COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Florida Keys Rentals with Pools

Updating...

age 0-16
850 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

850 house rentals in Florida Keys with pools

75731 Overseas Highway

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

“Vacation of a lifetime!” I can't say enough good things about this home. It was beautiful, clean, and peaceful. The only thing that might be considered a down side is that all of the bedrooms are located upstairs, but that was not a problem for us. Brandi at Freewheeler Realestate was wonderful. She was prompt with answers to questions, friendly and professional. The home-owner obviously wants to see to it that the people staying in their home are well taken care of. Everything was great all the way down to the fluffy beach towels. We will definitely look at staying at this home again.

Match: Swimming pool

All filters match

Price per night from

$1,227

Amazing Ocean View Condo on the Beach!

Marathon apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Our Spirits were renewed!” Things don't happen by chance! Little did we know six months ago when we booked our vacation how much we would really, really NEED a quiet and peaceful week! This little corner of Marathon is exactly that: quiet and peaceful. The condo is very comfortably furnished, very clean, and the view is - well, I don't think there is a 'better' view anywhere! It's picture perfect - even to the gorgeous green iguana on the palm tree! (but you have to look quick - they move fast!). We had our son, daughter in law and two little grandkids with us...it was perfect! Sunrise with coffee by the pool, under the Chickee or on the patio...awesome! Lots to do for families or singles very close by...yup...you really can even have pizza delivered if you don't want delicious, fresh seafood!..and wow! are there some awesome spots for that!! Communication with the owners is impeccable...could NOT be better. These are the folks with whom you love to do business!! Thanks so much, Todd and Jamie!

Responds fast! avg. 2 hours 22 minutes

Match: Swimming pool

All filters match

Price per night from

$236

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / sleeps 6

“awesome” The unit was great, the views of the sunrise were amazing. Enjoyed our stay! The owner Deanna L unit 303 .

Match: Swimming pool

All filters match

Price per night from

$224

Spectacular Atlantic Ocean View Condo (MONTHLY)

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranquil. The patio faces south so you don't get blasted with the morning or evening sun making it very comfortable having your morning coffee or evening cocktail while enjoying the view. The owners have put a lot of thought into furnishing and accessorizing the unit. Tess and Mimi were wonderful to work with (Mimi met us at the condo and had great advice on where to eat, what to do...)I have stayed in several condos and this was by far my favorite, if your thinking of staying here you will not be disappointed. I will definitely be back the next time I visit the keys.

Match: Swimming pool

All filters match

Price per night from

$334

Oceanfront condo w/beach access, shared tennis, pool, etc. - marina available!

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

All filters match

Price per night from

$147

ADVENTURE AWAITS I - MARINER'S CLUB 606 - KEY LARGO RESORT STYLE VACATION HOME

Key Largo townhouse

4 bedrooms / 4 bathrooms / sleeps 10

Match: Swimming pool

All filters match

Price per night from

$458

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

2 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

All filters match

Price per night from

$572

Bayside 3BR/3BA w/ Heated Pool, Dock Access, Rooftop Terrace & Stunning View

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

All filters match

Price per night from

$142

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 8 w/ 60 Feet of Dockage

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 59 minutes

Match: Swimming pool

All filters match

Price per night from

$261

SPECIAL FALL RATES, INCL. LABOR DAY - BOOK NOW!

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

All filters match

Price per night from

$287

Large Townhouse in Mariner's Club Resort - 3 BR/3.5 Bath

Tavernier townhouse

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 37 minutes

Match: Swimming pool

All filters match

Price per night from

$338

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 49 minutes

Match: Swimming pool

All filters match

Price per night from

$203

Tropical Escape

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Very comfortable and all around great place to stay.” It was very clean, comfortable and homey. The pool was great and it's very close to Key West and a beach. We really enjoyed our stay. Provided plenty of towels, pool accessories, kitchenware, etc.... No complaints.

