Vacation Rentals with Pool in Islamorada

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Filtering by: Swimming pool

265 vacation rentals

(15) Excellent 

21

Islamorada Luxury Waterfront Condo with Boat Slip

Florida Keys / Islamorada

Islamorada apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Beautifully appointed, waterside condo!” This property is a beautiful, two bedroom condo, very well appointed, with everything we needed for a great stay! Islamorada is a great middle point to see the other parts of the Keys, and close to great restau
…see more

Price per night from

$214

Price per night from

$214

(2) Excellent 

21

Ocean-Front Caribbean Home.

Florida Keys / Islamorada

Islamorada house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$1,500

Price per night from

$1,500

(3) Excellent 

9

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

Florida Keys / Islamorada

Islamorada apartment

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$175

Responds fast!
avg. 29 minutes

Price per night from

$175

(4) Excellent 

16

Newly refinished condo open water views very nice

Florida Keys / Islamorada

Islamorada condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$200

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$200

40

SPACIOUS 2 BEDROOM TROPICAL OASIS WITH FLORIDA BAY SUNSET VIEWS!

Florida Keys / Islamorada

Islamorada condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$171

Price per night from

$171

(3) Excellent 

21

BEACON REEF 310

Florida Keys / Islamorada

Islamorada apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$110

Price per night from

$110

65

100 Palo De Oro Drive

Florida Keys / Islamorada

Islamorada house

4 8 28 nights min

  • 4 bedrooms
  • sleeps 8
  • 28 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$422

Price per night from

$422

(3) Excellent 

33

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

Florida Keys / Islamorada

Islamorada condo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$110

Responds fast!
avg. 2 hours 58 minutes

Price per night from

$110

25

Anglers Reef Islamorada Florida Sleeps 6

Florida Keys / Islamorada

Islamorada house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$300

Price per night from

$300

22

Dream Escape in Islamorada at Anglers Reef

Florida Keys / Islamorada

Islamorada villa

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$250

Responds fast!
avg. 2 hours 24 minutes

Price per night from

$250

(2) Excellent 

25

MATECUMBE JEWEL

Florida Keys / Islamorada

Islamorada house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet Friendly
“Our Lobster Trip to the Keys” My family and I stayed at the Matecumbe Jewel in the month of august for Lobster season. The home shows even better than the photos, was clean, well furnished and kept. We could not have asked for better accomodations wh
…see more

Price per night from

$157

Price per night from

$157

(2) Excellent 

25

PALMS 309

Florida Keys / Islamorada

Islamorada house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$85

Price per night from

$85

(5) Excellent 

31

FLORIDA KEYS OASIS # The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****

Florida Keys / Islamorada

Islamorada house

5 12 4 nights min

  • 5 bedrooms
  • sleeps 12
  • 4 nights min
  • Nearest beach 4 mi
  • Swimming pool
  • Child Friendly
“Relax in Luxury” Great Location. Lots of nearby restaurants. Owners were extremely helpful in recommending attractions. A stunningly beautiful home with plenty of room for my large family to spread out. Pool was great. Swimming in warm shallow wa
…see more

Price per night from

$1,248

Responds fast!
avg. 1 hour 17 minutes

Price per night from

$1,248

(7) Very Good 

Certificate of Excellence

14

Oceanfront 2 Bedroom/2 Bathroom Well Maintained Condo with Large Balcony

Florida Keys / Islamorada

Islamorada condo

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Certificate of Excellence

Price per night from

$135

Price per night from

$135

(7) Excellent 

18

No dockage allowed. Florida Keys. Beautiful condo. Short walk to the beach area.

Florida Keys / Islamorada

Islamorada villa

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$249

Responds fast!
avg. 1 hour 36 minutes

Price per night from

$249

56

Islamorada Oceanfront Estate, Pool, Beach Cottages-- Sea Ranch -- Florida Keys

Florida Keys / Islamorada

Islamorada house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,178

Price per night from

$1,178

(28) Excellent 

38

Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental

Florida Keys / Islamorada

Islamorada house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated
…see more

Price per night from

$457

Responds fast!
avg. 1 hour 25 minutes

Price per night from

$457

33

152 Valencia Drive

Florida Keys / Islamorada

Islamorada house

4 8 28 nights min

  • 4 bedrooms
  • sleeps 8
  • 28 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$263

Price per night from

$263

(1) Excellent 

24

LYONS LANDING

Florida Keys / Islamorada

Islamorada house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet Friendly

Price per night from

$245

Price per night from

$245

(5) Excellent 

19

THIS IS IT! Magnificent Oceanfront Paradise! WE ARE OPEN!!

