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Summerland Key Rentals with Pools

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41 Houses in Summerland Key with pools

Blue vacation home, water front, boat dock, heated private Pool.

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$556

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$332

Family Friendly House In Paradise

Summerland Key house

5 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$516

Acreage Multi-Million Dollar Beachfront Mansion w/ Pool & Billiards

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$1,718

The Helms House

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$285

KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Your Boat & Ai

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 3 hours 50 minutes

Match: Swimming pool

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Price per night from

$178

New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 50 minutes

Match: Swimming pool

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Price per night from

$295

New Listing!!! ANCHORS AWEIGH- Charming Oceanfront Home, Perfect for Multiple Fa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 3 hours 50 minutes

Match: Swimming pool

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Price per night from

$178

Reel Paradise

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$284

Great rentals within 20 miles that match your search

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

4 bedrooms / 3 bathrooms / sleeps 11

Match: Swimming pool

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Price per night from

$893

The Conchy Tonk

Stock Island townhouse

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$200

Blackbeard's Escape

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$357

Cassie's Paradise

Sugarloaf Key house

5 bedrooms / 4 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$5,698

BLUE DOLPHIN - Waterfront Home, Dock Your Boat, Community Pool/Hot Tub, Tennis C

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 50 minutes

Match: Swimming pool

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Price per night from

$178

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 20

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 3 hours 9 minutes

Match: Swimming pool

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Price per night from

$2,199

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

Match: Swimming pool

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Price per night from

$573

Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE

Key West apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

Match: Swimming pool

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Price per night from

$315

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 14

Match: Swimming pool

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Price per night from

$687

Fandango

Cudjoe Key house

5 bedrooms / 3 bathrooms / sleeps 14

Match: Swimming pool

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Price per night from

$687

Ocean View Estate with Private Pool 15 minutes from Key West

Key West house

4 bedrooms / 2 bathrooms / sleeps 10

“Absolutely Perfect for Our Family of 11” We couldn't have asked for a better place for our family. Everyone had a comfortable bed, we had everything we needed for cooking, and there was plenty for everyone to do. If we needed something, we could find it easily, or we called Cynthia---her help and knowledge is priceless! Kris stopped in twice to check on us, and we found him delightful. He knows so much history about the area! There is a large pool and a large play area with anything and everything you can imagine to play with, Since we had very young children with us, we were very happy with the lack of ocean access, as well as the locking gates to the pool area and the outside stairs. When we come back to the Keys, we will definitely stay at the White Ibis Inn!

Responds fast! avg. 2 hours 59 minutes

Match: Swimming pool

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Price per night from

$544

Coral Palm 3 bedroom, 3 bathroom townhome at Coral Hammock, Pet Friendly!

Stock Island townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$166

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$343

Blue Palms Retreat. ocean front w/pool and dock for your boat.

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$573

5 Pirate's Hideaway Canal Front Home with Seawall & Kayaks

Little Torch Key house

3 bedrooms / 3 bathrooms / sleeps 7

Match: Swimming pool

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Price per night from

$247

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 3 bathrooms / sleeps 7

Match: Swimming pool

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Price per night from

$1,946

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

8 bedrooms / 5 bathrooms / sleeps 20

Match: Swimming pool

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Price per night from

$747

Yellow vacation home, water view, boat dock, heated private pool.

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$476

Amazing 3 bedroom poolside house minutes to Key West. Great prices

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$716

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 41 minutes

Match: Swimming pool

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Price per night from

$252

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$258

TROPICAL TREASURES - Beautiful Canal Front Home On Cudjoe Key With Quick Open Wa

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 50 minutes

Match: Swimming pool

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Price per night from

$144

PARADISE POINT - Amazing Views, Luxurious Open Water Home W/ Pool, Tiki, Dockage

Sugarloaf house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 50 minutes

Match: Swimming pool

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Price per night from

$458

Coral Breeze Monthly Vacation Rental by AT HOME IN KEY WEST

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$130

Cottage by the Pool Monthly Vacation Rental by At Home in Key West

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$127

Wind Swept Monthly Vacation Rental in The Key West Golf Club

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 6

Match: Swimming pool

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Price per night from

$130

Coral Villa Monthly Rental by AT HOME IN KEY WEST

Stock Island townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$166

Bye Bye Birdie Monthly Vacation Rental by At Home in Key West

Stock Island townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$159

A Little Slice of Paradise Monthly Vacation Rental by AT HOME IN KEY WEST

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 5

Match: Swimming pool

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Price per night from

$127

Viewing 38 of 41
rentals in Summerland Key

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