Madeira Beach Cabin Rentals & Beach Rentals with Swimming Pool - 83 Rentals Available.
83 Vacation rentals
Filters applied: Swimming pool

Kima 403 2bedroom Gulf Front Condo PRICELESS SUNSETS!
Madeira Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$205.00
from $205.00 / night

Enjoy a Florida Vacation in a beachfront condo!
Madeira Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 14 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$172.00
from $172.00 / night

Kima 101 BEACH FRONT with PRIVATE CABANA 2BR/2Bath
Madeira Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$205.00
from $205.00 / night

Kima 204 Direct Gulf Front in Madeira Beach
Madeira Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$258.00
from $258.00 / night

Kima 102 2bed/2bath Gulf Front Condo in Madeira Beach READY TO ENJOY!!
Madeira Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Air conditioning
$258.00
from $258.00 / night
Kima 503 Madeira Beach Front 2bd/2bath Condo Top Floor WHITE SANDY BEACHES!
Madeira Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$197.00
from $197.00 / night
Kima 205 Spacious 2bd/2bath Madeira Beach Gulf Front Condo Endless Views
Madeira Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$205.00
from $205.00 / night
2 BR, 2 BA Surf Song Resort Townhouse #343 -- Jun 13-20- Special $750/wk + fees
Madeira Beach Townhouse
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Nearest beach 30 mi
- Swimming pool
- Child friendly
$150.00
from $150.00 / night
Madeira Norte - Across from John's Pass Village - Ask about our Specials!!!
Madeira Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
Responds fast! Avg. 2 hours 34 minutes
$164.00
from $164.00 / night
Fall SALE $115/nt til 11/18 Gulf front partial view, Ktchn, Pool, Johns Pass
Madeira Beach Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$149.00
from $149.00 / night
231A Madeira Beach Yacht Club
Madeira Beach Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$95.00
from $95.00 / night
Madeira Bay Enjoy Sunrise Views from Balcony Overlooking Intracoastal Waterway
Madeira Beach Condo
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$230.00
from $230.00 / night
Gulf Beach Condo! 3 BR, Handicap & Tall equip'd
Madeira Beach Condo
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$258.00
from $258.00 / night
Walkable to Eats, Nightlife, & Madeira Beach! Ground Floor at Yacht Club!
Madeira Beach Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$90.00
from $90.00 / night
Waterfront and Walkable to Best Of Madeira Beach! 2 Blocks to the Sand!
Madeira Beach Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$90.00
from $90.00 / night
Beachfront Overlooking Madeira Beach- Walkable to Eats & Local Favs!
Madeira Beach Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 14 nights min
- Swimming pool
- Child friendly
- Air conditioning
$151.00
from $151.00 / night
Waterfront & Winter Retreat Family Vacay! Madeira Beach Local Fav!
Madeira Beach Condo
- 3 bedrooms 3
- 2 bathrooms
- sleeps 7 7
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$140.00
from $140.00 / night
Family Fun Poolside Stay! Walkable To Madeira Beach & Local Favorites!
Madeira Beach Condo
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$120.00
from $120.00 / night
Direct Madeira Beach Views and Sunsets Galore! Walkable to Best of Madeira!
Madeira Beach Studio
- Studio -1
- 1 bathroom
- sleeps 2 2
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$106.00
from $106.00 / night
Your search has been expanded 19.2 miles to include more rentals
4 Bedroom 2 Bath Bayfront, Pool, Gof, Canoe, More.
Tampa House - 19.2 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 4 nights min
- Swimming pool
- Child friendly
- Air conditioning
$315.00
from $315.00 / night
Beautifully updated Clearwater Condo- 20-25 Minutes to the Beach
Clearwater Condo - 8.6 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 1 night min
- Nearest beach 16 mi
- Swimming pool
- Child friendly
$189.00
from $189.00 / night
CLEARWATER LUXURY RESORT STYLE CONDO
Clearwater Condo - 10.4 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 2 nights min
- Swimming pool
- Ask about children
- Air conditioning
$144.00
from $144.00 / night
Vista del Mare by beachhouseFL New beachfront high end home! Last min deals
Indian Shores House - 4.3 miles away
- 6 bedrooms 6
- 7 bathrooms
- sleeps 22 22
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$801.00
from $801.00 / night
SUNSHINE HOLIDAY
St. Petersburg Manor house - 10.2 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,145.00
from $1,145.00 / night
Seashell Resort
Redington Beach Manor house - 0.1 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 13 13
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$1,145.00
from $1,145.00 / night
LUXURY WATERFRONT CONDO ON ISLA DEL SOL/St.Pete's
St. Petersburg Condo - 8.7 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 1 mi
- Swimming pool
Responds fast! Avg. 2 hours 14 minutes
$228.00
from $228.00 / night
Beautiful updated condo overlooking Tampa Bay
St. Petersburg Condo - 8.3 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 2 nights min
- Swimming pool
- Air conditioning
- Pet friendly
$86.00
from $86.00 / night
BEAUTIFUL HARBORVIEW GRANDE
Clearwater Condo - 11.5 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0.1 mi
- Swimming pool
$315.00
from $315.00 / night
Luxury Gulf/Pool Front/ Corner Unit
Indian Shores Condo - 3.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$148.00
from $148.00 / night
SEA GATE 506 Beach Front 3BED/2BATH Indian Shores Spacious Top Floor Condo
Indian Shores Condo - 4.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$221.00
from $221.00 / night
Dunedin Relax in our Updated condo
Dunedin House - 17.2 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 30 nights min
- Nearest beach 3 mi
- Swimming pool
- Child friendly
Responds fast! Avg. 1 hour 10 minutes
$69.00
from $69.00 / night
Paradise at Sunset Beach, Treasure Island
Treasure Island Condo - 4.5 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
Responds fast! Avg. 1 hour 10 minutes
$115.00
from $115.00 / night
ULTIMATE ST PETE BEACH FRONT RENTAL CONDO #101
St. Pete Beach Condo - 5.6 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 3 hours 12 minutes
$210.00
from $210.00 / night
Beachy "Margaritaville Pool home", 3 BR, 2 Bath
Clearwater House - 13.5 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 5 minutes
$487.00
from $487.00 / night
Beach Front Condo In Indian Rocks Beach
Indian Rocks Beach Condo - 7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Car not necessary
Responds fast! Avg. 2 hours 43 minutes
$210.00
from $210.00 / night
Breathtaking Water Views from Every Room - On the Beach
Clearwater Condo - 10.2 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$295.00
from $295.00 / night
*Fall through April now OPEN!* Beachfront, Full Views, 2/1, Ktchn, Pool*
North Redington Beach Condo - 1.9 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$161.00
from $161.00 / night
Sunset Beach Treasure Island Paradise OPEN APRIL 2020
Treasure Island Condo - 4.5 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Car not necessary
Responds fast! Avg. 1 hour 24 minutes
$109.00
from $109.00 / night
Gorgeous Hideaway on the Gulf of Mexico
Clearwater Condo - 10.2 miles away
- 1 bedroom 1
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$315.00
from $315.00 / night
Coconut Cabana 2/1 Cottage, sleeps 4, Two heated pools, Walk to Beach
Clearwater Cottage - 12.6 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Nearest beach 0.02 mi
- Swimming pool
- Child friendly
$212.00
from $212.00 / night
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