Match: Swimming pool

All filters match

Price per night from

$249

Canal-Front 3BR w/ Private Pool, Boat Slip, Tiki Hut & Kayaks - Near Beach

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

All filters match

Price per night from

$227

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 1 hour 21 minutes

Match: Swimming pool

All filters match

Price per night from

$232

Top floor, two bedroom,two bath condo with private balcony,close to the Ocean

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 47 minutes

Match: Swimming pool

All filters match

Price per night from

$346

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

All filters match

Price per night from

$1,718

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 12 minutes

Match: Swimming pool

All filters match

Price per night from

$318

New 3 bedroom luxury condos just 10 mins from 10 beaches!!

Dry Tortugas National Park apartment

3 bedrooms / 3 bathrooms / sleeps 5

Match: Swimming pool

All filters match

Price per night from

$115

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 38 minutes

Match: Swimming pool

All filters match

Price per night from

$166

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 0 minutes

Match: Swimming pool

All filters match

Price per night from

$654

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect place to experience Key West” This is a lovely condo with a tropical, quiet view. Many extras are included: beach towels, bikes, and kitchen supplies. The pool area was our favorite spot, and we had coffee every morning on the balcony with chairs for all 6 of us. My husband enjoyed watching March Madness on the large T.V. Kathy did a fantastic job with all communications and provided great tourist tips. We would definitely stay here again!

Responds fast! avg. 2 hours 29 minutes

Match: Swimming pool

All filters match

Price per night from

$430

Oceanfront Condo - Pool, Beach, Tennis & Marina

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 44 minutes

Match: Swimming pool

All filters match

Price per night from

$229

OUTSTANDING Oceanfront House with Pool and Deep water dockage!!

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

“Marathon house” A great house with an awesome ocean view! The house was very clean and the kitchen was well stocked with all we needed. We especially looked the pool area and boat dock. It accommodated our 38 ft fishing boat we brought with no problems. I would highly recommend this rental

Responds fast! avg. 2 hours 22 minutes

Match: Swimming pool

All filters match

Price per night from

$654

Key Largo Kampground Vacation

Key Largo house

1 bedroom / 1 bathroom / sleeps 3

“Great location and pleasantly surprised!” Romberto's Camprground vacation was definitely more than i expected. There was ample room for my husband and I, the folks were nice and the area was quiet and clean. The marina was convenient (small boats only). There was a small leak in the bathroom in the overhead skylight but it was almost negligible unless it was pouring. we will definitely be back.

Responds fast! avg. 3 hours 15 minutes

Match: Swimming pool

All filters match

Price per night from

$145

Key Colony Beach Home

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

All filters match

Price per night from

$207

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

Match: Swimming pool

All filters match

Price per night from

$430

Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

“Nice alternatif for hotel” We were on the boat with only 2 people, so plenty of place ! We liked the marina and the boat very well. Something completely different than an hotelroom ... We had perfect weather so we used the different terraces on the boat depending on the wind and sun. The only point what could be better is the quality of the bedding (sheets, blankets, towels...) For this price you expect some better quality. Anyway, when we wil go back to the us I certainly will search for something similar to stay on

Match: Swimming pool

All filters match

Price per night from

$165

Bay Harbour D-114

Long Key house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

All filters match

Price per night from

$328

Key West Florida Beachfront Condo

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

“Better than the photos” Condo is perfectly located at the beach. Well designed for easy living both inside and out. Great advise on where to visit and eat thanks

Match: Swimming pool

All filters match

Price per night from

$403

Incredible Luxury Home with Waterfront!! Paradise

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 39 minutes

Match: Swimming pool

All filters match

Price per night from

$1,404

Dream Escape in Islamorada at Anglers Reef

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 8 minutes

Match: Swimming pool

All filters match

Price per night from

$347

Southard Square Hideaway

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Match: Swimming pool

All filters match

Price per night from

$120

Key Largo 2/2 Tropical Daze Oceanfront Condo

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Couldn't be better!!!” If you are looking to rest and relax, look no further.

Responds fast! avg. 2 hours 16 minutes

Match: Swimming pool

All filters match

Price per night from

$228

Ocean pointe island retreat

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 28 minutes

Match: Swimming pool

All filters match

Price per night from

$226

Indigo Reef, 32' dock, Marathon FL

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

All filters match

Price per night from

$347

NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 16 minutes

Match: Swimming pool

All filters match

Price per night from

$172

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

All filters match

Price per night from

$347

Viewing 38 of 850
rentals in Florida Keys

×

Also consider