling Stay!An ideal home for 2-3 families with children- we sleep up to 14 people.Prepare for a one-of-a-kind vacation in this beautiful, modern beach home just steps from the beach! The home is decorated with original artwork, upscale decor and furnishings that create a welcoming...

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$512
avg per night
Cape San Blas House
Sleeps 4, 2 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Seabattical is tucked in a quiet established neighborhood on the gulf side of the North Cape; less than a minute walk to the beach. Oversized parking to accommodate a boat with fresh water hose bibs for rinsing. This is a unique two bedroom, three bath home with a wrap around deck, private inground pool...

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$437
avg per night
Deerfield Beach Apartment
Sleeps 2, 0 bedrooms, 1 bathroom
7 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

You'll love your updated design studio with a king bed where you can run many daily errands by foot, relax by the heated pool, or walk one block to the beach. Take a 9-minute walk to the Deerfield Pier where you'll find a vibrant nightlife, fine dining, shopping, or fish the daily catch! Our...

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$191
avg per night
Miramar Beach House
Sleeps 12, 4 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

LOCATION, LOCATION, LOCATION - Beachside Bliss: Spacious with a cozy feel on an Estate Size Lot - Unique and Rare 4-Bedroom Vacation Home with a PRIVATE SPORTS BOTTOM SWIMMING POOL and FULL SIZE BASKETBALL COURT. Never take a cold shower INSIDE OR OUTSIDE - OUR SUMMERWIND HOMES ARE EQUIPPED WITH A...

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Featured review

"Expectations Exceeded!"

This was the my first time renting a vacation home and the experience at the Summerwind Snowdrift home exceeded my family and I expectations. The owner, Jay, was awesome-easy to work with and answered all...

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$394
avg per night
Fort Myers Townhome
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Beautiful townhouse overlooking 15th fairway/pond at Gateway CC-Hidden Links gated community. 12 ft ceilings surrounded by huge lanai with golf course/water view. Beautifully furnished turnkey….Unit available $5000/mos winter months-minimum 90 day lease

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Featured review

"Tenant's Review"

Sorry to hear that owner does not allow pets due to allergies.Unfortunately no golf or country club access.Very beautiful home with friendly owners neighbors.

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$1,439
avg per night
Kissimmee Villa
Sleeps 14, 6 bedrooms, 3.5 bathrooms
24 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Crush's Crash Pad WDW and M&M Legacy Rentals LLC would Love to welcome your family and friends to our Luxurious 6 bedroom 4-bathroom Oasis at Windsor Hills resort. We are located within the World-Renowned Windsor Hills Resort in Kissimmee, FL, just 2 miles to Walt Disney World. We overlook the...

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Featured review

"Perfect family vacation home"

Great location close to shopping and entertainment. All restaurants within minutes. House is amazing with everything we could have needed. Pool and Hot Tub area perfect for the family and the kids loved...

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$462
avg per night
Miramar Beach House
Sleeps 18, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

WELCOME TO SUMMERHAVEN 4!The ambiance at Summerhaven 4 is definitely laid back and modern amenities as well as cozy comforts provide a wonderful rest at the beach. Since it is right on the water, the views across the jewel toned glistening gulf extend as far as you can see. You are just a few steps...

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Featured review

"Beautiful view right on the beach"

We stayed for a week in September. The location was perfect with great views from the balconies. The place was clean but had a very musty smell. As other reviews mentioned the furniture was very stained....

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$455
avg per night
Panama City Beach Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

This spacious 3BR, 2BA unit sleeps 8 and offers breathtaking Gulf front views the moment you walk in. From the Calypso 17th floor, west tower, enjoy pearl white sands, turquoise waters, and unforgettable sunsets from the full balcony, accessible from both the master bedroom and living room. Perfect for...

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Featured review

"Girls just want to have Fun!"

My friends and I came down for a long weekend girls trip! The condo was the perfect size. We had a wonderful stay here at Calypso 1708! The beds were super comfortable!! The room had everything we needed....

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$185
avg per night
Islamorada House
Sleeps 8, 3 bedrooms, 3.5 bathrooms
31 reviews

Key Amenities

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

About this property

See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe, so you are a block or two from several restaurants and breweries you will fall in love with. The homes are well-apportioned for the discerning traveler.The ONLY pool...

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$1,592
avg per night
Cape Coral Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
7 reviews

Key Amenities

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

About this property

Villa Seashells location, location, location. This beautiful waterfront villa is in Cape Coral situated close to Tarpon point marina and has direct sailboat access to the gulf being only 10 minutes away. This region is so far undiscovered by mass tourism, offers something for everyone. The area is renowned...

