Vacation Rentals with Pool in Fiesta Key, FL: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Fiesta Key

Refine your search

Price per night

Amenity Filter

Rating

109 Best Vacation Rentals with Pool in Fiesta Key (Starting from $214)

Lime Tree Bay Resort
Lime Tree Bay Resort
Resort
Islamorada, FL, USA
2.7k from Fiesta Key center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Beach

61 Bedrooms54 Guests
8.6

Fabulous

2082 reviews

$247
Average price / night
Check Availability
Fishing and Boating Paradise with 30 Foot Boat Slip and Swimming Pool
Fishing and Boating Paradise with 30 Foot Boat Slip and Swimming Pool
Condo
Long Key, FL, 33001, United States
0.9k from Fiesta Key center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

42 reviews

$426
Average price / night
Check Availability
Ocean View Duplex Penthouse Retreat amenities: tennis court heated Pool Vista Key One
Ocean View Duplex Penthouse Retreat amenities: tennis court heated Pool Vista Key One
Apartment
Islamorada, FL, USA
6.5k from Fiesta Key center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay

1 Bedroom10 Guests
New to Booking
$880
Average price / night
Check Availability
A Pirates Great Escape ~ 3bed/2baths  Ocean View Boat Slip included
A Pirates Great Escape ~ 3bed/2baths Ocean View Boat Slip included
House
Layton, FL, 33001, United States
0.9k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.8

Exceptional

21 reviews

$477
Average price / night
Check Availability
Ocean View Penthouse Retreat amenities: tennis court heated Pool Vista Key Two
Ocean View Penthouse Retreat amenities: tennis court heated Pool Vista Key Two
Apartment
Islamorada, FL, USA
6.5k from Fiesta Key center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$582
Average price / night
Check Availability
Ocean front gated privacy with 3 bedrooms and protected boat slip.
Ocean front gated privacy with 3 bedrooms and protected boat slip.
Condo
Layton, FL, 33001, United States
0.9k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

57 reviews

$447
Average price / night
Check Availability
Ocean View Two Duplex Penthouses Retreat amenities: tennis court heated Pool Vista Key
Ocean View Two Duplex Penthouses Retreat amenities: tennis court heated Pool Vista Key
Apartment
Islamorada, FL, USA
6.6k from Fiesta Key center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay

1 Bedroom18 Guests
New to Booking
$1388
Average price / night
Check Availability
Spectacular Views of Ocean with Pool and Boat Slip.
Spectacular Views of Ocean with Pool and Boat Slip.
House
Long Key, FL, 33001, United States
1.2k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$543
Average price / night
Check Availability
Florida Keys Getaway with Stunning Ocean Views
Florida Keys Getaway with Stunning Ocean Views
House
Layton, FL, USA
7.0k from Fiesta Key center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach

3 Bedrooms10 Guests
New to Booking
$909
Average price / night
Check Availability
One Of A Kind Ocean Front With Boat Slip
One Of A Kind Ocean Front With Boat Slip
Condo
Layton, FL, 33001, United States
2.2k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Elevator, Fireplace, Free Parking, Heater, Hot Tub

3 Bedrooms8 Guests
9.8

Exceptional

57 reviews

$383
Average price / night
Check Availability
Waterfront Wonder
Waterfront Wonder
House
Islamorada, FL, USA
7.3k from Fiesta Key center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

6 Bedrooms12 Guests
New to Booking
$1007
Average price / night
Check Availability
Private Waterfront Home, Heated Pool, Beach, Tiki w/Grill, Dock, Kayaks, Sunset
Private Waterfront Home, Heated Pool, Beach, Tiki w/Grill, Dock, Kayaks, Sunset
House
Long Key, FL, 33001, United States
2.7k from Fiesta Key center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Extra Bed, Fireplace, Free Parking, Heater

3 Bedrooms10 Guests
10.0

Exceptional

103 reviews

$1473
Average price / night
Check Availability
Beachfront Villa at Islamorada BY THE GLAMHOMES
Beachfront Villa at Islamorada BY THE GLAMHOMES
Villa
Islamorada, FL, USA
8.7k from Fiesta Key center

Internet, View, Private Beach, Oceanfront, Sports/Activities, Ocean View, Fireplace/Heating

