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Featured Condo Rentals in Summerland Key and around

Our top choices for Summerland Key condo rentals

CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!

9.8 out of 10, Exceptional, (154)
"Great place"
The price is €216
includes taxes & fees
26 Aug - 27 Aug
CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!

Parking, Pool, & Pet Friendly - The Grenada Suite

8.6 out of 10, Excellent, (11)
"The room was ad adverted, clean, quiet property, will stay again."
Parking, Pool, & Pet Friendly - The Grenada Suite

Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK

8.8 out of 10, Excellent, (117)
"Clean comfortable and plenty of room. "
The price is €269
includes taxes & fees
8 Sept - 9 Sept
Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK

Comfortable Condo with Pool, Private Balcony, & Beach Access

8.6 out of 10, Excellent, (134)
"Nice area, location, and wonderful apartment!"
Comfortable Condo with Pool, Private Balcony, & Beach Access

Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

8.8 out of 10, Excellent, (200)
"Perfect for our 3 nights in Key West"
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

Dog-Friendly Sunrise Suites Condo with Pool, Hot Tub & Free Parking

9.2 out of 10, Wonderful, (156)
"Close to Smathers Beach and just a short drive to Duval Street!"
Dog-Friendly Sunrise Suites Condo with Pool, Hot Tub & Free Parking

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

9.8 out of 10, Exceptional, (34)
"Great property, easy access to everything. Definitely will make this a return spot!"
Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Tropical Getaway with Private Balcony, Shared Pool & Hot Tub - Dogs OK

9.0 out of 10, Wonderful, (120)
"Very nice place to stay. We really enjoyed our visit. Would recommend for anyone visiting Key West. "
The price is €272
includes taxes & fees
26 Aug - 27 Aug
Tropical Getaway with Private Balcony, Shared Pool & Hot Tub - Dogs OK

WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

9.4 out of 10, Exceptional, (11)
"Great time staying there "
The price is €199
includes taxes & fees
27 Aug - 28 Aug
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

Pool View 3BR Residence | Beachside Resort

9.0 out of 10, Wonderful, (2)
"I had the pleasure of bringing my family down to the keys for their visit. The place was beautifully located and the view is picturesque. The condo itself was easy to check into & truly beautiful. Vaulted ceilings, spacious sleeping quarters and large tub made the stay an exquisite experience. I very much look forward to a future visit & highly recommend."
Pool View 3BR Residence | Beachside Resort

Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis

9.0 out of 10, Wonderful, (102)
"Very clean and beds are so comfortable. "
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

9.4 out of 10, Exceptional, (90)
"We really enjoyed the property. "
The price is €222
includes taxes & fees
26 Aug - 27 Aug
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Dog-Friendly Retreat with Pool, Hot Tub, Tennis - Balcony with Pool Views

7.8 out of 10, Good, (85)
"Family friendly , clean and nice location."
Dog-Friendly Retreat with Pool, Hot Tub, Tennis - Balcony with Pool Views

Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!

8.4 out of 10, Very good, (25)
"Property as described in listing, enjoyed our stay! Would def stay again! "
The price is €209
includes taxes & fees
26 Aug - 27 Aug
Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!

COCONUT PALM STUDIO ~ Adult Only Studio, Heated Shared Pool & Close to Town!

9.6 out of 10, Exceptional, (90)
"Great stay, clean property in a perfect location that is quiet and still walkable. Would gladly stay here again!"
The price is €233
includes taxes & fees
1 Sept - 2 Sept
COCONUT PALM STUDIO ~ Adult Only Studio, Heated Shared Pool & Close to Town!

Old Town "Eleuthera" • 2BR Waterfront Corner Condo

10.0 out of 10, Exceptional, (24)
"Perfect accommodations and location for our girls trip weekend! We were able to walk to all the spots and had a blast! "
Old Town "Eleuthera" • 2BR Waterfront Corner Condo

GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!

9.8 out of 10, Exceptional, (89)
"We loved the place; the secluded pool between the vegetation, the room and little extras made this stay above our expectations!"
The price is €260
includes taxes & fees
26 Aug - 27 Aug
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!

NumberEleven ~ Charming Adult Only, 1 Bedroom, 1 Bath w/ Shared Pool!

9.8 out of 10, Exceptional, (75)
"Great location. "
NumberEleven ~ Charming Adult Only, 1 Bedroom, 1 Bath w/ Shared Pool!

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

8.6 out of 10, Excellent, (138)
"I love this place friendly and quiet.Close to the town.Farmacy,CVS,Denny’s Rest."
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Private Parking & Waterfront - Grand Marina Suite

9.4 out of 10, Exceptional, (9)
"We selected this condo for its location, cost and amenities; all met or exceeded our expectations. Super nice, clean and quiet. We'll be back!"
Private Parking & Waterfront - Grand Marina Suite
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Summerland Key Hotel Reviews

Frequently asked questions

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What is there to do in Summerland Key near my condo?
The ultimate travel accessory is a well-planned itinerary. Florida Keys Beaches is a wonderful place to begin your sightseeing in Summerland Key.