Florida Keys / Islamorada

Islamorada condo

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$142

Responds fast!
avg. 3 hours 4 minutes

Price per night from

$142

(6) Excellent 

20

Luxury condo overlooking harbor with ocean view

Florida Keys / Islamorada

Islamorada condo

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$269

Responds fast!
avg. 1 hour 7 minutes

Price per night from

$269

27

Ultra-Luxurious Oceanfront Estate on Millionaires’ Row

Florida Keys / Islamorada

Islamorada villa

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$1,571

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$1,571

(1) Excellent 

24

PALMS 214

Florida Keys / Islamorada

Islamorada apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$76

Price per night from

$76

(3) Very Good 

29

**Winter Promo** Modern Executive Bay Club Condo with Pool & Beach

Florida Keys / Islamorada

Islamorada apartment

3 8 28 nights min

  • 3 bedrooms
  • sleeps 8
  • 28 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great condo, perfect location!” I have two small children and the condo was perfect and comfortable for the entire family. It was nicely remodeled. The pool and dock area were very nice. Security was visible and very friendly. The location was close t
…see more

Price per night from

$111

Responds fast!
avg. 2 hours 2 minutes

Price per night from

$111

(2) Excellent 

25

PALMS 314

Florida Keys / Islamorada

Islamorada apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Ask about children
“Wow, what a beautiful view” This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had "the window" in the master bedroom and in the
…see more

Price per night from

$80

Price per night from

$80

51

Islamorada Paradise

Florida Keys / Islamorada

Islamorada house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

Price per night from

$599

Price per night from

$599

(4) Very Good 

6

Islamorada 2-bedroom Condo

Florida Keys / Islamorada

Islamorada apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Fantastic Views” This 6th floor unit has all you need for a relaxing vacation. Close proximity to local attractions and fantastic Seafood Restaurants. The Hospital is one mile from the condo and has an excellent rehab and emergency. The complex h
…see more

Price per night from

$185

Price per night from

$185

(14) Excellent 

25

BROCK HAUS ON THE GULF

Florida Keys / Islamorada

Islamorada apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
“Absolutely Beautiful and convenient for boaters!” Our family stayed here for a week in late March. We had plenty of room and everything we needed was available. This is a gorgeous condo overlooking the Florida Bay. You get to see an awesome sunset eve
…see more

Price per night from

$225

Price per night from

$225

(17) Very Good 

35

FALL SPECIAL DISCOUNTED PRICING!!!

Florida Keys / Islamorada

Islamorada condo

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“The Best Keys Location” My family stayed at this lovely Futura Yacht Club Condo for three weeks this July. We have stayed at many other units in this complex over the years but this unit was one of the nicest we have seen. The unit has been remodel
…see more

Price per night from

$114

Responds fast!
avg. 3 hours 49 minutes

Price per night from

$114

(1) Excellent 

25

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Florida Keys / Islamorada

Islamorada villa

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$279

Price per night from

$279

25

FLAMINGO COTTAGE

Florida Keys / Islamorada

Islamorada house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet Friendly

Price per night from

$100

Price per night from

$100

21

Sunny Haven Islamorada

Florida Keys / Islamorada

Islamorada house

3 7 28 nights min

  • 3 bedrooms
  • sleeps 7
  • 28 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Price per night from

$474

Responds fast!
avg. 1 hour 8 minutes

Price per night from

$474

25

THE PALMS 405 - 93

Florida Keys / Islamorada

Islamorada apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$103

Price per night from

$103

26

Experience the Florida Keys like never before!!!

Florida Keys / Islamorada

Islamorada condo

2 6 30 nights min

  • 2 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$214

Price per night from

$214

(2) Excellent 

25

BEACON REEF 222

Florida Keys / Islamorada

Islamorada apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$146

Price per night from

$146

48

50 Schooner Bay

Florida Keys / Islamorada

Islamorada house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$722

Price per night from

$722

25

PALMS 402

Florida Keys / Islamorada

Islamorada apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$80

Price per night from

$80

(1) Excellent 

25

BEACON REEF 501

Florida Keys / Islamorada

Islamorada apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$110

Price per night from

$110