4 Bedrooms6 Guests
1.0

Review score

1 reviews

$7615
Average price / night
Check Availability
Home w/ 2nd Story Pool & Spa w/ Open Water Views
Home w/ 2nd Story Pool & Spa w/ Open Water Views
House
Layton, FL, 33001, United States
2.7k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

76 reviews

$1480
Average price / night
Check Availability
Matecumbe Resort
Matecumbe Resort
Apartment
Islamorada, FL, USA
9.4k from Fiesta Key center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals, Beach, Places to stay

32 Bedrooms26 Guests
8.4

Very Good

332 reviews

$214
Average price / night
Check Availability
A fisherman's Dream, Ocean-front Condo.  Call Richard at 207-985-3600 to discuss
A fisherman's Dream, Ocean-front Condo. Call Richard at 207-985-3600 to discuss
Resort
Long Key, FL, 33001, United States
2.9k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
New to Booking
$246
Average price / night
Check Availability
Beach Residence Private overwater dock Heated Pool Mahi Key
Beach Residence Private overwater dock Heated Pool Mahi Key
House
Islamorada, FL, USA
9.6k from Fiesta Key center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$1282
Average price / night
Check Availability
Beautiful Pool Home Located in a Quiet Neighborhood
Beautiful Pool Home Located in a Quiet Neighborhood
House
Long Key, FL, 33001, United States
3.0k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
New to Booking
$649
Average price / night
Check Availability
3 Bedroom / 2.5 Bathroom Layton Home with Pool & Dockage
3 Bedroom / 2.5 Bathroom Layton Home with Pool & Dockage
House
Layton, FL, 33001, United States
3.2k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
New to Booking
$428
Average price / night
Check Availability
3-bedroom, 3-bath Canal front home with private pool in Islamorada, Florida Keys
3-bedroom, 3-bath Canal front home with private pool in Islamorada, Florida Keys
House
Islamorada, FL, 33036, United States
5.5k from Fiesta Key center

AC, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, Patio, Pool

3 Bedrooms10 Guests
New to Booking
$384
Average price / night
Check Availability
A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool
A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool
House
Islamorada, FL, 33036, United States
5.5k from Fiesta Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave

3 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$571
Average price / night
Check Availability
Coastal Studio Getaway – Second Floor with Partial Water Views
Coastal Studio Getaway – Second Floor with Partial Water Views
Apartment
Islamorada, FL, 33036, United States
5.6k from Fiesta Key center

AC, Balcony, Elevator, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

1 Bedroom3 Guests
9.2

Superb

5 reviews

$348
Average price / night
Check Availability
Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home
Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home
House
Islamorada, FL, 33036, United States
5.6k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms12 Guests
10.0

Exceptional

21 reviews

$668
Average price / night
Check Availability
\"Our Happy Place\" Paradise in Islamorada with Heated Pool and 90 ft Dock
\"Our Happy Place\" Paradise in Islamorada with Heated Pool and 90 ft Dock
House
Islamorada, FL, 33036, United States
5.6k from Fiesta Key center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$495
Average price / night
Check Availability
Waterfront Oasis 2Mins2BeachTons dockage VERY Private Immediate ocean/bay access
Waterfront Oasis 2Mins2BeachTons dockage VERY Private Immediate ocean/bay access
House
Islamorada, FL, 33036, United States
5.8k from Fiesta Key center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

5 Bedrooms12 Guests
10.0

Exceptional

72 reviews

$1052
Average price / night
Check Availability
You will never want to leave
You will never want to leave
House
Islamorada, FL, 33036, United States
5.8k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Elevator, Fireplace, Free Parking, Heater, Internet

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1031
Average price / night
Check Availability
Beautiful 4/3, pool home in lovely White Marlin beach, Islamorada, FL
Beautiful 4/3, pool home in lovely White Marlin beach, Islamorada, FL
House
Islamorada, FL, 33036, United States
5.9k from Fiesta Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

21 reviews

$586
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Fiesta Key.

Where to stay in Fiesta Key? Best neighborhoods & areas

Fiesta Key Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 109 verified vacation rentals with a pool in Fiesta Key. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Fiesta Key vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $214 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Fiesta Key offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Fiesta Key welcome pets. Currently, 27 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Fiesta Key often include additional outdoor features such as Pool, View, and Wellness Facilities. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Fiesta Key offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.