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Featured review

"Well maintained home and pool on a canal"

This home is 2 miles from The Boathouse Tiki Bar and Grill and is located in a quiet neighbor hood. The house is well maintained and everyone who stayed with me have a great time.

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$380
avg per night
Islamorada Condo
Sleeps 7, 3 bedrooms, 3 bathrooms
13 reviews

Key Amenities

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

About this property

Oceanfront Islamorada Townhome with Private Dock, Pool & Sunrise ViewsWake up to panoramic ocean sunrises in Islamorada. This 3-bedroom, 3-bath oceanfront luxury townhome features a private dock, sandy entry for kayaks, and a resort-style pool just steps from your door.Your Keys EscapeSet...

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Featured review

"Wonderful place, wonderful people!!!"

The property owners were extremely helpful in every way. If you can't have fun here, you just can't have fun.

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$748
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3.5 bathrooms
11 reviews

Distance to beach: 900 yards to Sombrero Beach

Key Amenities

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

About this property

"BELLA VISTA" - a Spectacular Oceanfront home in Marathon, Fla. with an Invisible-edge heated salt water pool that overlooks the Atlantic Ocean. Open Water Unobstructed VIEWS. VERY PRIVATE. Newly renovated! This 4 bedroom/3.5 bath home can comfortably sleep 8 people. Three bedrooms have King...

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Featured review

"Perfection!"

Don’t think twice about booking this slice of heaven. My family of seven stayed at this glorious home. Absolutely spotless and very well stocked with everything you need. The views are amazing!! 5...

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$1,036
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Casa Feliz~ Experience, enjoy, relax, and rejuvenate in luxury accommodations on the Atlantic Ocean.~ Secluded sophistication can be your vacation destination.Welcome to Casa Feliz! We are located on the quiet Grassy Key in the middle of the Florida Keys.Concierge Level Luxury vacation...

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$1,167
avg per night
New
North Port House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

A canal front outdoor oasis with free heated saltwater pool, kayaks, bikes and fishing poles for your use offering 2 bedrooms and 2 bathrooms in a house with covered lanai and grill, fenced in yard, Canal front. Current availability: March 20, 2026-December 20,2026

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Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
17 reviews

Distance to park: 3 miles to Disney

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Magical Dreams come true in this newly renovated home. Beach and Coastal themed Villa, throughout with something for everyone. We recently renovated the entire home with paint, inside and out, landscaping and decor. Come relax and unwind and enjoy our slice of paradise. The property offers a south...

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Featured review

"Kissimmee Villa (Sept - Oct 2025 = 3 Weeks)"

Overall - perfect location, lovely villa / home, great pool and jacuzzi, everything we wanted and needed! A+A shaky start on arrival with an air conditioning issue, but sorted within a few hours and...

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$140
avg per night
Seacrest Beach House
Sleeps 24, 6 bedrooms, 5 bathrooms
6 reviews

Key Amenities

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

About this property

Seacrest Beach, Florida 6 bedrooms, 6 bathrooms, sleeps 24 Free play arcade games, jacuzzi, large backyard, and pool. Discount grocery shopping servicesNew arcade games, low rates Private pool, jacuzzi, free play arcade game room, large backyard with outdoor TV.Arcade for adults/kids, Jacuzzi,...

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Featured review

"Best Place Ever"

We had a wonderful time with 11 adults and 9 children! The house was very accommodating and had everything we would need. The arcade room was a huge hit with the kids and adults. Some other notable features:...

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$534
avg per night
New
Key Colony Beach House
Sleeps 10, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Weekly rentals in the Keys {and generally elsewhere } are based on a Saturday to Saturday occupancy. Check - in is on Saturday at 4:00 PM, and check - out is on the following Saturday at 9AM . If other times are required \ requested , please inquire. This house is usually not available from the end of...

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Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms
5 reviews

Distance to beach: 1 miles to Sunset Park

Key Amenities

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

About this property

Family-friendly Waterfront Oasis with Private Heated Lazy River Pool and 70' Dock Summary: Welcome to Your Dream Florida Keys Getaway! Bring the family to experience the ultimate Florida Keys vacation! Nestled in family-friendly Marathon—right in the heart of the Keys—our...

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Featured review

"Family vacation."

We could not have asked for a better place to stay. The hosts were absolutely amazing. The lazy river pool was our favorite place to be. The grill ran out of propane one night and we messaged the host and...

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$571
avg per night
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